In just 3 days, you can explore white-sand beaches, scenic nature spots, waterfront dining, and amazing downtowns.
Whether you’re here for a weekend or adding this to a longer Florida road trip, this itinerary packs in the best of the region without feeling rushed.
Here’s how to spend the perfect 3 days in Southwest Florida:
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Day 1: Sarasota +Venice
Morning: Sarasota + Siesta Key
Spend your first morning in Sarasota, a vibrant city known for art and culture.
Visit the Marie Selby Botanical Gardens or explore The Ringling, which includes a museum of art, a circus museum, and stunning bayfront gardens.
No Southwest Florida trip is complete without visiting Siesta Key Beach.
It’s often ranked the #1 beach in the U.S. for good reason — the sand is soft and cool (because it’s 99% quartz), and the water is stunningly clear.
Lunch: Siesta Key Oyster Bar (SKOB)
End your time in Siesta Key with a casual, fun dinner spot that’s always buzzing.
Grab oysters, fish tacos, and drinks under string lights with live music in the background.
Afternoon and Evening: Venice Beach & Shark Tooth Hunting
End your day in Venice, one of the quirkiest towns in Southwest Florida — and the unofficial “Shark Tooth Capital of the World.”
Head to Caspersen Beach, bring a sifter or scoop, and start searching. You’re almost guaranteed to find prehistoric shark teeth in the sand!
Then stroll through Downtown Venice, filled with Mediterranean architecture, sidewalk cafes, and local shops.
Day 2: Fort Myers + Sanibel Island
Morning: Downtown Fort Myers River District
Start your trip in the heart of Fort Myers. The historic River District is packed with charming shops, cafes, and colorful murals.
Grab a coffee at Sunny Harbour Coffee or Dean Street Coffee, then take a walk along the Caloosahatchee River.
If you’re into history, stop by the Edison and Ford Winter Estates — two iconic homes turned museums, with botanical gardens and a look at Florida’s early innovators.
Afternoon: Sanibel Island
Drive about 30 minutes southwest to Sanibel Island, one of the most unique destinations in Florida.
Known for its shell-covered beaches and laid-back vibes, it’s a must-see.
Head to Bowman’s Beach or Lighthouse Beach Park to swim, explore, or hunt for shells.
Don’t miss the J.N. “Ding” Darling National Wildlife Refuge, where you can drive or kayak through mangrove forests and spot birds, gators, and manatees.
Dinner: Doc Ford’s Rum Bar & Grille (Sanibel)
Enjoy fresh seafood with water views. Try their Yucatan shrimp and a tropical cocktail — it’s the perfect end to a beach day.
Day 3: Naples + Marco Island
Morning: Naples Pier & Downtown Naples
Start your last day in Naples, where upscale meets coastal cool. Take a walk down Naples Pier, especially in the early morning when dolphins are often spotted near the shore.
From there, explore Third Street South and Fifth Avenue South — two of the most beautiful shopping and dining streets in Florida.
Think palm-lined sidewalks, art galleries, and boutiques.
Afternoon: Marco Island
Just under an hour south of Naples is Marco Island, the largest of Florida’s Ten Thousand Islands.
Head to Tigertail Beach, which feels like a remote island escape. You’ll cross a shallow lagoon (yes, you’ll get a little wet!) to reach a wide, peaceful shoreline filled with shells and nesting birds.
If you’re feeling adventurous, book an eco-tour or jet ski dolphin tour to explore nearby mangroves and islands.
Dinner: Snook Inn (Marco Island)
Dine on the water at this iconic island restaurant. Fresh grouper, frozen drinks, and live music — need we say more?
Where to Stay in Southwest Florida
You can stay in one central spot and do day trips, or pick a different hotel for each region. Here are a few options:
Fort Myers: Luminary Hotel (Downtown), Pink Shell Beach Resort
Naples: Inn on Fifth, Naples Grande Beach Resort
Sarasota: Art Ovation Hotel, Lido Beach Resort
Final Thoughts
Southwest Florida offers a perfect mix of relaxation, adventure, and charm, with some of the most beautiful beaches in the state.
Whether you’re strolling Naples Pier, kayaking through mangroves, or watching the sunset on Siesta Key, this 3-day itinerary gives you a taste of everything this coast has to offer.
Pack your sunscreen, bring your camera, and get ready for one unforgettable Florida escape. 😎
👉 Planning a longer Florida trip?Check out our Florida Road Trip Guide for more itineraries and travel tips!
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Booking a last-minute trip to Florida?
If so, we have you covered. Here are some top recommended tours and experiences!
Top Tours in Florida – Viator
Top Hotels In Florida – Booking.com
Looking To Get Around In Florida?
Check out rental car rates here! 🚗
