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Margaritaville Resort Key West with palm trees wrapped in Christmas lights at night during Florida vacation

14-Day Florida Road Trip Itinerary: Detroit to Keys ($2,919 Total Cost) – Every Hotel Named

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Table of Contents

14-Day Florida Road Trip Itinerary: Detroit to Keys ($2,919 Total Cost) – Every Hotel Named

Plus: How to Gift the Entire Trip (So Everyone Has Something to Unwrap)

Margaritaville Resort Key West with palm trees wrapped in Christmas lights at night during Florida vacation

Want to gift your teenagers an unforgettable Florida road trip this Christmas but worried about having nothing under the tree? This itinerary is designed so the whole family can chip in—and everyone has something to unwrap. Here’s your 14-day Florida road trip from Detroit to the Keys with every hotel named, real out-the-door prices, and a gift list for each day.


💰 Money-saving trick: Before you book, read our Florida Travel Deals & Discounts guide. Example: Go City Pass saves you $400+ if you’re hitting 5+ attractions. We break down which passes actually save money (and which are tourist traps).


📊 PERSPECTIVE CHECK: The average American family spends $3,600-$4,000 on Christmas gifts. This entire 2-week Florida vacation costs $2,919 – less than what most families spend on toys that end up in the closet by February. Add the Go City Pass ($876) and you’re still under $4,000 – but now you’re giving memories instead of stuff.

How Much Does a 2-Week Florida Road Trip Cost? ($2,919 Breakdown)

Here’s exactly what this 14-day Florida road trip costs: $2,919 total for a family of 4 (2 adults, 2 teens). These are real, researched prices with taxes included – not ballpark guesses. I checked every hotel rate for February 2026 dates, calculated actual gas costs, and budgeted realistic daily food spending. Your costs will vary based on travel dates, but this gives you an honest baseline.


🚗 Gas: $448

  • Route: Detroit → Florida Keys → Detroit
  • Total miles: ~3,200 miles round-trip
  • Vehicle: 25 MPG average
  • Gas price: $3.50/gallon (averaged between Michigan $3.05 and Florida $2.98)

🍔 Food: $980 (14 days, family of 4)

Want to slash this even lower? Our cheap eats guide shows you exactly where to find the best deals at every stop—we’re talking $5 family meals, loaded mashed potato bowls, and quality food that won’t leave you feeling gross. You could easily cut this budget by $300 or more.

  • Breakfast: $10/day (hotel breakfast or grocery store)
  • Lunch: $20/day (fast food, picnics, food trucks)
  • Dinner: $40/day (casual sit-down or takeout)
  • Daily total: $70 × 14 days = $980

💡 Money-saving tip: Pack a portable travel grill for park cookouts. We saved $200+ grilling hot dogs and burgers instead of eating out every night.

🏨 Hotels: $1,441 (13 nights)

  • Price range: $68-$188/night depending on location
  • What you get: Clean beds, working bathrooms, free parking (usually)
  • What you DON’T get: Instagram lobbies, luxury amenities

These aren’t luxury chains, but they’re affordable enough to make this trip actually happen. If you want to upgrade specific nights (Key West, beach towns), expect to add $50-100+/night.

✅ Every hotel is named and linked in the day-by-day sections below so you can check reviews yourself.


Cost CategoryTotalWhat’s Included
🚗 Gas$4483,200 miles round-trip, averaged fuel prices
🅿️ Park Entry & Parking Fee$50Fort Zachary Taylor State Park $6, Fort De Soto Park: $6/vehicle, Beach parking meters in some cities: $5-10
🍔 Food$98014 days, breakfast/lunch/dinner for family of 4
🏨 Hotels$1,44113 nights, budget chains with taxes included
TOTAL$2,919Everything except activities
➕ Go City Pass (optional)$87620+ attractions across multiple cities
WITH PASS$3,795Fully loaded vacation

🎉 What $2,919 Gets You:

This is a complete vacation – not a bare-bones “cover the basics and figure out the rest” trip. Every day includes:

  • Free beaches, parks, and scenic drives
  • Wildlife spotting (gators, dolphins, manatees)
  • Historic sites and boardwalks
  • Sunrise/sunset spots
  • Unique roadside stops

You could spend $0 on activities and still have an incredible trip. The paid attractions (airboat tours, theme parks, museums) are totally optional upgrades.

Optional Upgrade: Go City Pass for 20+ Florida Attractions ($876)

Your $2,919 baseline trip is already packed with free beaches, wildlife, and scenic drives. But if you want to add paid attractions like Kennedy Space Center, theme parks, airboat tours, and dinner shows, the Go City Pass can save you serious money.

Pass options: 2, 3, 4, or 5 consecutive days once activated. We recommend the 2-day pass ($219/person, $876 for family of 4) for this itinerary because you can knock out most attractions in Orlando on Day 5 and Cocoa Beach/Kennedy Space Center on Day 6. Need more days? The 5-day pass gives you flexibility across Miami, Tampa, and beyond.

Here’s the math: If you’re planning to do 3+ paid activities, this pass pays for itself. It covers 20+ attractions across Orlando, Miami, Tampa, and Daytona – cities you’re already visiting on this itinerary.

💭 Is the Go City Pass worth it for this trip?

Get it if:

Skip it if:

  • You’re happy with free beaches, parks, and scenic drives
  • Your family isn’t into theme parks or structured tours
  • You want maximum flexibility to choose activities day-by-day

Bottom line: If you plan to do 5+ activities on the pass, you’ll save $400-500. If you only do 2-3, you’ll break even. If you do fewer than 3, skip it and pay as you go.

💰 Updated Budget with Go City Pass:

  • Baseline trip: $2,919
  • Go City Pass: $876
  • New total: $3,795

Still under $4,000 – and now you’ve got Kennedy Space Center, dinner shows with meals included, free Miami transportation, and 20+ other attractions unlocked. Compare that to the average family Christmas spending ($3,600-$4,000 on stuff), and you’re giving experiences instead of toys.

🎟️ Where You’ll Use This Pass on the Itinerary:

Pro tip: The pass works for 2 consecutive days once activated, so plan your paid activities back-to-back. Our Orlando Attraction Pass Planning Guide shows you how to hit 8 attractions in one day.

14-Day Florida Road Trip Itinerary at a Glance

This itinerary is designed for teenagers who want to see it all – it’s fast-paced and action-packed, not a sit-and-relax vacation. You’ll cover 3,200 miles in 14 days with a new experience every single day.

DayLocationDrive TimeBudgetHighlights
Jump to day 1Savannah, GA13.5 hrs from Detroit$152River Street, ghost tours, Southern food
Jump to day 2SavannahFull day in city$152Forsyth Park, Historic District, Tybee Island
Jump to day 3St. Augustine2.5 hrs south$138Spanish fort, lighthouse, cobblestone streets
Jump to day 4Daytona Beach1 hr south$138Drive on beach, boardwalk, pier
Jump to day 5Orlando area1 hr west$138Theme park OR free Disney Springs + Go City attractions
Jump to day 6Cocoa Beach / Kennedy Space Center1.5 South$199Rockets, beach pier, wildlife refuge
Jump to day 7Miami3 hrs south$183South Beach, Wynwood Walls, Little Havana
Jump to day 8Florida Keys day trip3 hrs to Key West$183Overseas Highway, feed tarpon, Key West sunset
Jump to day 9Everglades & NaplesCross to west coast$258Airboat tour, gator spotting, Marco Island, Tin City
Jump to day 10Venice / Caspersen BeachStay in area$258Shark tooth hunting, flamingos at Jungle Gardens
Jump to day 11Sarasota & St. Pete30 min north$203.50Hand-feed flamingos, Fort De Soto shelling, sunset
Jump to day 12Clearwater / John’s Pass20 min north$196Beach pier, dolphin watching, boardwalk
Jump to day 13Tarpon Springs / Start drive home30 min + 6 hrs north$160Greek sponge docks, Weeki Wachee mermaids, drive to Georgia
Jump to day 14Drive home13–15 hrs$70Finish drive to Detroit

🎁 Florida Vacation Packing List: Gift Ideas for the Whole Family

Not sure what to wrap? Every item below gets used on this trip – nothing sits in a closet. We’ve organized by price point so different family members can chip in: parents handle the big stuff, grandparents grab medium items, and aunts/uncles can pick smaller essentials. By Christmas morning, the whole trip is covered.

Big Gifts

Travel & Transportation:

  • Luggage set – Spinner wheels (360-degree) are a game-changer you don’t appreciate until you have them. Hotel trips mean multiple bags – your luggage, yes, but also snacks, drinks, chargers, coats, the stuff you forgot. With spinners: pull the handle up, stack your second bag on top (thread handles through the luggage handle), roll it all with ONE hand. Try making a sharp elevator turn with regular wheels and your hands full – nightmare. 360 spinners? Effortless. This is an investment piece you’ll use for years. So worth it.
  • Thule roof box/carrier – Game-changer for staying organized. Stash the things you won’t need for a few days (extra jackets, beach gear for later stops, camping chairs) and keep your daily stuff accessible. Even with just 2 people, it beats digging through a packed trunk every stop.
  • America the Beautiful annual pass – $80 for the whole year. Covers Castillo de San Marcos, Canaveral National Seashore, Fort Zachary Taylor, plus every national park in the U.S. Pays for itself on this Florida trip, and now you have 12 months to squeeze in more adventures. It’s like having a reason built-in to take another road trip. You’ll find yourself planning weekends around it.

Tech & Electronics:

  • GoPro – Because some moments need both your hands AND video proof. Mount it to your snorkel mask to film underwater at Fort Zachary. Hand-feed those MASSIVE tarpon at Robbie’s Marina (we’re talking 4-8 foot fish over 200 pounds – you’re gonna yell, trust me). Your phone can’t handle this. GoPro can. Those reaction videos? Priceless.
  • High-capacity portable charger – Because your phone will die at the absolute worst moment, guaranteed. Right when the jugglers start at Key West sunset? Dead. Can’t find your car? Dead. Need to call the family who wandered off? Dead. I’m the king of this happening. Just get the portable charger, keep it in your bag, save yourself the stress. Worth every penny.
  • Dash cam – For that Florida panther we keep looking for, the giraffe sticking its head IN your car at the safari, the cool car you passed, or proof of what happened while someone was napping. Captures everything you don’t have time to grab your phone for.
  • Audible membership – Audiobooks for the 13-15 hour drives home

Beach & Activity Gear:

  • Large cooler – Ice, drinks, snacks
  • Portable travel grill – Family time without the restaurant rules. Grill at state parks, picnic tables at beaches, or hotel parking lots. Kids can run around, everyone’s more relaxed, and you’re making memories instead of just eating. Plus, you’ll save hundreds on dinners over 2 weeks.
  • Beach cart – Beach cart – Trust me on this. Without it, you’re either leaving the cooler in the car OR you’re trudging through sand like you’re training for a marathon, arms full, questioning your life choices. With the cart? Throw everything in, roll it to your spot, actually ENJOY the beach. Worth every penny.
  • Mini photo printer – Turn your trip into instant postcards for the family who helped pay for it. Print pictures throughout the trip and mail them back – the kids snorkeling with the gear Aunt Beth bought, cooking on the grill Grandpa gave you, hunting shark teeth with the sifter from Uncle Mike. Way better than a generic thank-you note, and the kids will love being involved.
  • Polaroid camera – Old-school road trip vibes in the best way. Takes you back to when families grilled at roadside parks and made memories instead of just content. Black and white film makes every moment look vintage and intentional. Physical photos you can actually hold, share, and stick on the fridge when you get home.

    💡 Random but trust me: Take a Polaroid in the hotel room on arrival. My favorite photo from our first ocean trip isn’t from the beach – it’s my kids in the hotel room, one on the bed, one in the mirror, just EXCITED to be somewhere new. That Day 1 energy before they’re tired and over it? You can’t get it back. Capture it while it’s real.

Medium Gifts

Snorkeling & Water Activities:

  • Snorkel mask – Get the full face mask style – easier to breathe, better visibility, way less water up your nose. Pick up anti-fog spray too. Fins listed here, but real talk: skip them unless you’re already comfortable using them. The snorkeling spots on this trip don’t require fins, and they’re awkward if you’ve never used them before.
  • Waterproof phone pouch – Not the most exciting purchase, but you’ll be SO glad you have it. Shark tooth hunting? Your phone stays dry and sand-free while you’re knee-deep in water. Airboat tour? Take gator photos while water’s splashing everywhere. Beach days? No more leaving your phone in the car or worrying about sand getting in every crack. Worth every penny.
  • Water shoes – Not optional. Fort Zachary Taylor’s snorkeling? You’re standing on sharp rocks to rest. Marco Island? More shells than sand – your feet will hate you without protection. Shark tooth hunting? Broken shells hidden in the sand everywhere. Trust me, water shoes turn painful beaches into enjoyable ones.

Car Comfort:

  • Neck pillows – Look, they’re not cool. But neither is showing up to the beach with your neck locked up from sleeping against the car window for half of Georgia. Long drive days are brutal without these. You’ll think they’re silly right up until you’re trying to get comfortable and your neck starts hurting – then they’re suddenly genius. Small price for not starting your vacation in pain.
  • Travel trays – Game-changer for long drives. Fits a laptop (yes, really), so you can catch up on work or homework during the passenger stretches. Eating, reading, planning the next stops, tablets, playing games – basically anything except driving and sleeping becomes way easier with a stable surface. No more balancing snacks on your lap or papers sliding everywhere. For 13+ hours in the car? Absolutely worth it.

    💡 Pro tip: Most libraries let you check out mobile hotspots like a book – free wifi for the road so laptops actually work anywhere.
  • Headphones – By hour 10 of driving, everyone needs their own audio situation. You need YOUR music to stay awake and focused. The kids need their music so they don’t have to hear you belt out the chorus. Win-win. Individual headphones = sanity for the whole car. Trust me on this.

Beach Essentials:

  • Beach towels – You need these, obviously. Get quick-dry ones so they don’t stay damp and smelly in your car. One per person. Don’t use hotel towels – most places charge if you take them to the beach.
  • Beach blanket – waterproof & sandproof – Yes, you need this ON TOP OF having towels. The blanket goes down on the sand first, then you put your stuff on it, THEN you use your towel for drying off. You’re not laying your drying towel directly on sticky sand, right? Get a big one – nobody likes being squished together. Plus, you’ll use this for way more than just this trip. Picnics, concerts, camping – it’s not a one-trip purchase.
  • Beach chair – Not everyone needs one, but if you’re even questioning it, just get it. This trip puts you on beaches multiple times (Daytona, Fort De Soto, Caspersen, Marco Island, Clearwater) – a chair makes those days way more comfortable. Don’t like the low beach chairs that sit in the sand? A regular camping/bag chair works great too. Sitting on towels gets old fast when you’re doing beach days for 2 weeks.

Shark Tooth Hunting Gear (Day 10):

  • Shark tooth scoop/sifter – Budget version works for trying it once. But here’s the thing: shark tooth hunting is ADDICTIVE. I went once and now it’s on my list every Florida trip. If you think there’s even a chance you’ll love this, get the better sifter. It’s night and day – keeps you out longer, easier on your arms, just works better. The cheap one finds teeth too, but if you’re spending an hour+ hunting, the upgrade is golden. Don’t cheap out if you’re prone to new obsessions.
  • Shark tooth container – Get a hard waterproof phone case with a neck strap. Wear it, drop teeth in as you find them, snap it shut, keep hunting. This is a LIFE-SAVER. You do not want to walk back to shore every time you spot a tooth – you’ll be doing that every 30 seconds once you get good at this. Keep everything around your neck, stay in the water, stay in the zone. You need nothing else.

Organization & Packing:

  • Packing cubes set – End the suitcase chaos. Nothing’s worse than your underwear just hanging around with everything else, digging through piles to find one shirt, and repacking a disaster every morning. These organize by person or type (beach gear, sleepwear, basics), compress everything down, and make finding stuff actually possible. With 13 hotel switches on this trip, the organization alone is worth it.
  • Binoculars – We were SO glad we had these when we spotted wild boar on a scenic drive. Dolphins swimming in the distance at John’s Pass? You’ll see details you’d completely miss. Weird Florida birds you’ve never seen before? Actually identify them. Gators sunbathing far off on the Tamiami Trail? Zoom in without getting too close. Makes wildlife spotting way more exciting when you can actually SEE what you’re looking at.
  • Picnic kit – You’ll use this for everything: park grilling, hotel room meals, car lunches, beach snacks. Way better than eating out of containers with plastic forks for 2 weeks. Real plates and utensils make food actually enjoyable instead of just functional. Gets used constantly when you’re doing budget-friendly meals throughout the trip.

Small Gifts

Sun Protection:

  • Reef-safe sunscreen – This is Florida. The sun hits different. I work outside for a living and I STILL get burnt down there. Pack this before you go – it’s way cheaper at home than buying it at a beach shop, and you won’t be scrambling to find it when you’re already red. Get reef-safe for snorkeling spots (Fort Zachary Taylor requires it). Apply more than you think you need. Florida sun is no joke.
  • After-sun lotion – What works for me (everyone’s different, not medical advice): Apply it constantly – like every time you think of it. Every 30 minutes? Perfect. Every 3 hours? Think of it more! The more I apply, the faster burns fade. Bad burns gone in 1-2 days instead of a week. I don’t even wait until I’m burnt – I apply after sun exposure to stay ahead of it. Has worked every Florida trip. Serious burns? See a doctor, not a blog.
  • Polarized sunglasses – The difference between seeing reflections and seeing THROUGH the water. Spot tarpon, manatees, fish swimming below – stuff you’d completely miss with regular sunglasses. Shark tooth hunting becomes so much easier when you can actually see into the water. And yeah, they help with windshield glare on drives too, but trust me – the underwater spotting is why you need polarized.

Beach & Water Gear:

  • Sand dollar/shell storage containers – Sand dollars are incredibly fragile – toss them in a regular bag and they’ll shatter. When you find your first whole sand dollar (it’s magical, trust me), you’ll want it home intact. These containers protect fragile finds from breaking during travel. Worth it to preserve what you worked so hard to find. Nothing sadder than unwrapping broken pieces of what was perfect on the beach.
  • Shell collection bag – Shell collection bag (mesh or canvas) – Shells hold up well and you’ll want to bring some home. Lingerie washing bags work great – zip closure, mesh, good size. Just need mesh that zips.
  • Pop-up changing room – Pop-up changing room / privacy shelter – Traditional changing tents are a little expensive. We found these portable privacy shelters that work just as well for way less. Nice to have after beach days – change out of wet swimsuits, dry off, get into dry clothes without doing car-door gymnastics in a parking lot. You can get the fancy pop-up version or save money with these. Both work, one’s just way more affordable.

Car & Travel:

  • Small cooler – Because you’re not dragging the big cooler through sand to your beach spot. This is your portable beach cooler – a few drinks, some snacks, ice packs, done. Light enough to carry or toss in the beach cart. Keeps everything cold for your beach hours without the hassle of a massive cooler. The big one stays in the car, this one comes with you. Worth it for cold drinks all day.
  • Reusable ice packs – So you don’t have to track down ice every morning or deal with water from melted ice making everything in your cooler soggy. Freeze these overnight at the hotel (or just put them on the top shelf of the mini fridge if there’s no freezer – they’ll stay cold enough for most days). Throw them in your cooler, they stay cold all day. No mess, no ice runs, no wet food. Simple upgrade that makes daily cooler packing actually tolerable.
  • Car trash can – Keep car clean for 14 days
  • Multi-port car charger – Guaranteed: everyone gets in the car at the same time with a dead phone. No fighting over the single charging port – get enough for everyone to plug in at once. Long drives become charging time so you’re not stopping with dead devices. Cheap fix for a guaranteed daily problem. One port per person minimum.
  • Vacuum seal bags with pump – Compress clothes, save luggage space

Daily Essentials:

  • Water bottle with lid + Holder – One per person, and yes, the holder matters. You don’t want to carry your bottle everywhere or set it down in sticky ocean sand. Get bottles WITH LIDS (not open-top) – beach spray, sand, airboat splash, car dust – everything ends up in an open bottle. Clip the holder to your bag, keep hands free, keep your water clean. Simple but essential.
  • Day bag – Get a crossbody/sling bag for daily carry (sunscreen, band aid, ibuprofen, snacks, phone, wallet) AND a foldable backpack that clips on until needed. The crossbody handles everyday essentials. The foldable backpack? That’s for when you buy a few things, need to stash a sweatshirt for later (Mallory Square sunset gets breezy!), or any shopping happens. Keeps it clipped away until you actually need the space, then boom – instant extra bag.
  • Travel wallet – Forget the crossbody purse – get one of those slim clip-on wallets that tucks in your pocket. Clips to your waistband so you can’t lose it, holds your essentials (ID, credit cards, cash), and it’s discrete instead of bulky. No purse hanging off you at the beach or bouncing around at Mallory Square. Just what you need, clipped secure, out of the way.
  • Cooling fan – Blows cold air or just air You can get regular portable fans that blow air (totally fine, does the job), or you can go WILD with the ones that actually blow COLD/air-conditioned air. Those things are incredible – the technology is insane. If you run really hot or you’re a gadget person, the cold air version is worth it. Everyone else? Regular fan works perfect for humid Florida days.
  • Air mattress – Game-changer for hotel nights. Two beds, four people usually means sharing. Teenagers and tweens do NOT want to share beds anymore. Bring an air mattress – everyone sleeps better, nobody’s cranky in the morning, and it packs down small in the car. Inflates fast, deflates flat, totally worth the space.
  • Umbrella – Compact umbrellas are great for carrying around ‘just in case.’ Full-size umbrellas are for Florida’s actual afternoon downpours that come out of nowhere and drench everything in 30 seconds. If you’re just worried about a drizzle, compact works. If you’ve seen Florida rain before (or want to be prepared), go full-size. Those storms don’t mess around.

Gift Cards (Easy Gifting / Any Amount)

Perfect for people who “don’t know what to get” or live far away:

Transportation:

  • Gas gift cards – Check your credit card or bank rewards first – many let you redeem points for gas cards at no cost. Free gas for your 3,200-mile round trip? Yes please. Even if you’re paying cash, gas cards make great gifts from family members chipping in. Grandparents can give $50 in gas cards – practical, actually helps, and way better than another toy.
  • Southwest Airlines gift card – This trip is designed for road-tripping, but families can fly into Orlando or Miami and rent a car instead (skip Savannah/St. Augustine or adjust the route). If flying, airfare is your biggest cost – gift cards from family make a huge dent. $100-200 per person from different relatives = most of your flights covered. Southwest has no change fees if plans change.

Food:

  • Fast food multi-restaurant gift cards – Smart addition to your budget eating plan. Fast food is way cheaper than sit-down restaurants, and with gift cards, it’s practically free. Drive-thru breakfast before hitting the road? Lunch between attractions? Quick dinner after a long beach day? Fast food cards let you eat out affordably throughout the trip. Great gift from family members who want to contribute.
  • Restaurant-specific cards – When family wants to share something they loved. Grandparents gifting the Savannah riverboat dinner cruise they still remember. Friends who insist you try that specific Greek bakery in Tarpon Springs. The aunt who wants you to experience Mallory Square sunset with dinner they thought was perfect. These let them gift the exact moment they want you to feel. Check each day’s “Where to Eat” section for restaurants worth experiencing.

Activities:

  • Individual attraction tickets – Linked throughout each day’s section
  • Go City Pass – Covered in detail above

Stocking Stuffers & Last-Minute Adds

Snacks & Hydration:

  • Road trip snacks – Chips, jerky, trail mix, assorted granola bars – the essentials. Stock up at home (way cheaper than gas stations). Granola bars work for quick breakfasts, and those variety packs of donuts are great for a few mornings when you just need to grab-and-go. Keep a variety in the car for emergency hunger, long drives, or beach days.
  • Exotic snack box: Exotic snack box – Road trip entertainment disguised as food. Get a big international sampler box (snacks from around the world) and make it a car game. Try something new every hour, rate it, argue about flavors, record reactions. Turns a 13-hour drive into ‘let’s try the next weird thing!’ instead of ‘are we there yet?’ The snacks themselves? Hit or miss. The entertainment value? Totally worth it.
  • Water flavor packets – Makes hydration actually happen. Florida heat + full beach days = teens need more than plain water. These add electrolytes and vitamins, not just flavor. Prevents the mid-afternoon crash, tastes good enough that they’ll actually drink their water, and way cheaper than buying Gatorade at every stop. Small packets, big difference in how everyone feels.

Practical Essentials:

  • Ziplock bags – Gallon and quart sizes for wet swimsuits, sandy items
  • Hand wipes – Sticky fingers, sandy hands
  • Hand Sanitizer – Beach bathrooms, rest stops
  • First aid basics – Bandaids, pain reliever, antibiotic ointment – the basics for non-emergency stuff. Way cheaper and faster than finding a store mid-trip when someone needs something NOW. Pack it once at home, use it every trip. Saves money and hassle.
  • Dramamine – Motion sickness for car and boat rides
  • Portable door lock – You don’t need it until you suddenly do. Hotel break-ins aren’t the real concern – it’s housekeeping not knocking loud enough, or that rare (but real) situation where the hotel double-books and someone walks in with a key thinking it’s their room. This blocks entry from inside no matter who has a keycard. Peace of mind, especially for families with teenagers who want privacy.

Entertainment:

💡 Smart Gifting Strategy:

Give experience gifts alongside physical items for maximum Christmas morning impact:

  • Wrap the snorkel gear with a card saying “Day 8: Snorkel with tropical fish at Fort Zachary Taylor, Key West”
  • Wrap the shark tooth scoop with “Day 10: Hunt prehistoric shark teeth at Caspersen Beach”
  • Wrap binoculars with “Spot dolphins at John’s Pass, gators in the Everglades, and manatees at wildlife refuges”
  • Wrap the GoPro with “Capture airboat rides, underwater snorkeling, and beach memories”
  • Print individual day descriptions and wrap them separately so everyone opens activities all morning

This way you have physical items under the tree AND the excitement of planning what’s coming.

Fort De Soto beach clear water shallow water

What to Expect in Each Day Below:

Every day includes a budget breakdown, named hotels with real prices, free activities, optional paid add-ons, and packing tips. We’ve mapped two different routes (down and back) so the scenery never repeats.

Wildlife note: When we mention feeding animals (tarpon in Islamorada, flamingos in Sarasota), these are facility-run activities only – we never recommend feeding wildlife in the wild.

Day 1: Savannah Georgia – Where to Stay & Evening Activities (Budget: $152)

Savannah

How far is Savannah, GA (your starting point)?

Quick reality check: Savannah is 13-15 hours from Detroit. Here’s how far it is from other starting points if you’re adapting this trip:

Start city → SavannahApprox. miles (one-way)Typical no-stop drive time
Detroit, MI~880–980 mi~13–15 hrs
Chicago, IL~950–1,000 mi~15–17 hrs
New York, NY~780–860 mi~12–14 hrs
Cleveland, OH~730–800 mi~11.5–13 hrs
Indianapolis, IN~760–820 mi~12–13 hrs
Washington, DC~560–620 mi~8.5–10 hrs
Nashville, TN~490–520 mi~7.5–9 hrs
Charlotte, NC~240–270 mi~3.5–4.5 hrs

💡 Can’t drive 13+ hours in one day? Split it into two days and stay somewhere in Kentucky or Tennessee (adds ~$80-100 for an extra hotel night). Or fly into Savannah and start the trip there – you’ll miss the long drive but save time.

Day 1 Plan: Arrive & Explore

Arrival timing: You’ll arrive late afternoon/evening after a long drive. Don’t overschedule – you’ll be exhausted.

Evening activities:

  • Check into hotel (see options below)
  • Walk River Street for dinner and people-watching
  • Optional: Evening ghost tour if you’re energized (book with code RTOWL for 10% off)

💰 Budget tip: Grab fast food or drive-thru before arriving in Savannah to save $20-30. Then just buy pralines from River Street Sweets ($5-10) to get a taste of the city. Save a nice sit-down dinner for tomorrow when you have more time.


Where to Stay in Savannah (2 Nights)

📅 Book 2 nights here (Days 1 & 2) so you don’t have to pack up tomorrow. You’ll leave for St. Augustine on the morning of Day 3.

All prices include taxes and are based on February 2026 bookings.

Budget Options (Under $100/night)

OYO Hotel Savannah GA Hwy 17 – $82/night
Budget-friendly, about 15-20 minutes from Historic District. Basic but gets the job done.

Inn on 17 – $84/night
Basic but cheap, about 15-20 minutes from Historic District.

💡 The tradeoff: You’ll save $50-70/night on the room, but you’ll need to Uber into Historic District ($10-15 each way) or find street parking when you drive downtown to explore. Still cheaper overall, just less convenient than walking out your hotel door. Need to find street parking in Historic District? Use SpotHero to pre-book affordable spots.

Best Location (Walk to Everything)

These hotels put you IN the Historic District – walk to River Street, Forsyth Park, and all the squares:

Best Western Savannah Historic District – $142/night 👈 Our pick for best value
Walkable to everything, reliable chain hotel, solid reviews. This is the sweet spot between price and location.

AC Hotel Savannah Historic District – $172/night
Modern Marriott property, stylish rooms, walk to River Street.

Homewood Suites by Hilton Savannah Historic District/Riverfront – $183/night
Riverfront location, suites with full kitchens, free breakfast.

Staybridge Suites Savannah Historic District – $174/night
Suite-style rooms with kitchenettes, great for families.

Unique Historic Properties

Want the full Savannah experience in a historic building?

The Marshall House – $265/night
Historic hotel known for paranormal activity – stay in a haunted room if you dare. One of Savannah’s most iconic properties.

The Drayton Hotel – $314/night
Stylish boutique hotel with rooftop views overlooking the city.

Reliable Chain Hotels (For Points Collectors)

Earn points and enjoy familiar brands:

Hampton Inn Historic District – $141/night
Reliable Hampton quality, free hot breakfast, walking distance to River Street. Earn Hilton Honors points.

Holiday Inn Express Historic District – $134/night
Consistent IHG brand, free breakfast, earn IHG Rewards points.

Hyatt Regency Savannah – $292/night
Riverfront location, family-friendly amenities, earn World of Hyatt points.

Savannah Gift Ideas

Wrap these with tags like “Open when we arrive in Savannah”:

Day 1 Budget Snapshot

CategoryCostNotes
Hotel$82Budget option outside district (Best Western downtown = $142)
Food$70Fast food before arrival + pralines on River Street
Activities$0Free River Street walk (ghost tour ~$17/person optional)
DAILY TOTAL$152Add ghost tour if desired

Day 2: Savannah Georgia – Full Day in Historic District (Budget: $152)

Savannah Georgia stone streets with people shopping on the street

Savannah feels different the moment you arrive. Cobblestone streets, Spanish moss dripping from massive oaks, historic squares around every corner—this city moves slower, and that’s the point. Take your time wandering. You’ll stumble onto street musicians, hidden gardens, and stories around every turn. This is the South at its most charming.

Day 2 Plan: Explore Savannah

You have a full day with no driving – make the most of it. Start early to beat the heat (it gets warm by afternoon even in February), wander the squares at your own pace, and soak in that slow Southern vibe. You have a full day with no driving – make the most of it. Start early to beat the heat (it gets warm by afternoon even in February), hit the major sights, then slow down for a nice dinner tonight.

Suggested flow:

Must-Do Activities

🪣 Bucket-List Stops

Forsyth Park & Fountain – Free
The iconic white fountain you’ve seen in every Savannah photo. Visit in the morning for shade and better light. The park is huge – bring a picnic or just walk the paths under the live oaks.

River Street – Free
Cobblestone waterfront street with shops, restaurants, and river views. Watch cargo ships pass by, grab pralines, listen to street musicians. Gets crowded but that’s part of the charm.

Historic District Squares – Free
22 squares total, each with its own personality. Don’t try to see them all – just wander and discover. Our favorites: Chippewa Square (Forrest Gump bench scene), Madison Square (moss-covered oaks), Monterey Square (Mercer House).

Quirky & Unique Stops

These are Atlas Obscura picks – weird, interesting, and very Savannah:

Graveface Museum – $24.99/person
True crime and oddities museum with murder memorabilia, serial killer artifacts, and macabre collectibles. Not for kids. For true crime fans only.

American Prohibition Museum – $16.10/adult
Interactive 1920s bootlegging museum with a speakeasy bar experience at the end. Fun for history buffs and anyone who likes period pieces.

Rousakis Plaza Echo Square – Free
Stand in the center and hear your voice echo back – simple acoustic trick, quick photo op. Right on River Street.

Abe’s On Lincoln – Free to enter (restaurant)
Draw on a dollar bill, sign it, and tack it to the walls covered in customer art from visitors. Grab lunch while you’re there. It’s a fun tradition.

💡 Leave Your Mark: This is one of those places where you can actually leave something behind! Sign a dollar bill and add it to the walls. (Love this idea? We have a whole “Leave Your Mark” category on our site with spots across the US where you can do the same!)

Free Activities

City Market – Free
Outdoor market with local art stalls, street musicians, and cafes. Good for people-watching and browsing. Grab a coffee and sit.

Broughton Street – Free
Main shopping street with a mix of local boutiques and familiar brands. Good for window shopping and air conditioning breaks.

Colonial Park Cemetery – Free
Historic graveyard from the 1750s. Peaceful walk among old headstones, Spanish moss, and Georgia history. Some graves date back to the Revolutionary War.

Tybee Island Beach – Free (optional, 25-35 min east)
Early bird? Catch sunrise at the pier while the teenagers sleep in. Or hit it this afternoon as you head toward St. Augustine tomorrow. Either way, don’t miss being this close to the ocean.

Paid Activities

Savannah Ghost Tour – Starting at $17/person (10% off with code RTOWL)
Tours run nightly, rain or shine. Pick your vibe: classic ghost walk, pub crawl (21+), Bonaventure Cemetery tour, Black History tour, or foodie tour. Arrive 10-15 minutes early and wear comfy shoes.

Hop-On Hop-Off Trolley Pass – $40/person
Unlimited rides for the day with stops at all major Historic District attractions. Great way to cover ground without walking miles in the heat. The guides share history and stories as you ride. This is the Historic Tours of America trolley – gift cards available!

Wormsloe Historic Site – $5.75 under 18, $12 adults
Drive through the famous 1.5-mile oak-lined avenue (one of the most photographed spots in Georgia), explore colonial estate ruins, and learn about early Savannah history. About 20 min from downtown. Worth it if you have extra time and love photography.

Where to Eat in Savannah

Breakfast:

Lunch:

  • Mrs. Wilkes House – All-you-can-eat Southern family-style at shared tables (fried chicken, mac & cheese, collards – the works). Cash only, closes at 2pm, expect a line.
  • Best lunch option: Pack a picnic for Forsyth Park. You’ll sit under 300-year-old oak trees dripping with Spanish moss – if someone could charge for this atmosphere, they would. But it’s free. Grab sandwiches from a local deli or grocery store, spread out under the shade, and enjoy one of the most beautiful lunch spots in America. This beats overpriced tourist restaurants every single time.

Dinner:

Sweet Stops:

💵 Budget tip: Food in Savannah adds up fast in the Historic District. If you’re watching your wallet, eat your main meals outside downtown or grab something quick. Then treat yourself to ONE special thing—pralines, ice cream, or a nice dinner—so you still get the Savannah experience without breaking the bank.

Savannah Gift Ideas (Days 1 & 2)

(These work for either day since you’re here both nights – if you already wrapped these for Day 1, skip this section!)

Where to Stay Tonight

Continue your second night at the same hotel you booked for Days 1 & 2. Tomorrow morning you’ll check out and drive to St. Augustine (2.5-3 hours).

Day 2 Budget Snapshot

CategoryCostNotes
Hotel$82Second night, same hotel
Food$70Mrs. Wilkes lunch + nice dinner tonight
Activities$0Free walking/exploring (trolley $40/person optional)
DAILY TOTAL$152Add trolley or ghost tour if desired

Day 3: St. Augustine Florida – Historic District & Where to Stay (Budget: $138)

Old Jail

Drive: Savannah → St. Augustine (2.5-3 hours)

Why you’ll love it: America’s OLDEST city is calling! Walk cobblestone streets where Spanish settlers built a fortress 450 years ago. Climb a lighthouse for killer ocean views. Stroll a car-free street packed with shops, street musicians, and history on every corner. Here’s the best part: you can explore SO MUCH for free. The trolley? Absolutely worth it—it unlocks even more free spots AND gets you to all the paid highlights without the parking hassle. This city delivers big on the “wow” factor without emptying your wallet.

Optional Stops Between Savannah & St. Augustine

These are slightly off the main route but worth the detour if you have time and energy:

Smallest Church in America – Free
Tiny roadside chapel fits about 12 people max – quick photo op and quirky bragging rights. (Atlas Obscura pick)

Driftwood Beach (Jekyll Island) – Free
Hauntingly beautiful beach covered in sun-bleached driftwood trees – feels like another world, incredible photos. About 30-45 min detour off route.

NaNa Dune – Free
Tallest sand dune in Florida with boardwalk access and ocean views – short climb, big reward. (Atlas Obscura pick)

The Catty Shack Ranch Wildlife Sanctuary – $15/adult
Rescued big cats (tigers, lions, leopards) in naturalistic habitats – feeding tours available, great for animal lovers.

💡 Timing tip: These stops can add 1-2 hours to your drive. Skip them if you want more time in St. Augustine, or hit 1-2 if you’re energized and want to break up the drive.

Day 3 Plan: Explore America’s Oldest City

Arrival: You’ll arrive late morning/early afternoon with a full afternoon to explore.

Game plan:

  • Park once (either at trolley stop or near Castillo fort)
  • Walk St. George Street (car-free, easy to navigate)
  • Decide: trolley tour for convenience OR explore on foot
  • Hit the fort and lighthouse if you’re into those
  • Evening drive to Daytona Beach (1 hour south)

💡 Parking strategy: St. Augustine parking fills up fast and costs $1.50-2/hour at meters. If you’re doing the trolley tour, park at their lot and use the trolley to get everywhere. If you’re walking, park near the fort (pay once) and explore from there.

Must-Do Activities in St. Augustine

🪣 Bucket-List Stops

Castillo de San Marcos – Free to walk around outside, $15/adult to enter (OR use America the Beautiful annual pass)
Historic Spanish fortress on the bayfront with walls you can climb, cannons, and harbor views. The oldest masonry fort in the continental US (built 1672-1695). If you have the America the Beautiful pass (listed in gift section), entry is free.

St. George Street – Free
Car-free cobblestone street lined with shops, restaurants, street performers – the heart of the old city. You could spend hours just wandering and people-watching.

St. Augustine Lighthouse & Maritime Museum – $17.95/adult
Climb 219 steps for panoramic ocean and city views, plus maritime history exhibits. Worth it if you’re not scared of heights and want the photo op from the top.

Paid Activities

Old Town Trolley Tour – Starting at $35.14/person
Hop-on hop-off all day with stops at major attractions. Great way to cover ground without parking hassles, plus the guides share history and stories. Takes you to both free spots and paid attractions – highly recommended if you want to maximize your day without the stress of driving around looking for parking.

Ripley’s Believe It or Not! – $23.99/adult
Oddities museum with shrunken heads, bizarre artifacts, and interactive exhibits. Right on St. George Street – easy to pop in if it’s your thing.

St. Augustine Ghost Tours – Starting at ~$25/person
One of America’s most haunted cities comes alive after dark. Choose from walking tours, pub crawls (21+), or tours of the Old Jail. Use code RTOWL for 10% off at checkout.

St. Augustine Alligator Farm – $35.99/adult
See hundreds of alligators plus exotic birds, lemurs, and reptiles. Add-ons: zipline over gator pit ($59.99), sloth encounter ($25), or hold a baby gator for photos ($10).

Whetstone Chocolate Factory Tour – $4/person
Short, sweet (literally), and a fun pit stop. Quick tour of how chocolate is made plus samples – perfect low-cost gift or treat.

Free Activities

Honestly? You could spend the entire day just wandering St. George Street, peeking into shops, watching street performers, and soaking in the old-world vibe without spending a dime. But here are a few more free highlights:

St. Photios Greek Orthodox National Shrine – Free
Beautiful Byzantine chapel and museum about the first Greek colony in America, right off St. George Street.

Bridge of Lions – Free
Iconic bridge with lion statues – great photo spot overlooking Matanzas Bay.

Anastasia State Park Beach – Free (or $8 parking)
Just a few minutes from downtown, beautiful beach for a sunset walk.

Bayfront/Matanzas Bay Walk – Free
Stroll along the water with fortress views.

Where to Stay Tonight: Daytona Beach (3 Nights)

After exploring St. Augustine, drive about 1 hour south to Daytona Beach. You’ll stay here for 3 nights (Days 3, 4, and 5) before heading to Orlando area.

📅 Book 3 nights in Daytona Beach – you won’t have to pack up again until Day 6.

February means affordable oceanfront rooms – book early for the best selection. Is the ocean warm? No. Will your teenagers still swim anyway? Absolutely. (Mine do.) The water’s in the low 60s – chilly but refreshing on sunny days. Worst case, the hotel pool is heated.

All prices include taxes and are based on February 2026 bookings.

Budget Options (Under $130/night)

Extended Stay – Ormond Beach – $68/night
Suite with kitchenette, about 10 min north of Daytona. Solid budget pick.

Beach House Inn – $76/night 👈 Best value for oceanfront
Right on the beach, basic but solid reviews, unbeatable price for ocean access.

Oceanfront Views

Oceanfront Inn and Suites – Ormond – $123/night
Ormond Beach (just north of Daytona), oceanfront rooms with balconies.

Holiday Inn & Suites Daytona Beach – $134/night
Oceanfront, reliable Holiday Inn brand, walkable to boardwalk.

Fountain Beach Resort Daytona Beach – $162/night
Oceanfront with pool and beach access.

Hyatt Place Daytona Beach – Oceanfront – $166/night
Oceanfront Hyatt, earn World of Hyatt points, modern rooms.

St. Augustine Gift Ideas

Day 3 Budget Snapshot

CategoryCostNotes
Hotel$68First night in Daytona Beach (Beach House Inn = $76)
Food$70Lunch in St. Augustine, dinner on the road or in Daytona
Parking$0Street parking in St. Augustine ~$10–15 if needed
Activities$0Free walking St. George Street (fort $15, trolley $35 optional)
DAILY TOTAL$138Add paid activities if desired

Day 4: Daytona Beach Florida – Drive on the Sand & Beach Day (Budget: $138)

daytona international speedway

This is THE beach where you can literally drive your car on the sand – how cool is that? Daytona delivers that classic Florida beach town energy: a historic boardwalk, an iconic lighthouse you can climb, and if you’re into racing, the Speedway is right here. Spend the day as low-key or as packed as you want. Walk for miles on firm sand, grab pier photos, hunt for sharks’ teeth, or just post up with a cooler and watch the waves. This is your chill beach day with options.

Day 4 Plan: Beach Day

You’re already here – no checkout, no packing. Sleep in, hit the beach, explore at your own pace.

Suggested flow:

  • Morning: Drive on Daytona Beach (pay the beach access fee, park right on the sand)
  • Late morning/lunch: Boardwalk area, walk the pier
  • Afternoon: Ponce Inlet Lighthouse OR Speedway tour OR more beach time
  • Evening: Sunset beach walk or boardwalk dinner

💡 Flexibility tip: If yesterday was a long day in St. Augustine, make today super chill. If you’re energized, add the Speedway or lighthouse.

Must-Do Activities

🪣 Bucket-List Stops

Drive on Daytona Beach – ~$20/vehicle beach access fee
One of the few beaches in America where you can drive right on the sand. Park your car, pop the trunk, set up chairs. Follow posted signs and fee stations. The sand is firm enough to drive on safely – just watch for soft spots near the water.

Daytona Beach Bandshell & Boardwalk – Free
Iconic 1930s amphitheater, classic pier, beach views, and old-school boardwalk energy. Walk the pier for ocean views and that classic Florida beach town vibe.

Ponce Inlet Lighthouse – $6.95/adult
Climb Florida’s tallest lighthouse (203 steps) for panoramic ocean views and explore the maritime museum. About 15 min south of main Daytona Beach.

Daytona International Speedway – Free to browse store, paid experiences $25-$500+
Ever wondered what 180mph feels like? You can DRIVE a NASCAR here (pricey but unforgettable) or ride shotgun for less. The 60-minute guided tour (included FREE with Go City Pass) takes you to the start/finish line, garages, victory lane, and includes admission to the Motorsports Hall of Fame of America. Without the pass, the tram tour is around $25-30. There’s probably someone in your crew who’d lose their mind over this.

Free Activities

Long beach walk – Free
Firm sand makes it perfect for walking miles – great for early birds or sunrise strolls. You can walk for literally miles and the sand stays firm.

Dunlawton Sugar Mill Gardens – Free
Peaceful botanical gardens with historic sugar mill ruins, shaded paths, and zero crowds. Nice escape from the beach scene.

Ormond Loop Scenic Trail – Free
Quick nature escape with Florida scrub habitat and scenic pull-offs. Good for a different vibe if you’re beached-out.

Bongoland Ruins – Free
Creepy, overgrown remains of a 1940s roadside zoo – perfect for photos and a weird story. (Atlas Obscura pick)

Daytona Beach Gift Ideas

Where to Stay Tonight

Stay in the same hotel as last night (Day 3). You’ve got one more night here before heading to Orlando area tomorrow.

Day 4 Budget Snapshot

CategoryCostNotes
Hotel$68Second night, same hotel
Food$70Beach picnic or boardwalk dining
Beach Access$0–$20~$20 if you drive on the beach
Activities$0Free beach day (lighthouse $7, Speedway tour $25 optional)
DAILY TOTAL$138Add beach driving fee or paid activities if desired

📅 Event Alert (February/March): If you’re visiting during Daytona 500 race week (mid-February) or Bike Week (early March), expect major crowds, higher hotel rates, and heavy traffic. Book hotels months ahead or consider staying north in Ormond Beach or south in New Smyrna for easier access. The energy is electric but plan accordingly!

Day 5: Orlando Area Florida – Theme Parks or Free Activities (Budget: $138)

Topiary-style Mickey Mouse statue pouring water into a large pot fountain at Disney Springs

Drive: Daytona Beach → Orlando/Kissimmee (~1 hour)

Here’s the deal: Orlando is MASSIVE. You have one day. You have three options – pick ONE based on your budget and what your family wants.

Day 5 Plan: Choose Your Adventure

Option 1: Theme Park Day (Big Splurge)
Each park is massive and can easily fill a full day. Most people stick to one park per day, but if you want to park-hop, Disney and Universal both offer multi-park tickets.

Option 2: Go City Pass Day (Best Value If You Have the Pass)
Hit multiple smaller attractions, get free meals at shows, and maximize that pass you already bought.

Option 3: Free Orlando Day (Save Your Money)
Disney Springs, Old Town Kissimmee, free exploring – still fun, zero cost.

Option 4: Skip Orlando, Stay at the Beach
You drove all this way to Florida. The ocean is literally right there. Spend the day at the beach, sleep in, read a book, let the teenagers boogie board. Not every day needs an itinerary. This is vacation.

💡 Drive back to Daytona Beach tonight for your third night in the same hotel. Tomorrow you’ll check out and head to Cocoa Beach.

Option 1: Theme Park Day

Pick a park:

Universal Studios – $119/adult
Movies, rides, Wizarding World of Harry Potter (Diagon Alley). Best for older kids and teens who love thrill rides and Harry Potter.

Magic Kingdom – $119/adult
Classic Disney with Cinderella Castle, Space Mountain, rides for all ages. Best for families with younger kids or Disney fans.

EPCOT – $119/adult
World Showcase, unique pavilions, food and culture. Best for families who want something different than typical theme park.

💰 Plan ahead: Theme park tickets run $119/person ($476 for family of 4). Add parking and food, you’re looking at more. Worth every penny if this is what your family wants – just factor it into your overall trip budget so there are no surprises.

Option 2: Go City Pass Day (If You Have the Pass)

If you bought the Go City Pass, this is where it shines. You can hit multiple attractions in one day, get free meals at shows, and actually use that pass.

Maximize your pass:

  • Start early (9am)
  • Hit 3-5 attractions throughout the day
  • Include at least one show with free meal
  • Use hop-on hop-off transportation if available

Top picks from the pass:

💡 Pro tip: Our Orlando Attraction Pass Planning Guide includes a timed itinerary showing how to hit 8 attractions in one day. Spoiler: Start at 9am, end around 8pm, plan your meals around the free show dinners.

Option 3: Free Orlando Day

No theme park tickets? No problem. Orlando has some genuinely cool free (and cheap) experiences that don’t feel like you’re missing out.

Disney Springs – Free
Massive outdoor shopping and dining complex with that Disney magic – no ticket required. Watch street performers, browse the LEGO store, people-watch, grab lunch. You get the Disney atmosphere without the $119 entry fee.

Old Town Kissimmee – Free
Vintage Florida vibes with classic car shows on weekends (Fridays and Saturdays). Browse the quirky shops (there’s a hippie store with wild tie-dye and incense that’s fun to explore), try alligator bites at one of the food stands (tastes like chicken, but chewier – it’s a Florida rite of passage), and soak in that retro 1950s charm. It’s kitschy on purpose and honestly pretty fun.

World’s Largest McDonald’s – Just pay for food
Yes, really. This 3-story McDonald’s serves pizza, pasta, and has a massive arcade. It’s ridiculous and your teenagers (and twenty-somethings) will love it. It’s an experience, not just fast food.

World of Food Trucks – World of Food Trucks – 80 FOOD TRUCKS in one spot – cuisines from around the world, all easy to access. Everyone gets exactly what they want (tacos for one kid, Greek for another, BBQ for dad, Asian fusion for mom). Way cheaper than restaurants, zero compromise, and honestly just fun to walk around. This is what makes Florida road trips memorable. Don’t skip this.

ICON Park area – Free to walk
Home of the Orlando Eye (costs money to ride), but the area itself is free to explore with restaurants, shops, and atmosphere.

💡 This is a great day if: Your family prefers quirky exploration over theme park crowds. You’d rather discover the world’s largest Happy Meal box than wait 2 hours for one ride. Free doesn’t mean boring – it means choosing experiences over admission tickets.

Orlando Area Gift Ideas

Theme Park Tickets:

Dining:

Activities Pass:

  • Go City Pass (covered in detail earlier) – $219/person for 2 days, unlocks all the attractions listed in Option 2 above

Where to Stay Tonight

Drive back to Daytona Beach for your third and final night at the same hotel. Tomorrow morning you’ll check out and head to Cocoa Beach.

Day 5 Budget Snapshot

CategoryCostNotes
Hotel$68Third night in Daytona Beach
Food$70Could be $0 if using hotel breakfast + 2 Go City Pass meals
Activities$0Free options OR theme park $476 for family OR included in Go City Pass
DAILY TOTAL$138Add theme park tickets if splurging ($476 for family of 4)

Day 6: Cocoa Beach & Kennedy Space Center – Space Coast (Budget: $199)

Kennedy Space Center in florida christmas time
Photo credit Beth Daniels

Drive: Daytona Beach → Cocoa Beach (~45 minutes south on I-95 or A1A)

Stand where rockets launched to the moon. Watch wildlife in a pristine refuge. Walk a classic beach pier at sunset. This stretch of Florida’s Space Coast packs serious variety into one compact day – from NASA history to untouched beaches to Port Canaveral’s working waterfront. You can go full space nerd at Kennedy Space Center OR skip the ticket price and still have an incredible beach and wildlife day. And if there’s a launch scheduled? You can watch a rocket take off from the beach for free – one of the coolest things you’ll ever see. Either way, you’re getting Florida at its most unique.

Day 6 Plan: Space Coast Adventure

Morning/Afternoon: Kennedy Space Center (plan 4-6 hours minimum – there’s a LOT to see)
Late Afternoon: Cocoa Beach Pier, beach walk, Ron Jon Surf Shop
Optional: Merritt Island Wildlife Refuge or Canaveral National Seashore
Evening: Drive about 2 hours south to West Palm Beach/Fort Lauderdale area for tonight’s hotel

💡 Why drive 2 hours tonight? Hotels along the coast between Cocoa Beach and Miami are $200+/night in February. Driving to the Palm Beach Gardens/Fort Lauderdale area saves you $50-100 AND gets you closer to Miami for tomorrow. It’s a bit of a haul after a full day, but your wallet will thank you.

Must-Do Activities

🪣 Bucket-List Stop

Kennedy Space Center Visitor Complex – ~$75/adult (FREE with Go City Pass)
This is what you came for. See the Space Shuttle Atlantis up close, walk through the Rocket Garden where real rockets tower above you, and take the bus tour to the massive Saturn V center. Plan 4-6 hours minimum – there’s SO much to see and do. If you only do one paid thing in Florida, this is it.

Cocoa Beach Pier – Free
Classic 800-foot pier stretching into the Atlantic. Walk it for ocean views, grab a photo at the iconic sign, watch surfers, or just soak in that old Florida beach town vibe.

Free (or Low-Cost) Activities

Cocoa Beach Sunrise Walk – Free
Wake up early and catch sunrise over the Atlantic – spectacular ocean views and peaceful morning vibes before the crowds arrive.

Ron Jon Surf Shop – Free
Massive, colorful surf shop open 24/7. Free to browse, iconic Cocoa Beach photo op. It’s huge inside – you could spend 30 minutes just looking around.

Merritt Island National Wildlife Refuge – $5/vehicle (free with America the Beautiful pass)
Drive-through wildlife loop – spot gators, birds, and seasonal manatees from your car. No hiking required, just slow driving and wildlife watching.

Canaveral National Seashore – $25/vehicle for 7-day pass (free with America the Beautiful pass)
Pristine, undeveloped beach that feels wild and remote. Worth it if you want that untouched Florida coastline experience.

🚀 Rocket Launch Alert

Launches happen at Cape Canaveral almost WEEKLY – SpaceX alone launches multiple times per month. But here’s the catch: many launches are only added to the schedule a few weeks (or even days) out.

Check the launch schedule about 1-2 weeks before your trip to see if anything’s scheduled for Day 6. If there is, don’t miss it! You can watch for free from Cocoa Beach, Jetty Park, or along the causeways – no Kennedy Space Center ticket needed.

Launch viewing tips:

  • Bring binoculars or a camera with zoom
  • Be ready for weather delays (they’re common)

Even if the launch gets delayed, you’ll still remember standing on the beach with everyone counting down. It’s pretty cool.

Optional Adventure (If You Want to Splurge)

Not everyone needs this, but if you’re looking to splurge on something truly memorable, here’s an option that makes Cocoa Beach special:

Deep-Sea Fishing Charter – Starting at ~$400 for the boat

Port Canaveral is a major fishing hub with options for every budget. Family fun trips start around $400, night shark fishing runs $550, or go all-out with a full-day deep-sea charter ($1,400). It’s a bucket-list experience you’ll talk about for years. We’ve covered all the details in our Deep-Sea Fishing Charter Guide including different trip types, what to expect, what’s included, and how to book.

Where to Stay Tonight: West Palm Beach/Fort Lauderdale Area

After a full day at Cocoa Beach, you’re heading south toward Miami. Here’s the deal: hotels along the coast between Cocoa Beach and Miami are running $200+/night for February. So we’re suggesting you drive about 2 hours tonight to the Palm Beach Gardens/Fort Lauderdale area where you can stay under $185. It saves you $50-100 AND gets you closer to Miami for tomorrow.

All prices include taxes and are based on February 2026 bookings.

Budget-Friendly Options

Hawthorn Extended Stay By Wyndham Ft Lauderdale Cypress Creek – $129/night 👈 Best budget pick
Suites with kitchenettes, solid reviews, gets you in the area without breaking the bank.

The Jaxon – $148/night
Boutique hotel in West Palm Beach, modern vibe, pet-friendly, kitchenettes and outdoor games area.

Best Western Plus Palm Beach Gardens Hotel & Suites – $183/night
Full-service hotel with conference center, free breakfast, reliable brand.

Cocoa Beach Gift Ideas

Day 6 Budget Snapshot

CategoryCostNotes
Hotel$129West Palm Beach/Fort Lauderdale area (Best Western = $183)
Food$70Lunch at Cocoa Beach, dinner on the road or at hotel area
Activities$0Free beach/pier (Kennedy Space Center $75/person optional)
DAILY TOTAL$199Add Kennedy Space Center if not using Go City Pass

Day 7: Miami Florida – South Beach & City Vibes (Budget: $183)

Wynwood Walls

Drive: West Palm Beach/Fort Lauderdale area → Miami (45 min – 1 hour)

Optional scenic route: If you’re near Fort Lauderdale, take Ocean Boulevard (Jimmy Buffett Memorial Highway) for 15-20 minutes instead of the interstate. You’ll drive right along the water with palm trees and beach views – pure Florida postcard vibes. Not necessary, just pretty.

You’ve got a few hours in Miami before heading to Homestead. Here are your two options:

Option 1: South Beach/Downtown Miami – If you want the Instagram version of Miami
This is what you see in movies – pastel Art Deco buildings, Ocean Drive sidewalk cafes, beautiful people, expensive everything. You’ll pay for parking and might circle a bit to find a spot, but it’s doable. Honestly? It’s more about being seen than seeing anything special. If your teenagers want that classic Miami photo op, go for it.

Option 2: Wynwood & Little Havana – If you want actual Miami culture (our pick)
Wynwood Walls has incredible street art (free), Little Havana has authentic Cuban food and culture (affordable), and parking is plentiful and easy in both areas. This feels like a real neighborhood, not a tourist set. You’ll eat better, spend less, and actually experience something unique. Way more interesting than South Beach, and your teenagers will get better photos from the murals anyway.

Real talk: If you’re not super into Miami, skip South Beach entirely. Go straight to Wynwood for the art, grab Cuban food in Little Havana, and save your energy for the Keys tomorrow. You won’t miss anything except overpriced drinks and paid parking.

Day 7 Plan: Choose Your Miami Area

Morning/Early Afternoon: Arrive in Miami, pick your area (South Beach OR Wynwood/Little Havana)
Afternoon: Explore, eat, soak it in
Evening: Drive 45-60 minutes south to Homestead/Florida City (your launchpad for the Keys tomorrow)

💡 Go City Pass strategy: Already have the pass from Orlando? Your 2-day pass covers Miami too, but think strategically about your second day. Miami has a TON of amazing FREE stuff (Wynwood Walls, Little Havana, South Beach), so you might not need the pass here. Consider:

Use your 2nd pass day in Miami if:

Save your 2nd pass day for elsewhere if:

  • You’re happy with Miami’s free attractions
  • You’d rather use it in Tampa/Clearwater area (also covered)
  • You want maximum value from paid activities elsewhere

Must-Do Activities

🪣 Bucket-List Stops

South Beach & Art Deco District – Free (paid parking)
Walk Ocean Drive, see the colorful 1930s buildings, people-watch at sidewalk cafes, hit the beach. This is the Miami everyone pictures – pastel buildings, palm trees, beautiful people.

Wynwood Walls – Free (easy parking)
Outdoor street art museum with massive murals – constantly changing, always Instagram-worthy. Artists from around the world paint these walls. Just walk around and take it all in.

Little Havana (Calle Ocho) – Free (easy parking)
Cuban culture, ventanita coffee (walk-up window coffee – get one, it’s strong and delicious), watch locals play dominoes at Maximo Gomez Park, grab authentic Cuban food. This is real Miami, not tourist Miami.

Free Activities

Miami Trolleys – Free citywide trolley system
Multiple routes covering different neighborhoods. Download the Miami Trolley Tracker app to see real-time locations – easy way to get around without parking hassles. Way better than circling for parking.

South Pointe Park – Free
Park at the southern tip of South Beach with great skyline and ocean views. Less crowded than the main beach.

Bayside Marketplace – Free
Waterfront shopping/dining complex with street performers and bay views. Good for a quick walk and air conditioning break.

Paid Activities

Zoo Miami – $24.95/adult (included in Go City Miami pass)
Largest zoo in Florida with over 3,000 animals. Good option if weather’s bad or you need a break from walking cities.

Water Taxi – ~$30/person all-day pass
Your teens will think this is the coolest thing ever. It’s literally a boat that works like a bus, hopping between South Beach, Bayside, and other waterfront stops. Way more fun than an Uber, and you’re seeing Miami from the water while getting around.

Big Bus Hop-On Hop-Off – Included in Go City Pass Miami and Orlando
All-day pass with stops at major attractions. Saves walking and parking if you want to hit multiple areas.

Where to Eat in Miami

Cuban Food in Little Havana – Budget-friendly
Authentic Cuban sandwiches, croquetas, pastelitos, and ventanita coffee (coffee from a walk-up window) – this IS the experience. Cheap, delicious, and you’ll be full.

Bayside Marketplace – Mid-range
Casual waterfront dining with lots of options – tacos, bowls, seafood.

Hard Rock Cafe Miami – Splurge option
The iconic giant guitar building with rock memorabilia covering every wall and a gift shop. Good rain-day option – free to walk around and look even if you don’t eat.

Alternative Adventure: Skip the Keys & Cruise Instead

Not everyone needs to drive to Key West – and if you’re looking to maximize relaxation while minimizing driving, here’s a completely different option:

2-4 Night Cruise from Miami – Starting at ~$199/person for 4 nights (base fare)

Important: I couldn’t give you an exact out-the-door price because cruise lines require your age, email, and location before showing final costs. Prices vary based on whether you’ve sailed before, where you live, and current promotions.

Miami is one of the world’s busiest cruise ports with sailings to the Bahamas, Caribbean, and Key West multiple times per day. For around $199/person base fare (taxes, port fees, and gratuities are extra), you get 4 days of all-you-can-eat meals, entertainment, pools, and island stops. When you factor in hotels + gas + food for Days 8-10, a cruise could actually be cheaper – plus way less driving.

⚠️ Passport note: Technically you don’t need a passport for closed-loop cruises (leaving from and returning to Miami), but you WILL need one if you want to actually get off the ship at island stops. You can stay on the boat without a passport. Apply for passports early – they can take 6-12 weeks.

Where to Stay Tonight: Homestead/Florida City

After your Miami day, drive 45-60 minutes south to Homestead/Florida City. This is your strategic overnight stop – not a tourist destination, but that’s the point. You’re positioning yourself for tomorrow’s Keys adventure. There are plenty of restaurants if you’re hungry, and the hotels are clean and affordable. Finish your Miami exploration first, then head here to rest up for the big drive tomorrow.

All prices include taxes and are based on February 2026 bookings.

Budget Options

Fairway Inn Florida City Homestead Everglades – $113/night 👈 Best budget pick
Basic budget option near the highway, good for one night.

Super 8 by Wyndham Florida City/Gateway to Keys/Everglades – $117/night
Budget-friendly, right off the main route, clean enough for an overnight.

Garden Inn Homestead – $123/night
Step up from the cheapest options, pool included.

Mid-Range Chain Hotels

Holiday Inn Express & Suites Florida City – $188/night
Gateway to the Keys location, free breakfast, clean and safe.

Tru By Hilton Florida City – $224/night
Modern budget brand, clean design, good for quick overnight.

Hampton Inn & Suites Miami-South/Homestead – $291/night
Reliable Hampton quality, free hot breakfast, earn Hilton Honors points.

Hilton Garden Inn Homestead – $256/night
Pool, fitness center, earn Hilton Honors points.

Unique Option

The Hotel Redland – $156/night
Historic 1904 hotel, fully refurbished, boutique vibe, one block off main highway. If you want something different from chain hotels.

Miami Gift Ideas

Day 7 Budget Snapshot

CategoryCostNotes
Hotel$113West Palm Beach/Fort Lauderdale area (Best Western = $183)
Food$70Lunch at Cocoa Beach, dinner on the road or at hotel area
Activities$0Free beach/pier (Kennedy Space Center $75/person optional)
DAILY TOTAL$183Add Kennedy Space Center if not using Go City Pass

Day 8: Florida Keys Day Trip – Overseas Highway to Key West (Budget: $183)

Key west drive road lined with palm trees

Drive: Homestead → Key West is ~160 miles (3 hours one way via Overseas Highway US-1)

Here’s the deal: The Florida Keys are AMAZING. The atmosphere is unlike anywhere else in Florida – turquoise water, island vibes, that laid-back energy you can’t fake. The drive down the Overseas Highway with bridges stretching over open ocean? Unforgettable. The vibe of walking around Key West at sunset with street performers and chickens roaming Duval Street? You’ll be talking about it for years.

But here’s the strategy most guides won’t tell you: you can capture the absolute best of the Keys in ONE incredible day and leave dying to come back – which is way better than spending three days (and $300+/night hotels) doing the same activities and thinking “okay, what’s next?” The beaches aren’t continuous like some coastal drives (rocky shores in spots, not a “park anywhere and swim” situation), but that’s not why you came. You came for the VIBE. And one perfect day gives you all of that magic without the massive price tag.

The strategy: Decide this morning whether you’re staying overnight in Key West or driving back to Homestead (see hotel options below – you’ll need to plan ahead). Either way, drive down with strategic stops, soak in Key West at sunset with the street performers, and leave while you’re still obsessed with the place.

🦎 Wait, Is That an Iguana?! (Welcome to the Keys Wildlife)

Before you hit the road, fair warning: you’re going to see iguanas. Like, BIG iguanas. Just chilling on the side of the road, sunbathing on rocks, crossing the highway like they own the place. If you’ve never seen one in the wild before, it’s absolutely mind-blowing the first time. They’re everywhere in the Keys – green iguanas, some of them 4-5 feet long – and yes, they’re invasive, but they’re also just… there. Part of the scenery now. Don’t freak out, don’t try to touch them (they’re wild animals), just enjoy the moment and snap a photo if you can do it safely.

And in Key West? Get ready for the chickens. Roaming freely. Everywhere. They’re protected, they’re loud, and they strut around Duval Street like tourists. It’s weird, it’s hilarious, and it’s 100% Key West. The teenagers will get a kick out of it.

So yeah – iguanas on the highway, chickens in the streets, pelicans at the marina. The Keys are wild in more ways than one. 🐔🦎

Day 8 Plan: Keys Adventure

Timeline:

  • 9-10am: Depart Homestead (optional Robert Is Here fruit stand)
  • 10am-2pm: Drive down with strategic stops (Betsy the Lobster, Robbie’s Marina, Seven Mile Bridge)
  • 2-3pm: Arrive Key West
  • 3-7pm: Explore Key West (Southernmost Point, Duval Street, walk to sunset at Mallory Square)
  • 7-8pm: Sunset celebration at Mallory Square
  • Evening: stay overnight in Key West OR drive back to Homestead

💡 Important: Stop at the attractions on your way DOWN. Many close early, and you’ll be driving back at night when everything’s closed. Don’t skip them thinking “we’ll stop on the way back.”

Optional Quick Start: Robert Is Here Fruit Stand

Hours: Opens at 9am daily
Time needed: 15-20 minutes

If you’re a “try weird fruit and bring home edible souvenirs” kind of family, Robert Is Here is worth the stop. This iconic roadside fruit stand (around since 1959) sells tropical fruit you’ve probably never heard of – mamey, sapodilla, sugar apple, carambola, dragon fruit, lychee – plus the best Key lime milkshakes in South Florida. There’s a small petting zoo out back (goats, emus, tortoises), and the whole vibe is pure old-Florida charm.

Skip if: You’re not into quirky roadside stops, you’re running late, or you just want to get to the gators and ocean ASAP.

Must-Stop Highlights on the Drive Down

(Listed north to south – you’ll hit these in order)

Betsy the Lobster at Rain Barrel Village (Mile Marker 86.7, Islamorada) – Free
Giant 40-foot lobster statue for epic photos PLUS an artisan village with local art, jewelry, and gifts. The Lobster Shack has lunch, and there’s even a bar. Fair warning: there are TONS of roadside attractions along US-1. This one’s worth the stop.

Robbie’s Marina (Islamorada, MM 77.5) – $4 to feed tarpon
Feed massive tarpon from the dock – they’re HUGE and will splash you – browse the outdoor market, grab lunch from the food stalls. This is THE iconic Keys experience everyone talks about.

Bonus: The Hungry Tarpon restaurant has a bar lined with dollar bills from visitors who signed their name and left their mark. Grab lunch, sign a dollar, and add yours to the walls – it’s a fun tradition and the waterfront views are unbeatable.

💡 Leave Your Mark: This is one of those places where you can actually leave something behind! Sign a dollar bill at the Hungry Tarpon bar and tack it up with all the others. (Love this idea? We have a whole “Leave Your Mark” category on our site with spots across the US where you can do the same – from love lock bridges to wall signatures to painted rocks!)

Seven Mile Bridge Viewpoint – Free
Pull off at the Old Seven Mile Bridge access (Marathon area) for photos of the famous bridge stretching across bright blue water – this is your postcard shot.

Key West – Southernmost Point & Sunset Vibes

Arrival time: Aim for mid-afternoon (2-3pm) to have time for everything.

🚗 Parking strategy: Park as close to Mallory Square as you can find (there are paid lots and street parking nearby). Why? Because all the main sights are walkable from here, and when the sunset show ends, you’ll be RIGHT next to your car – no trudging back through dark streets when everyone’s tired. Drop a pin on your phone or use an app like “Find My Parked Car” so you can easily navigate back. (Trust me, Key West’s streets all look the same after dark!)

The walking route: From Mallory Square, stroll down Whitehead Street toward the Southernmost Point (~1.5 miles). Grab your photo at Mile Marker 0 along the way (corner of Fleming Street), then keep going south. The walk itself is half the fun – you’ll pass colorful conch houses, quirky shops, street art, hidden gardens, and plenty of photo ops. It’s sightseeing, not just walking. Grab the Southernmost Point photo, wander back up through Duval Street popping into whatever catches your eye, then loop back to Mallory Square for sunset. You’re exploring the whole time – Key West is made for wandering.

Key West Bucket-List Activities

Southernmost Point Marker – Free
The iconic red, black, and yellow buoy marking 90 miles to Cuba. Prepare for a line of people waiting for photos – it’s THE Key West photo op.

Mile Marker 0 – Free
Just around the corner at Whitehead & Fleming Streets – the official end of US-1. Quick photo op while you’re in the area.

Duval Street – Free
The main drag packed with shops, bars, restaurants, street performers. This IS Key West – just walk it and soak it in.

Mallory Square Sunset Celebration – Free
Nightly street performer show as the sun sets over the Gulf – jugglers, musicians, artists. This is when Key West comes alive. Stay for this.

Where to Eat in Key West (Budget Reality Check)

Food in Key West can be expensive – waterfront restaurants, tourist pricing, and island logistics all add up. Here’s your strategy:

Budget-friendly options:

  • Cookout at Fort Zachary Taylor State Park – The park has charcoal grills at the beach (bring your own charcoal), or bring your portable gas grill from the gift list. Grab hot dogs, burgers, charcoal, and supplies in Homestead this morning, then grill lunch at the beach with ocean views.
  • Subway – There’s a Subway on Duval Street if you need a quick, cheap meal.
  • Fast food chains – McDonald’s, Wendy’s exist in Key West (not visible from main tourist areas). Use Google Maps to find them.

Splurge:

  • Waterfront dining on Duval Street – Beautiful views with a great atmosphere

💡 Budget reality: Our baseline $70/day budget assumes packed lunch and fast food. Waterfront dining in Key West runs $25-40+/person – totally worth it if you want to splurge on atmosphere and views, just plan ahead so it doesn’t surprise you.

Paid Activities

Fort Zachary Taylor Historic State Park – $6/vehicle
Best snorkeling right from the beach in Key West. Pay once to enter the park (covers parking), bring your own snorkel gear from the pre-trip packing list, and you’re set. The water is clear, you’ll see tropical fish, parrot fish, coral – it’s the real deal. Rocky beach though (it’s limestone), so water shoes are recommended. Park is open 8am-sundown, fort tours available until 5pm.

Ernest Hemingway Home & Museum – ~$17/adult, kids free
If you have Hemingway fans in the group, this is cool. Six-toed cats roam the property (descendants of Hemingway’s pets). Skip if you’re tight on time.

Conch Tour Train or Old Town Trolley – ~$40/person
Narrated 90-minute tour of Key West history and sights. Good if you want the full story without walking miles. Not essential if you’re comfortable exploring on your own.

Florida Keys Gift Ideas

  • Key West trolley tour tickets – For the history buffs who want the narrated tour (~$40/person for hop-on/hop-off all day)
  • Mallory Square street performer tips – Tuck $20-40 in smaller bills ($1s and $5s) in an envelope labeled “Sunset Show Tips” so the kids can tip performers they loved. The performers work for tips, and the teens will feel great handing out dollars to jugglers and musicians.

Tonight – Two Options

Option A: Stay in Key West (memorable, $$$)

Best Western Hibiscus Motel – $376/night
Right in Key West (one block from Duval Street), heated pool, free breakfast, free parking, quiet neighborhood. Most convenient option but highest price.

Sugar Loaf Lodge – $303/night
15-17 miles from Key West (20-25 min drive). Waterfront resort on Sugarloaf Key with pool, water views, tiki bar area. Retro Keys vibe, much cheaper than staying in Key West proper.

Matecumbe Resort – $232/night
In Islamorada, 70 miles from Key West (1.5 hour drive north). Beachfront resort with pool, full kitchens, private beach. Cheapest option but you’re WAY up in the middle Keys – basically backtracking halfway to where you started.

Pros: Sunrise beach walk at Fort Zachary, “we stayed in Key West!” bragging rights
Cons: $300+/night hotels, parking fees, resort fees, not much to do after sunset besides expensive bars

Best for: Families who want the “we stayed in Key West!” experience

Option B: Return to Homestead/Florida City (budget-friendly)

Drive ~2.5 hours back to the same hotel as last night.

Pros: Way cheaper hotels, easy parking, same hotel as last night (you know where everything is)

Cons: Extra 2.5 hours of driving after a full day

Reality check: It’s nighttime highway driving when everyone’s already in “chill mode” from the day. We’ve done this route multiple times and it’s way more doable than it sounds. The 2.5-hour drive back becomes your wind-down time – windows down, music on, everyone decompressing from the day. You’re saving $100+ on a hotel room (plus parking fees, resort fees, all that Key West upcharge nonsense), and honestly? You’re not missing anything by leaving. The magic happens at sunset. After that, it’s just expensive drinks and late-night bar crowds.

Best for: Budget-conscious families who’d rather save $100+ for tomorrow’s activities

Day 8 Budget Snapshot

CategoryCostNotes
Hotel$113Return to Homestead (or $232–376 if staying in Keys area)
Food$70pack snacks or budget for splurge
Activities$0Free exploring (Fort Zachary $6, tarpon feeding $4 optional)
DAILY TOTAL$183overnight in Keys if staying ($232–376)

Day 9: Everglades & Naples – Gators, Airboats & West Coast (Budget: $258)

alligator going through the swamp seen on an airboat tour

Route: Homestead → Everglades National Park (US-41 Tamiami Trail) → Marco Island Tigertail Beach → Naples Tin City → Venice/Caspersen Beach area

Total drive time: ~4 hours (not counting stops) | Activities: Airboat tour, gator spotting, beach shelling, waterfront shopping

Today you’re crossing Florida from the Atlantic to the Gulf Coast, and the drive itself is half the adventure. The Tamiami Trail (US-41) cuts straight through the Everglades where you’ll see more alligators than you can count – just pull over at the canal viewpoints and watch them sunbathe. Add an airboat tour for the full Everglades experience, hit Marco Island for incredible shelling (if you have time), browse Naples waterfront shops, then position yourself near Venice for tomorrow’s shark tooth hunting.

Day 9 Plan: Cross to the West Coast

Timeline:

  • 8-9am: Depart Homestead (optional: Robert Is Here fruit stand if you skipped it yesterday)
  • 9am-12pm: Tamiami Trail Everglades drive + airboat tour
  • 12pm-3pm: Tigertail Beach Marco Island (skip if running behind)
  • 3:30pm-6:30pm: Naples Tin City shopping + dinner
  • 8:30pm: Check in Venice/Caspersen Beach area

Flexibility note: Tight on time? Skip Tigertail Beach and save 2+ hours. You’ll still get the Everglades experience and Naples waterfront, and you have Caspersen Beach for shelling tomorrow.

Optional Start: Robert Is Here Fruit Stand

Hours: Opens at 9am daily

Time needed: 15-20 minutes

If you skipped this yesterday and you’re into exotic fruit, tropical smoothies, and a quirky petting zoo, stop here on your way out of Homestead. It’s the same fruit stand mentioned on Day 8 – iconic since 1959, with fruit you’ve never heard of (mamey, sapodilla, lychee, dragon fruit) plus the best Key lime milkshakes in South Florida. Small petting zoo out back with goats, emus, and tortoises.

Skip if: You already stopped yesterday, you’re not into roadside attractions, or you want to maximize Everglades time.

🐊 Everglades “Gator Alley” Drive – US-41 Tamiami Trail

The Drive:

US-41 (Tamiami Trail) cuts straight through the Everglades, and it’s hands-down the best place in Florida to see alligators. You’ll spot them right from your car while driving – sunbathing on canal banks, crossing the road, just hanging out. They’re everywhere, especially in the morning when it’s sunny. No hiking, no swamp trudging required. Pull over at the canal viewpoints if you want a closer look or better photos, but honestly, you’ll see dozens just from the driver’s seat.

🐆 Panther Crossing Signs:

Keep your eyes peeled for the “Panther Crossing” signs along this stretch – Florida panthers are critically endangered, and this is one of their last habitats. We’ve driven this road a dozen times and STILL haven’t spotted one in the wild. If you do? Send us a pic – we’re jealous! 😄

🚤 Everglades Airboat Tour

This is THE Everglades experience. Airboats skim across the shallow water at high speed, getting you deep into the sawgrass marshes where you’ll see gators, birds, turtles, and maybe even a snake or two. The guides are entertaining, the rides are thrilling, and it’s honestly one of the highlights of the whole trip.

Top Airboat Tour Options along US-41:

  • Coopertown Airboats – One of the oldest operators, 30-40 min tours, small boats (better for close-up views), ~ Child $21.40 Adult $39
  • Gator Park – Bigger operation with gator shows, longer tours available, family-friendly, ~$25-35/person
  • Everglades Safari Park – Large facility with multiple tour times, gator wrestling shows (if you’re into that), ~$39/person

💡 Pro tip: There’s an $8 park entrance fee to access the airboat tour areas. If you bought the America the Beautiful pass (mentioned in the pre-trip gifts), it covers this – just show your pass. Another reason that $80 pass pays for itself on this trip.

🛣️ Optional: Loop Road (If You Have Extra Time)

Location: Off US-41, about 20 miles west of the Shark Valley Visitor Center

Time: 30-60 minutes (it’s a slow, bumpy dirt road)

Why it’s cool: Even MORE wildlife, fewer people, old-Florida vibes

Love dirt roads? Loop Road is calling your name. This 24-mile scenic dirt/gravel loop peels off US-41 and takes you DEEP into the Everglades – narrow, bumpy, totally worth it if you’re into that backcountry adventure vibe. Tons of bird life, more gators, and a real sense of being “out there” with zero tourists. If you’re the type who gets excited about dirt roads and raw Florida wilderness, absolutely do this.

Skip if: You’re already running behind or you just want to keep moving toward Marco Island.

🏖️ Optional Adventure: Marco Island – Tigertail Beach

Time needed: 1.5-2 hours

Parking: $10/day

Why it’s special: A hidden lagoon beach with knee-deep shells and total seclusion

Here’s the deal: Tigertail Beach isn’t your typical “park and plop on the sand” beach. To get to the GOOD part – the secluded sandbar beach where shells pile up to your knees – you have to wade through a shallow lagoon. It’s an adventure, not just a beach stop. And that’s exactly why it’s amazing.

What to expect:

Park, walk through the main beach area, then wade across a calm, shallow lagoon (waist-deep depending on tide) to reach a long, pristine sandbar called Sand Dollar Spit. The shells here are INSANE – sand dollars, conchs, fighting conchs, augers, cones – serious shelling. Hardly anyone makes the wade, so you’ll have the whole beach practically to yourselves.

🌊 Tide tip: The lagoon depth changes with the tide. Best time to cross is at low tide if you’re carrying gear. The marked floating buoy shows the best crossing spot (about 50 yards). Just don’t wander too far north if the tide is going out – you might have to wade back through deeper water when it comes back in. No big deal, just something to keep in mind.

Don’t want to wade? You CAN walk around the lagoon to the south – it takes about 20 minutes through sand. Park at the far south end of the parking lot to make the walk shorter. Still gets you to the same amazing beach, just takes longer.

⏰ Tight on time? Skip this.

Tigertail adds 2+ hours to your day (plus the detour off your route). If you’re running behind schedule or want to get to Naples earlier, skip it without guilt. You’ll still have Caspersen Beach tomorrow for shark tooth hunting, so you’re not missing out on beach time entirely.

Go if: You want to wade through a lagoon to reach a secret sandbar beach that most people never find. This is one of the only beaches in Florida where you literally have to cross water to get to the good stuff – and that makes it feel like you discovered something special. The shelling is incredible, the seclusion is unbeatable, and your teenagers will love telling people they had to wade through a lagoon to get there. This is exploration, not just another beach day.

Skip if: You’re on a tight schedule, hate getting your feet wet, or just want to keep the day moving.

🛍️ Naples – Tin City Waterfront Shopping & Dining

What is Tin City?

Tin City is a collection of waterfront shops and restaurants housed in ACTUAL old tin-roofed buildings that used to be oyster processing plants and fishing shacks. This isn’t some fake “old Florida” tourist trap – these buildings are the real deal from the 1920s-1940s, now filled with local boutiques, souvenir shops, and casual seafood restaurants right on the water. Boats cruise by, the tin roofs shine in the sun, and the whole place has this authentic coastal Florida charm you can’t fake. It’s not huge, but it’s one of those spots that feels different from every other waterfront shopping area. Worth the stop for dinner with water views or just to walk around and soak it in.

Time needed: 1-2 hours

Perfect spot for dinner with waterfront views, or just walk around and enjoy the atmosphere before driving to Venice.

Where to Stay Tonight: Venice/Caspersen Beach Area

After Naples, drive about 2 hours north to the Venice area. You’re positioning yourself near Caspersen Beach for shark tooth hunting tomorrow morning. Venice/Sarasota is also home to hand-feeding flamingos at Jungle Gardens and the best Gulf Coast beaches.

Real talk on Venice hotels: They’re pricey because this area is THAT good. Venice/Sarasota might be the best stretch of Florida. I searched hard for the most affordable clean, safe options – filtered out bug reviews and sketchy spots. These aren’t fancy, but you’re paying for location in one of Florida’s most beautiful beach towns. Worth every penny for the shark teeth and flamingos tomorrow.

All prices include taxes and are based on February 2026 bookings.

Budget-Friendly Options

South Venice / Nokomis (easy 10-15 min drive to Caspersen):

Home2 Suites by Hilton Nokomis Sarasota Casey Key – $304/night
Newer hotel, suites with kitchenettes, outdoor pool, fitness center, free breakfast. About 1.2 miles from Nokomis Beach.

Holiday Inn Express & Suites Nokomis – Sarasota South – $263/night
1.2 miles from Nokomis Beach, free breakfast, pool, fitness center. Reliable chain hotel.

Near Venice Beach (Closest to Beach)

Inn at the Beach – $188/night 👈 Best location pick
Right across the street from Venice Beach, pool, beach gear to borrow (chairs, umbrellas, boogie boards), walkable to downtown Venice. Premium location.

Note: Feb dates aren’t loaded in their system yet (shows “sold out” but they’ll open up). Pricing shown is based on similar dates – call the hotel directly or check back in a few weeks for actual Feb availability.

Inland Venice (Off I-75, Budget Options)

Best Western Plus Ambassador Suites Venice – $246/night
Off I-75, all-suite hotel with free breakfast, outdoor pool, spacious rooms with microwaves/fridges. About 15 min from Venice city center and beaches.

Fairfield Inn & Suites by Marriott Venice – $291/night
Off I-75, free breakfast, outdoor pool, fitness center, free bikes to borrow.

Hampton Inn & Suites Venice Bayside South Sarasota – $290/night
Off I-75, free breakfast, pool, reliable Hampton brand. Easy access to highway for tomorrow.

Everglades & Naples Gift Ideas

  • Everglades airboat tour tickets – Main attraction, ~$28-35/person (or included in Go City Pass if using your 2nd day here)
  • Naples Tin City restaurant gift card – For waterfront dining

Day 9 Budget Snapshot

CategoryCostNotes
Hotel$188Venice area – Inn at the Beach (Best Western inland = $246)
Food$70Lunch on the road, dinner in Naples
Activities$0Free gator viewing (airboat $28–35, Tigertail Beach $10 optional)
DAILY TOTAL$258Add airboat tour if not using Go City Pass

Day 10: Venice Florida – Shark Tooth Hunting & Beach Town Vibes (Budget: $258)

Caspersen Beach

Why here: Venice is the “Shark Tooth Capital of the World,” and today you’re hunting fossils at Caspersen Beach, flying through the air at a trapeze academy, hitting up a YouTuber’s ice cream shop, and exploring quirky downtown sculpture hunts. This is action-packed Florida at its weirdest and best.

Day 10 Plan: Shark Teeth & Venice Adventures

Suggested flow:

💡 You’re staying in the same hotel as last night – no packing, no checkout. Just explore Venice all day.

🦈 Shark Tooth Hunting at Caspersen Beach (Morning)

The game plan:

  • Best timing: Lower tide is ideal, but you can find teeth all day
  • Where to look: Right after the drop-off where the beach slopes into the water – that’s where the waves wash back and leave dark patches of shells and teeth. Check those dark spots and the little dips along the waterline.
  • How: Scoop sand/shells into your sifter → shake in the water → look for jet-black triangles (root + point)
  • Depth: Knee- to waist-deep water for an adult
  • What you’ll find: Lots of small shark teeth (¼–1″), occasional larger pieces or broken “meg” fragments, stingray barbs (look like long, sharp black spikes), stingray tooth plates (flat, textured pieces). All are worth keeping!

Accessibility tip for anyone who can’t get in the water: Have the waders scoop sand and shells in the sifter, swish it in the water to rinse out the sand, then bring the sifted material to shore. Set it on a towel or use the sifter basket as a sorting tray. Now everyone can look for teeth together – no one’s stuck on the beach just watching! Perfect for keeping grandparents, little kids, or anyone with mobility issues in on the action.

Etiquette & safety:

  • Do the stingray shuffle (drag your feet instead of stepping)
  • Give wildlife space
  • Fill in holes you dig
  • Pack out trash
  • Use reef-safe sunscreen
  • Only collect white/bleached sand dollars (dark/fuzzy ones are alive – illegal to take!)

Free Activities (Venice Afternoon/Evening)

Danny’s Cream Pies – Opens at noon
YouTuber Danny Duncan’s ice cream shop in Englewood (10 min south of Venice). Ice cream + merchandise. Teenagers who follow him will LOSE IT. Located at 505 W Dearborn St, Englewood. Open 12pm-6pm daily.

Venice Shark Sculpture Hunt – Free
1-mile downtown walking loop finding 10 bronze shark sculptures (about 10″ long) hidden around shops and streets. Start at Centennial Park splash fountain. Use clues at visitvenicefl.org/sharks. Takes 45-60 minutes. It’s like a treasure hunt through downtown.

Venice Fairy Door Hunt – Free
30+ tiny fairy doors hidden high and low throughout downtown. Might be too cutesy for some teens, but fun for finding a few while you’re exploring.

Downtown Venice Shopping & Eating – Free
Historic Mediterranean-style downtown with local boutiques, ice cream shops, cafes. Just walk around and soak it in.

Centennial Park splash fountain & more – Free interactive splash pad (open 9:30am-9:30pm) – great if you have younger kids who need to cool off after beach hunting. The park also has a pretty gazebo that hosts free Friday night concerts (bimonthly – check Venice MainStreet calendar), picnic tables under Banyan trees, restrooms, and it’s the starting point for the shark sculpture hunt. Big city events happen here too (festivals, holiday parades, etc.).

Venice Fishing Pier – Free
700-foot pier with Gulf views. Walk it for free, great sunset spot.

Paid Activities

Tito Gaona’s Flying Trapeze Academy – $45/person for 1.5-hour class
TEENAGERS WILL LOVE THIS. Learn to fly on an actual trapeze with safety harnesses and nets. World-renowned trapeze family teaches you. This is legit professional equipment – you’re flying through the air catching and swinging. Classes: Wed & Fri 5-6:30pm, Sat 10am-11:30am. Must book ahead at titogaona.com or call 1-866-TRAPEZE.

Warm Mineral Springs – $20/adult, $15/ages 6-17
Florida’s ONLY natural warm spring (85°F year-round). If the ocean is wavy or rough, this is your backup swimming spot. It’s a 250-foot-deep sinkhole with healing mineral water. Open 9am-5pm. About 15 min east of Venice in North Port. Bring pool noodles! Archaeological site with prehistoric fossils found at the bottom. Located at 12200 San Servando Ave, North Port.

Shark Frenzy Store – Downtown
Shop where experts identify and authenticate your shark teeth finds. Free to browse, teeth for sale ~$5-15 if you didn’t find any.

Venice Theatre – ~Starting at ~$20/person (varies by show)
For those who can’t stand missing local events: this is one of the largest community theaters in the U.S. Shows, musicals, concerts throughout the year. If you’re the type who Googles ‘concerts near me’ in every city, check their schedule before your trip. You might find something perfect.

Kayak Rentals – ~$20-50/hour
Explore Venice waterways and mangroves.

Ideal Classic Cars Museum – FREE – More than a dealership – it’s a museum dedicated to American automotive legends, and the door’s always open. Boss 429 Mustangs, ’67 Corvettes, cars you’ve seen in movies and dreamed about since you were sixteen. The team is passionate, welcoming, and wants you there even if you’re not buying. They call it ‘standing in the presence of greatness’ – car people will absolutely love this. Non-buyers welcome, totally free.

Legacy Trail Bike Rentals – ~$35/day
For active families who’d rather bike than drive everywhere. This paved 18.5-mile trail connects Sarasota to Venice with a new 4-mile extension ending right at Venice Beach (where you’re shark tooth hunting anyway). Rated as a must-do scenic experience. You don’t have to do the whole trail – rent for a few hours, explore part of it, bike to the beach instead of driving. Makes the day more memorable than just car-to-beach-to-car.

Venice Gift Ideas

Where to Stay Tonight

Stay in the same hotel as last night (Day 9). You’re already unpacked, you know where everything is, and Venice is perfectly positioned for tomorrow’s drive to Sarasota (only 30 minutes north).

Day 10 Budget Snapshot

CategoryCostNotes
Hotel$188Second night, same hotel (Inn at the Beach)
Food$70Beach picnic, ice cream, downtown dining
Activities$0Free beach + downtown (trapeze $45, Warm Mineral Springs $20 optional)
DAILY TOTAL$258Add paid activities if desired

Day 11: Sarasota & Fort De Soto – Flamingos, Shelling & Sunset (Budget: $203.50)

Sarasota Jungle Gardens

Drive: Venice → Sarasota (30 min) → Fort De Soto (45 min) → Pass-a-Grille (20 min)

Why this flow: Late-morning flamingos after they open at 10am, beach-and-fort afternoon with AMAZING shelling, then sunset at Pass-a-Grille’s old Florida charm.

Day 11 Plan: Beach Day with Wildlife

Suggested flow:

🦩 Sarasota Jungle Gardens

Admission: $24.99/adult, $14.99/child (4-12), FREE under 4

This is what you came for: HAND-FEEDING FREE-ROAMING FLAMINGOS. These birds literally walk right up to you and eat out of your hands. It’s not a “look but don’t touch” situation – you’re IN the habitat with them, feeding them, and they’re completely unbothered by people.

What else is here:

  • 1.2 miles of shaded jungle trails (10 acres, paved paths, stroller/wheelchair friendly)
  • Petting zoo
  • Reptile encounters
  • Photo ops with parrots and alligators
  • Multiple bird shows throughout the day

What to bring:

  • Cash for flamingo food (buy the bag at entrance – better deal and easier to carry than feeding coins into vending machines)
  • Water
  • Hand wipes

🏖️ Fort De Soto Park

Park entry: $6/vehicle

Cost to get there: $1.25 in bridge tolls ($0.50 + $0.75) – accepts SunPass or cash

Park entry: $5/vehicle

Total cost: $6.25 (one-way tolls + parking)

Fort De Soto is consistently rated one of America’s best beaches, with a historic Spanish-American War fort, incredible shelling (sand dollars galore!), and water that’s usually clearer than most Gulf beaches. Yes, it costs $6.25 to get in (tolls + parking), but it’s worth every penny. This is one of the best beach experiences in Florida.

💡 Return trip: You’ll pay the tolls again on the way out ($1.25), so budget $7.50 total for Fort De Soto access.

Free Activities at Fort De Soto

Historic Fort De Soto + Beach – FREE once you’ve paid parking
The beach right behind the fort is THE spot. We’ve found hundreds of sand dollars here – literally hundreds. Starfish, octopus, and squid wash up too (not as often, but it happens). It’s a beach, so conditions change, but we’ve never been disappointed. The water is clearer than most Gulf beaches. Walk through the 1898 fort with mortars and cannons first, then hit the beach for shelling.

💡 Shelling tip: Only collect white/bleached sand dollars – those are dead and legal to take. If it’s dark (brown/purple) or fuzzy, it’s alive – put it back! Taking live sand dollars is illegal in Florida.

Gulf Pier or Bay Pier Walk – FREE
700+ foot piers for sunset views and dolphin watching. FREE to walk (fishing requires license). Open 7am-sunset.

7-Mile Paved Bike Trail – FREE
Connects all the beaches if you want to explore on foot or rent bikes.

North Beach Lagoon – FREE
Calm, gentle water perfect for swimming.

Paid Activities at Fort De Soto

Kayak or Paddleboard Rentals – ~$20-50/hour (cashless only)
Explore the mangroves and keys. All concessions are cashless.

Beach Chair & Umbrella Rentals – Available at North Beach swim center (cashless only)

Bike Rentals – ~$20-40/day (cashless)
To ride the 7-mile trail.

Pro tips:

  • Park at the fort parking lot for easy access to both fort AND the best shelling beach
  • Bring containers for sand dollars – they’re super fragile and will break in a mesh bag. Use yogurt containers, butter bowls, or cheap Tupperware from home. Or grab [these inexpensive stackable containers] that are perfect for beach finds. Mesh bags work great for regular shells.
  • All concessions are cashless

🌅 Pass-a-Grille Beach (Old Florida Sunset)

Drive: ~20 min from Fort De Soto

Why it’s special: Quietest, most laid-back beach on the island – 4 miles of powder-soft sand with almost no buildings directly on the beach (just historic cottages back from the dunes). This is old Florida at its best.

What’s here:

  • Historic 8th Avenue with boutiques, ice cream shops, outdoor art market (walking distance from beach)
  • Brass Monkey– Casual beachfront dining for sunset dinner
  • Known as one of the best sunset spots in the area
  • Metered parking along Gulf Boulevard (not free, but usually available)
  • Free Freebee ride service to get around if you want to park once and explore

Where to Stay Tonight: St. Pete Beach / John’s Pass / Madeira Beach Area

After sunset at Pass-a-Grille, drive about 15 minutes north to the St. Pete Beach/John’s Pass area. You’re staying here for 2 nights (tonight and tomorrow), so you won’t have to pack up again until Day 13.

Real talk: This stretch doesn’t have a ton of budget-friendly options, but here’s what works:

All prices include taxes and are based on February 2026 bookings.

Budget Options (Under $150/night)

La Quinta Inn & Suites by Wyndham Clearwater South – $126/night 👈 Best budget pick
Chain reliability, about 15 min from the beach, solid budget option.

Tropical Inn & Suites – $147/night
Basic amenities, gets you in the area without breaking the bank.

Holiday Isles Resort – $149/night
Family studio rooms, no-frills but functional.

Best Location (Walk to John’s Pass & Beaches)

John’s Pass Hotel – ~$199 + tax/night
Literally ON the boardwalk with unbeatable location. Requires 2-night minimum stay. Reviews are mixed, but if you want to slow down at the end of the trip and skip packing/unpacking, this spot lets you walk everywhere.

Blind Pass Resort Condo-Motel – $270/night
Old-school Florida with efficiency units, right between St. Pete Beach and Treasure Island, steps to the beach.

Farther Out (Cheaper, More Driving Tomorrow)

Extended Stay America Suites – Tampa Airport – $179/night
Suite with kitchenette, but 30+ min from beaches. Only worth it if you need to save and don’t mind the drive.

Holiday Inn St. Petersburg N- Clearwater – $161/night
Off I-275, free breakfast, about 20 min from beaches.

Sarasota & Fort De Soto Gift Ideas

Day 11 Budget Snapshot

CategoryCostNotes
Hotel$126St. Pete Beach area budget option (John’s Pass Hotel = $199)
Food$70Breakfast, lunch, sunset dinner
Park Entry$7.50$5 parking + $2.50 round-trip tolls
Activities$0Free beach/shelling (Jungle Gardens $25/person optional)
DAILY TOTAL$203.50Add Jungle Gardens if not using Go City Pass

Day 12: John’s Pass & Clearwater Beach – Dolphins & Pier 60 Sunset (Budget: $196)

Pier 60

Drive: You’re already in the area! John’s Pass is walkable if you stayed at John’s Pass Hotel, or a short 5-15 min drive from other area hotels. Clearwater Beach is about 20-30 min north.

Today is all about classic Florida beach town vibes – dolphin watching from the boardwalk, browsing shops, walking iconic piers, and catching the nightly sunset festival at Clearwater’s Pier 60. No rush, no big drives, just soaking in the Gulf Coast.

Day 12 Plan: Beach Towns & Boardwalks

Suggested flow:

🐬 John’s Pass (Madeira Beach)

What is John’s Pass?

John’s Pass is a historic fishing village turned boardwalk destination – wooden walkways over the water lined with quirky local shops you won’t find anywhere else. Think Addicted to the Bean coffee shop, Dick’s Last Resort for loud and rowdy dining, and Big Dick’s Salty Seaman Fun Shop for hilarious souvenir shirts your teenagers will beg for. Mix in boat tours, waterfront restaurants, and dolphins swimming right through the pass multiple times a day. You’ll see them from the boardwalk without even trying. It’s free to walk around, soak in the small-town atmosphere, and watch the boats and wildlife. This isn’t a mall – it’s a real Florida fishing village with personality.

What’s here:

  • Free boardwalk with water views on both sides
  • Dolphin watching from the boardwalk (they swim through the pass – just watch and wait)
  • Local shops, souvenir stores, beach gear
  • Casual waterfront restaurants
  • Boat tour options (paid)

Time needed: 2-3 hours to explore, eat, and dolphin watch

Free Activities at John’s Pass

Boardwalk Walk & Dolphin Watching – FREE
Just walk the boardwalk and watch the water. Dolphins swim through the pass regularly – morning and late afternoon are best times. Bring your phone or camera and be patient. You WILL see them.

Browse the Shops – FREE
Tons of beachy gift shops, souvenir stores, hermit crab vendors (yes, really), and local art. Free to browse.

Watch the Boats – FREE
Fishing charters coming and going, parasailing boats, tour boats – it’s an active working waterfront. Fun to just sit and watch.

Paid Activities at John’s Pass

Dolphin Tour Boat Rides – ~$29.95/person
Narrated dolphin-watching tours that get you closer to the action. Most guarantee dolphin sightings. Tours are 1.5 hours.

Deep-Sea Fishing Charters – Prices vary widely
John’s Pass is a major fishing hub. Half-day trips start around $60-80/person, full-day trips more.

Parasailing – ~$89/person
Fly above the Gulf with incredible views. Weather-dependent.

Jet Ski Rentals – ~$60-130/hour
Rent and explore the intracoastal waters.

🏖️ Clearwater Beach

Drive: ~20-30 min north from John’s Pass

Clearwater Beach is one of Florida’s most famous beaches – consistently ranked among America’s best. White powder sand, clear turquoise water (hence the name), and Pier 60’s nightly sunset festival make this a must-visit.

Free Activities at Clearwater Beach

Beach Walk – FREE
Miles of white sand beach. Walk north toward Sand Key Park or south toward the hotels – it’s all gorgeous.

Pier 60 Sunset Festival – FREE (nightly, 2 hours before sunset until 2 hours after)
This is THE reason to come to Clearwater Beach. Every single night, Pier 60 hosts a sunset festival with:

  • Street performers (musicians, magicians, jugglers)
  • Local artisans selling crafts
  • Live music
  • The sunset itself (obviously)

It’s a celebration, not just a sunset. Arrive 30-45 minutes before sunset to get a good spot and watch the performers set up. Stay after sunset to browse the artisan booths.

Walk Pier 60 – FREE during the day, parking costs extra
1,080-foot pier stretching into the Gulf. Walk it anytime for ocean views and fishing action (anglers line the rails). FREE to walk, fishing requires a license.

Paid Activities at Clearwater Beach

Beach Gear Rentals – Varies
Chairs, umbrellas, cabanas, paddleboards, kayaks – all available to rent on the beach.

Captain Memo’s Pirate Cruise – ~$45/person
Fully commit to the pirate theme or don’t bother. This 2-hour cruise is ALL IN: water gun battles, treasure hunts, firing cannons, face paint, pirate stories, dance parties. Younger kids love it unironically, older kids/adults love it ironically with complimentary beer and wine. Dolphin watching happens too. The crew speaks only pirate (yes, really). It’s cheesy, it’s ridiculous, it’s genuinely fun if you embrace it. Book 2-3 days ahead.

Clearwater Marine Aquarium – ~$41.95/adult, FREE with Orlando Go City Pass – Home of Winter the famous dolphin from Dolphin Tale, and she’s just the star of a much bigger mission. This is a working marine rescue – real animals being rehabbed and released, not just pretty tanks. See sea turtles, otters, sharks, and learn about actual conservation work happening right there. Way more interesting than typical aquariums. Great rainy-day backup or air-conditioned break from beach days.

Where to Eat

John’s Pass area:

  • Casual waterfront seafood restaurants line the boardwalk
  • Bubba Gump Shrimp Co. (if you didn’t hit it earlier)
  • Lots of fried seafood baskets, fish tacos, grouper sandwiches

Clearwater Beach:

  • Frenchy’s Rockaway Grill – Famous grouper sandwiches
  • Beachwalk restaurants along the sand
  • Pier 60 has food vendors during the sunset festival

John’s Pass & Clearwater Gift Ideas

Where to Stay Tonight

Stay in the same hotel as last night (Day 11). You’re already unpacked and settled. Tomorrow you’ll check out and start the drive north toward home with a stop at Tarpon Springs and Weeki Wachee.

Day 12 Budget Snapshot

CategoryCostNotes
Hotel$126Second night, same hotel (La Quinta budget option)
Food$70Boardwalk lunch, beach dinner or festival snacks
Parking$0John’s Pass free parking; Clearwater Beach meters vary (~$3–5/hour if needed)
Activities$0Free boardwalks + Pier 60 festival (dolphin tour $25–40 optional)
DAILY TOTAL$196Add paid activities if desired

Day 13: Tarpon Springs & Weeki Wachee – Start the Drive Home (Budget: $160)

Tarpon Springs

Drive: St. Pete Beach area → Tarpon Springs (30 min) → Weeki Wachee Springs (1 hour) → Drive north 6+ hours into Georgia

Today you’re checking out, saying goodbye to the Gulf Coast, and starting the journey home – but not before hitting two uniquely Florida stops: Greek sponge divers in Tarpon Springs and LIVE MERMAIDS at Weeki Wachee Springs. Then it’s highway time, pushing north to break up tomorrow’s final drive home.

Day 13 Plan: Two Stops, Then Drive

Timeline:

💡 Why stop in Georgia tonight? Breaking up the drive home into two days makes it way more manageable. Where you stop tonight depends on tomorrow’s plan:

If doing Wild Animal Safari tomorrow: Stop in Macon, GA or further south (~6 hours from Weeki Wachee). This positions you for the safari in Pine Mountain tomorrow morning without backtracking.

If skipping the safari and going straight home: Push to Atlanta area (~7 hours) to knock out more miles today and have less driving tomorrow.

🧽 Tarpon Springs – Greek Sponge Docks

What is Tarpon Springs?

Tarpon Springs has the highest percentage of Greek Americans of any US city – and the second you step onto the sponge docks, you’ll know it. This isn’t some manufactured “Greek themed” tourist trap. This is a REAL working Greek community where sponge boats still go out every day using techniques passed down since Greek divers arrived in the early 1900s. You’ll hear Greek spoken on the streets, smell spanakopita baking in family-owned bakeries, watch old men arguing in Greek outside cafes, and wonder if you somehow drove to the Mediterranean instead of the Gulf Coast.

The historic sponge docks are lined with restaurants serving food made by Greek grandmas (not chain chefs), bakeries where baklava is made the right way, and shops selling natural sponges harvested from these exact waters. This is one of those places where Florida stops being Florida for a minute and becomes something completely unexpected. Don’t skip this stop.

What to do:

  • Walk the sponge docks and waterfront boardwalk (FREE)
  • Watch sponge demonstrations (FREE)
  • Browse shops selling natural sponges, olive oil, Greek imports (FREE to browse)
  • Eat authentic Greek food (baklava, gyros, spanakopita, Greek coffee)
  • Visit St. Nicholas Greek Orthodox Cathedral – beautiful Byzantine architecture (FREE, donations welcome)

Time needed: 2-3 hours to walk, eat, and explore

💡 Food tip: This is where you want to splurge on lunch if you’re going to anywhere. Authentic Greek food, waterfront dining, family-owned restaurants that have been here for generations. Skip the chain restaurants and eat Greek today.

🧜‍♀️ Weeki Wachee Springs State Park

Park entry: $13/adult, $8/child (6-12), FREE under 6

Weeki Wachee Springs is pure old-Florida roadside magic – LIVE MERMAID SHOWS performed underwater in a natural spring since 1947. Yes, really. Real people in mermaid tails performing choreographed routines underwater in a crystal-clear spring while you watch from an underwater theater. It’s kitschy, it’s nostalgic, it’s legitimately impressive (they’re holding their breath and doing flips), and it’s one of those uniquely Florida experiences you can’t get anywhere else.

What’s here:

  • Live mermaid shows (30 min, multiple shows daily) – Performed in an underwater theater carved into the spring. The mermaids breathe from air hoses hidden in the set while performing underwater ballet. It’s part synchronized swimming, part vintage Americana, all Florida weird.
  • Buccaneer Bay water park (seasonal, included with admission) – Springs-fed swimming area with slides and sandy beach
  • Paddleboarding and kayaking the Weeki Wachee River – Rentals available, beautiful crystal-clear spring-fed river
  • Wilderness River Cruise – Guided boat tour through pristine Florida nature

Show schedule: Check website for current show times – they run multiple times per day but vary by season. Plan to arrive at least 30 minutes before showtime.

Time needed: 2-3 hours (longer if swimming or paddling)

💡 Pro tip: This is one of those places that could feel touristy and cheesy, and it IS – but that’s the charm. It’s been doing the exact same show since 1947. Embrace the vintage Florida roadside attraction vibes. Your teenagers might roll their eyes going in, but they’ll be talking about the mermaids for years.

The Drive North (Afternoon/Evening)

After Weeki Wachee, it’s time to point the car north and start chewing up miles. You’re looking at 6-8 hours of driving today depending on where you stop for the night.

Route: Take I-75 North through Florida, into Georgia

Suggested overnight stops in Georgia:

Hotel strategy: Book something basic and cheap – you’re just sleeping and hitting the road again in the morning. Look for:

💡 Driving tip: Stop for dinner before you get too tired. Eat, stretch your legs, fuel up the car, then push the final hour or two to your hotel. Don’t try to power through hungry and exhausted.

Where to Stay Tonight: Georgia

After your long drive north, you’ll overnight somewhere in Georgia. This is purely a practical sleep stop – nothing fancy needed.

Budget hotel options (approximate pricing for Georgia):

💡 Book flexible: Since you don’t know exactly when you’ll want to stop driving, consider booking a hotel with free cancellation, or just stop when you’re tired and find something using a hotel app.

Day 13 Budget Snapshot

CategoryCostNotes
Hotel$90Georgia overnight (budget chain hotel estimate)
Food$70Greek lunch in Tarpon Springs, dinner on the road
Gas$0~6–8 hours driving (~$50–70 gas)
Activities$0Free Tarpon Springs (Weeki Wachee $13/adult optional)
DAILY TOTAL$160Add gas (~$50–70) + Weeki Wachee admission if visiting

Day 14: The Final Drive Home (Budget: $70)

Safari

Drive: Georgia → Home (Detroit area: 10-13 hours remaining depending on where you stopped last night)

The final day of your Florida adventure – and yes, the drive IS part of the adventure! You’ll watch the landscape change from Georgia pines to your home state, relive the highlights with your family, and maybe even spot a few more roadside oddities on the way. Today’s about enjoying the journey home, making one last memory at the Wild Animal Safari if you want, and rolling into your driveway with stories to tell for years.

Day 14 Plan: The Road Home

Timeline:

  • Morning: Check out, grab breakfast, fuel up
  • Optional: Wild Animal Safari – feed giraffes from your car window (~2 hours)
  • Highway time: Music, podcasts, road trip games, and family recap of the best moments
  • Evening: Home! Unload the essentials, order pizza, and collapse happy

💡 Make it fun: This is the day everyone shares their favorite moment from the trip, argues about which beach was best, and makes plans for next year. The drive home is when all the memories come together.

🦁 Optional Stop: Wild Animal Safari (Pine Mountain, GA)

Location: About 1 hour south of Atlanta off I-85
Admission: $89.99 for family 4-pack
Time needed: 1.5-2 hours for the drive-through

💡 If you only pay for ONE thing on this entire trip, make it this. Seriously. For $89.99, your family of 4 gets to drive through habitats where zebras, giraffes, camels, and more roam free and come RIGHT up to your windows.

Here’s what makes it worth it:

  • Buy the feed buckets at the entrance ($5.25-$5.75) – this is NOT optional, this is THE experience
  • Animals recognize the feed buckets and literally mob your car
  • Giraffes stick their heads IN your car windows to eat from your hand
  • Zebras, llamas, and camels come right up
  • Your teenagers will lose their minds (and take 500 photos)

Pro tips:

  • VIDEO THIS – Forget photos, you want VIDEO. A giraffe sticking its entire head in your car while your teenager screams and laughs? That’s a video you’ll watch for years. Photos can’t capture the chaos.
  • Driver tip: You control the window locks – When that massive buffalo head comes through someone’s window and they’re screaming to close it? You can lock the windows OPEN for a few extra seconds. Buffalo are gentle – they just don’t know how BIG they are. The panic is pure entertainment. Mean? Maybe. Hilarious? Absolutely. (Your passengers don’t need to know the buffalo is harmless.)
  • Buy 6 feed buckets for a family of 4 (1 per person and 2 for everyone to split when they run out)
  • Drive slow – animals are everywhere and have zero fear of cars
  • The drive-through takes 1 to 2 hours depending on how long you linger
  • Your car will get messy – Food pellets scattered everywhere, animal drool on the windows, dusty hoofprints on the doors. That’s part of the experience. You bought your car to TRAVEL, not to keep it museum-perfect.

Go if: You’re breathing. Skip only if there’s a legitimate emergency. This is one of the best stops on the entire trip – giraffes in your car, zebras everywhere, pure chaos in the best way. Everyone from toddlers to grandparents will be laughing and screaming. Don’t overthink it, just go. You’ll talk about this for years.

Day 14 Budget Snapshot

CategoryCostNotes
Hotel$0Last night in Georgia (already counted on Day 13)
Food$70Breakfast + road snacks
Activities$0Free drive home (Wild Animal Safari $89+food optional)
DAILY TOTAL$70

Frequently Asked Questions:

Planning & Budget Questions

How much does a vacation for a family of four cost in Florida?

For this 14-day Florida road trip (driving from Detroit), expect to budget approximately $2,935 for the baseline trip (gas, food, hotels, and parking/tolls), or $3,811 if you add the Go City Pass for 20+ attractions. This includes gas both ways, 13 nights of hotels (mid-range options), and food. You can significantly reduce costs by choosing budget hotels, packing picnic lunches, and skipping paid attractions in favor of free beach days. The beauty of this itinerary is that families can chip in together – parents gift the trip, grandparents wrap experience vouchers, and aunts/uncles contribute gift cards – making it more affordable for everyone.

Should we fly or drive to Florida for this trip?

This itinerary is designed for driving since you’re doing a full coastal loop with 13 different overnight stops. Flying into Orlando and renting a car could work, but you’d need to either skip the beginning (Savannah/St. Augustine) or do a lot of backtracking. Driving from Michigan gives you maximum flexibility, lets you pack everything you need, and turns the journey into part of the adventure. If you do fly, consider starting in Miami instead of Orlando to better match the itinerary flow.

Do we need to book hotels in advance for this Florida trip?

Yes – book 3-8 weeks ahead, especially for Key West, Miami Beach, and Clearwater. Here’s why: I learned this the hard way. Tried winging it once and paid close to $200/night for rooms I could have prebooked for $35-100. Florida’s budget hotels fill up fast during February-April, and as cheap rooms disappear, prices skyrocket. You’re not just locking in availability – you’re locking in PRICES. Book Key West and Miami earliest (6-8 weeks), smaller stops like Venice and Daytona can be 3-4 weeks out. Want flexibility? Book hotels with free cancellation, but get those reservations in early or you’ll pay double.

What can we skip if we only have 10 days instead of 14?

If you need to shorten the trip, here’s what to cut: Skip Day 6 (Cocoa Beach) and drive straight from Orlando to Miami. Combine Days 9-10 (Everglades and Venice) into one day by skipping some beach stops. Cut Day 11 (Sarasota/Fort De Soto) and drive straight from Venice to St. Pete area. This gives you: Savannah, St. Augustine, Daytona, Orlando/Kissimmee, Miami, Key West, Naples area, Clearwater/Tarpon Springs, and Weeki Wachee before heading home. You’ll still hit the major highlights without feeling rushed.

What’s the best time of year to visit Florida with family?

For this itinerary, late January through April is ideal – warm enough for beach and water activities without the brutal summer heat and afternoon thunderstorms. Spring break timing (March/early April) gives you the best weather but also bigger crowds and higher hotel prices. February offers a sweet spot: good weather, lower prices, and manageable crowds. Avoid summer (June-August) for this trip – it’s hot, humid, and afternoon storms can derail outdoor plans. Winter holidays (Christmas/New Year’s) are expensive and crowded.

Gift-Giving Questions

How do you gift a vacation for Christmas when you want something under the tree?

The trick is breaking the trip into tangible, wrap-able pieces. Instead of just handing over a piece of paper that says “We’re going to Florida!”, wrap actual items they’ll use on the trip: snorkel gear for the Keys, a new beach towel, waterproof phone case, sunglasses, or a travel journal. For experiences, print and wrap vouchers for specific activities – airboat tours, dolphin cruises, restaurant gift cards, or attraction tickets. Get creative with presentation: put Key West trolley tour tickets inside a Florida-themed mug, or wrap shark tooth hunting supplies with a note about Venice Beach. This approach gives kids the excitement of opening gifts on Christmas morning while building anticipation for the upcoming adventure. Bonus: it lets extended family participate – grandparents can wrap the snorkel gear, aunts and uncles can give gift cards, everyone chips in to make the trip more affordable.

What are good experience gifts for teenagers?

Teenagers love experiences over stuff – especially when those experiences create memories with family. Great experience gifts include: attraction tickets (like airboat rides or snorkeling tours), restaurant gift cards they can use on the trip, activity vouchers (dolphin cruises, kayak rentals), and “choice” envelopes where they pick one big experience. The key is giving them something tangible to unwrap at Christmas that builds excitement for the upcoming trip. Even practical gifts like beach towels, waterproof phone cases, or a new pair of sunglasses feel special when they’re specifically for a Florida adventure.

What is the 4 gift rule and how does this trip fit?

The 4 gift rule is: Something they want, something they need, something to wear, something to read. This Florida trip works perfectly: The TRIP is what they want. Practical gear like snorkel sets, beach towels, or a waterproof camera is what they need. A new swimsuit, sun hat, or trip-specific clothing is something to wear. A travel journal or Florida guidebook is something to read. By spreading the trip across multiple gift-givers and categories, you create a pile of presents under the tree while staying within thoughtful gifting frameworks.

Family & Age Questions

What are the best things to do in Florida with teenagers?

Teenagers want experiences that feel adventurous, not babyish – and Florida delivers. Top hits: snorkeling in the Keys (they’ll talk about the reef for years), airboat rides through the Everglades (gators up close!), driving on Daytona Beach, exploring Key West’s quirky vibe, kayaking through mangroves, and hunting for shark teeth on Venice Beach. Skip the character meet-and-greets and focus on activities where they feel independent – walking historic St. Augustine, choosing their own food at John’s Pass, or exploring Fort Zachary Taylor. The secret? Keep the pace fast and varied. Teenagers get bored sitting still, so this itinerary moves every day with new scenery, different activities, and plenty of “Instagram-worthy” moments they’ll actually enjoy.

What can I show my teenage grandkids in Florida?

If your grandkids are visiting Florida and you want to impress them, focus on unique experiences they can’t do at home. Take them on an airboat tour in the Everglades – nothing beats seeing gators in the wild. Drive through Wild Animal Safari in Pine Mountain where giraffes stick their heads in your car window. Show them Key West’s sunset celebration at Mallory Square with street performers and ocean views. Let them drive on Daytona Beach (if they have a license) or hunt for fossilized shark teeth at Venice Beach – they can actually keep what they find! For a full adventure, use this 14-day itinerary where each day offers something different. The beauty? Grandparents can chip in by gifting specific experiences – wrap dolphin cruise tickets, a restaurant gift card, or snorkel gear – so you’re part of making the trip memorable without footing the entire bill.

Is this Florida trip better for teenagers or young kids?

This itinerary is designed specifically for teenagers and tweens (ages 10+). It’s fast-paced with lots of driving, exploring, and activities – not a relaxing resort vacation. We skip character meet-and-greets and kiddie attractions in favor of snorkeling, kayaking, beach time, historic sites, and unique experiences like Key West and the Everglades. If you have younger children (under 8), you might want to slow down the pace, add more pool days, and swap some activities for theme parks. But for teenagers who want adventure and variety? This hits perfectly.

Practical Travel Questions

How do you keep kids entertained on a long road trip?

Road trips are built-in entertainment if you plan ahead. Download podcasts or audiobooks the whole family enjoys (Audible membership makes a great gift!). Play classic road trip games like license plate bingo, 20 questions, or “would you rather.” Let teenagers control the music playlist for an hour, then switch. Stop every 2-3 hours to stretch, grab snacks, or explore quick roadside attractions. The drive from Detroit to Florida takes 13-15 hours, so break it into two days with an overnight in Kentucky or Tennessee. Phones and tablets are fine for part of the trip, but some of the best family conversations happen when everyone’s stuck in the car together – embrace it.

What should I pack for a 2-week Florida road trip?

Pack layers – mornings can be cool in February, but afternoons warm up. Essentials: swimsuits, sunscreen, water shoes, beach towels, snorkel gear, flip-flops, one nice outfit for dinners, comfortable walking shoes, hats, sunglasses, and a reusable water bottle for each person. Bring a cooler for drinks and snacks. Don’t overpack clothes – most hotels have laundry. Check our complete packing list in the “Pre-Trip Gifts” section for everything you’ll need, organized by category. Pro tip: Pack shark tooth sifters and containers for Venice Beach – you’ll thank us later.

Is it safe to drive through Florida at night?

The interstates and major highways (I-95, I-75, US-1) are well-lit and heavily traveled, so nighttime driving is generally safe. However, wildlife (especially deer) is more active at dusk and dawn in rural areas. If you’re driving the Tamiami Trail through the Everglades, stick to daytime – it’s more about seeing the scenery and wildlife than safety. For this itinerary, you’ll occasionally drive after dark (like returning from Key West or driving to Georgia on Day 13), but it’s all on major routes. Just stay alert, take breaks when tired, and don’t push through exhaustion.

Can you really drive on Daytona Beach?

Yes! Daytona Beach is one of the few beaches in America where you can legally drive and park your car right on the sand. You’ll pay a beach access fee (around $20/vehicle) at the entrance toll booths. The sand is firm-packed and safe to drive on – just follow posted speed limits (10 mph), watch for pedestrians and soft sand near the water, and park in designated areas. It’s surreal and fun – you can literally pop your trunk and set up beach chairs without carrying anything. Just make sure your windows are up when you leave your car, and rinse off the salt afterwards.

Do I need a special pass for Florida state parks?

Individual state park entry fees are affordable ($5-8 per vehicle typically), but if you’re visiting multiple parks on this trip, consider the America the Beautiful Annual Pass ($80). It covers Fort Zachary Taylor in Key West, Canaveral National Seashore, and other federal sites – it pays for itself in 2-3 visits. Florida State Parks also offer an annual pass, but you won’t hit enough state parks on this coastal route to make it worthwhile. Just pay per entry as you go.

📧 Still Have Questions?

Planning a road trip this detailed can bring up specific questions about your family’s situation. Email us at inforoadtripowl@gmail.com with your question – we’ll help for free, no strings attached. We’re not trying to sell you anything, we just love helping families actually make these trips happen. We usually respond within 24 hours.

(And no, we won’t add you to a spam list. We hate that too.)

Friendly Disclaimer (Read Before You Book): We do our best to keep this guide accurate, but details can change without notice and we’re human – mistakes happen. Please verify key info (prices, hours, parking, age/height restrictions, cancellation/refund policies, and seasonal schedules) directly with the venue or ticket provider before you purchase. Also check recent reviews; experiences vary, and what’s great for some travelers isn’t always right for you.

This guide is for general planning only and isn’t professional, legal, or medical advice. Outdoor and water activities come with risks – choose what matches your comfort level and follow posted rules. If you see something that’s outdated, send us a quick note so we can fix it.

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