If you’re looking for a weekend that blends old-school charm, powdery white sands, and sunset cocktails, this is it.
This 3-day Gulf Coast road trip takes you from the sponge docks of Tarpon Springs to Bridge Street in Anna Maria Island, hitting all the beachy highlights in between.
Whether you’re after baklava by the bay, a grouper sandwich at the beach, or just a quiet moment with your toes in the sand, this itinerary is your perfect mix of adventure and chill.
Let’s dive in!
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Day 1: Tarpon Springs + Clearwater Beach
Morning: Explore Tarpon Springs (Greek Town Vibes)
Start your trip in Tarpon Springs, known for its sponge docks and rich Greek heritage.
Wander through quaint shops, grab a coffee by the water, and don’t leave without trying authentic baklava or a gyro from Hellas Restaurant.
My favorite part of Tarpon Springs was definitely the baklava. It’s great if you’re looking for a sweet treat.
Don’t miss:
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The Sponge Docks
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Greek bakeries & cafes
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Sunset cruise if you’re staying overnight
Afternoon: Clearwater Beach
From Tarpon, it’s just a 30-minute drive to the award-winning sands of Clearwater Beach.
It’s more lively and touristy but worth the buzz—perfect for swimming, jet skiing, and people-watching.
Quick eats: Frenchy’s Rockaway Grill (try the grouper sandwich or baked oysters) or Palm Pavilion next door. Palm Pavilion is my new oceanfront favorite with great prices.
Pro tip: Stay until sunset at Pier 60 for live performers and golden hour photos.
Day 2: Pass-a-Grille + St. Pete Beach + Treasure Island
Morning: Pass-a-Grille (Old Florida Feel)
Head south to the charming, lesser-known Pass-a-Grille, where beach cottages line quiet streets and the vibe is pure relaxation.
Walk the white sand beach, explore quirky shops, and grab food by the water at Paradise Grille or Brass Monkey.
Why go: It’s quiet, walkable, and feels like a step back in time.
Afternoon: St. Pete Beach
Just a few minutes away, St. Pete Beach offers a bit more energy with water sports, resorts, and bars.
Don’t forget to snap a photo of the iconic pink Don CeSar Hotel.
Bonus: If you love art or want a break from the beach, pop into the nearby Salvador Dalí Museum in downtown St. Pete.
Evening: Treasure Island
Wrap up your day in Treasure Island, a wide, flat beach that’s perfect for sunset strolls.
Catch live music at Caddy’s on the Beach or sip a cold drink with your toes in the sand.
Optional overnight here for affordable beach hotels and quieter crowds.
Day 3: Anna Maria Island + Bradenton Beach
Morning: Anna Maria Island (Chill Paradise)
Drive about an hour south to Anna Maria Island, one of Florida’s most beloved beach towns.
It’s calm, clean, and full of beautiful homes, art galleries, and laid-back locals riding around in golf carts.
Must-do:
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Walk the Bridge Street Pier
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Grab brunch at the Sandbar Restaurant
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Rent a bike or paddleboard
Afternoon: Bradenton Beach
As you make your way back north or continue south, stop in Bradenton Beach for one last dose of sun and surf.
It’s a smaller, quieter spot to wind down with a final swim and seafood lunch.
Eat here: The Beach House Restaurant (beachfront dining with fresh, local ingredients).
I also love Gulf Drive Cafe with good food on the beach and oceanfront views.
Beach Town Hopping Tips:
Travel light: You’ll be parking and walking often—pack a beach bag with the essentials.
Go during shoulder season (spring or fall) for fewer crowds.
Book accommodations in two spots: one night up north (Tarpon/Clearwater), one night farther south (Treasure Island or AMI).
Final Thoughts
If you’ve been dreaming of a weekend that’s equal parts adventure and relaxation, beach town hopping along Florida’s Gulf Coast delivers.
From Greek food in Tarpon Springs to sunsets in Treasure Island to paddleboarding in Anna Maria Island, this trip is Florida at its finest—without the theme park lines or crowded mega-resorts.
Safe travels!
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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! 🚗
