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6-Day Florida Gulf Coast Road Trip Itinerary: Beaches, Seafood, and Sunsets

By Jeff Lowe • January 7, 2026

6-Day Florida Gulf Coast Road Trip Itinerary: Beaches, Seafood, and Sunsets

Florida’s Gulf Coast is tailor-made for a road trip. Distances are manageable, the scenery changes just enough to keep things interesting, and the rhythm of the coast encourages you to slow down and enjoy the moment.

Warm Gulf waters, soft white sand, and nightly sunsets over open water give this side of Florida a completely different feel from the Atlantic coast. It’s less hurried, more laid-back, and incredibly easy to love.

We’ve traveled Florida’s Gulf side many times over the years and keep coming back for the same reasons: calm water you can actually relax in, beaches that feel made for long walks, and sunsets that somehow never get old.

This six-day Florida Gulf Coast road trip strings together some of the most enjoyable coastal stops, balancing beach time, seafood, and just enough variety to make each day feel distinct. It’s not about rushing — it’s about settling into the Gulf Coast mindset and letting the days unfold naturally.

Day 1: Tampa and St. Petersburg to Clearwater Beach

Most Gulf Coast road trips start in the Tampa Bay area, and it’s a great place to ease into the journey. Tampa itself has plenty going on, but we’ve always found it works best as a launching point — pick up your car, grab a meal, and head toward the water.

Clearwater Beach is an easy first stop and sets the tone for what’s ahead. The sand here is bright and powdery, the beach is wide, and the water stays shallow and warm. After travel, it’s the kind of place where you can kick off your shoes and instantly feel like vacation has begun.

One of Clearwater’s standout traditions is the nightly sunset celebration at Pier 60. As the sun drops into the Gulf, musicians and street performers gather along the pier. It’s casual, friendly, and feels very “Florida” in the best way.

Don’t Miss

  • Walking the length of Clearwater Beach in the early evening

  • Pier 60 at sunset

  • Fresh grouper sandwiches or shrimp baskets at a beachfront restaurant

Local Tip
If you arrive early enough, spend a little time on the beach before dinner. The first Gulf Coast sunset of a trip always seems to set the mood for everything that follows.

Day 2: Clearwater to Anna Maria Island

The drive south toward Anna Maria Island is short but scenic, hugging the coast and passing smaller beach towns along the way. Anna Maria Island feels like a step back in time — low-rise buildings, pastel beach cottages, and streets where bikes and golf carts are the norm.

This is one of those places where you don’t need much of a plan. Choose a beach access, spread out a towel, and let the day slow down. Bean Point, at the island’s northern tip, offers sweeping views of the Gulf and Tampa Bay, while Coquina Beach on the southern end feels more spacious and relaxed.

We’ve always appreciated how Anna Maria manages to stay low-key despite its popularity. It’s ideal for travelers who want a quieter beach day without sacrificing beauty.

Best Beaches

  • Bean Point for wide-open views

  • Coquina Beach for space and shade

  • Manatee Public Beach for easy access and amenities

Sunset Spot

  • Anywhere on the west-facing shoreline — sunsets here are consistently excellent

Day 3: Anna Maria Island and Sarasota, Including Siesta Key

From Anna Maria Island, head south toward Sarasota, where the beaches take on a slightly different character. Siesta Key is the star here, known for its incredibly fine, cool-to-the-touch sand. Even after visiting many Gulf Coast beaches, this one stands out.

Siesta Key Beach is large enough that it never feels too crowded, and the calm Gulf water makes it perfect for floating, wading, or just sitting at the shoreline watching the waves roll in. It’s an easy place to lose track of time.

Later in the day, Sarasota offers more dining options and a bit of cultural flavor. St. Armands Circle is a pleasant place to stroll, shop, and grab dinner before heading back toward the beach for sunset.

Things to Do

  • Spend the afternoon at Siesta Key Beach

  • Walk St. Armands Circle

  • Enjoy a sunset walk along the shoreline

Food Note
This stretch of the coast does seafood especially well, but it’s also a good place to mix in something different if you’re craving variety.

Day 4: Sarasota, Venice, and Naples

This day introduces a few subtle changes in scenery as you continue south. Venice Beach makes for a great morning stop. It’s famous for shark tooth hunting, and even if that’s not your thing, the beach itself is quiet and uncrowded.

From Venice, continue toward Naples, where the Gulf Coast starts to feel a little more polished. Naples beaches are clean, wide, and well maintained, and the town itself offers a blend of casual and upscale dining.

Naples Pier is a must-stop in the evening. It’s one of those classic Gulf Coast spots where locals and visitors gather to watch the sun disappear into the water. Dolphins often swim nearby, and the atmosphere is relaxed and welcoming.

Don’t Miss

  • Morning beach walk in Venice

  • Naples Pier at sunset

  • Waterfront dining in Naples

Driving Tip
Traffic can pick up in Naples during peak season, so give yourself extra time and lean into the slower pace.

Day 5: Naples and the Fort Myers Area, Including Sanibel and Captiva

This part of the Gulf Coast has always been one of our favorites. The Fort Myers area strikes a nice balance between developed beach towns and more natural island settings. The drive toward Sanibel and Captiva is scenic, crossing causeways with water views that immediately signal you’ve arrived somewhere special.

Sanibel Island is known for shelling, and for good reason. A simple morning walk along the beach often turns into a small treasure hunt. The island itself is relaxed and easygoing, with bike paths and plenty of quiet corners.

Nearby Captiva Island adds a splash of color and charm, with small resorts, beach bars, and some of the most memorable sunset views on the coast.

Best Experiences

  • Shelling along Sanibel’s beaches

  • Biking or driving slowly through the island

  • Sunset dinner overlooking the Gulf

Sunset Tip
This stretch of coast consistently delivers dramatic sunsets — give yourself time to sit, watch, and enjoy the show rather than rushing off to the next stop.

Day 6: A Slow Morning and Flexible Return

The final day is best kept intentionally light. Enjoy a slow breakfast, take one last walk on the beach, and soak in the final views of the Gulf. Depending on your schedule, you can either begin the drive back toward Tampa or consider extending the trip with an overnight stay or side excursion.

Some travelers opt to detour toward natural areas inland, while others prefer to squeeze in one more beach stop before heading home. Either approach works — the beauty of this road trip is its flexibility.

Ideas for Extending the Trip

  • Add extra nights in the Fort Myers area

  • Explore smaller beach towns you passed along the way

  • Slow the pace and spend two nights in favorite spots

Best Time of Year for a Florida Gulf Coast Road Trip

One of the advantages of Florida’s Gulf Coast is its long travel season. Late fall and spring tend to offer the best balance of warm water, comfortable temperatures, and fewer crowds. Winter brings cooler evenings but still plenty of sunny days, while summer offers the warmest water — though with higher humidity.

From our experience, shoulder seasons provide that sweet spot where everything feels relaxed without sacrificing beach weather.

Where to Stay Along the Route

Accommodations along the Gulf Coast range from beachfront resorts to cozy vacation rentals.

Good Options Include

  • Beachfront condos for space and sunset views

  • Small coastal inns for charm and walkability

  • Resorts for amenities and convenience

Staying near the beach often makes evenings more enjoyable, especially when sunsets are part of the daily routine.

Seafood You’ll Find Along the Way

Seafood is a constant companion on this road trip, and that’s part of the fun. Menus change slightly as you move south, but expect plenty of:

  • Grouper sandwiches

  • Gulf shrimp

  • Fresh fish tacos

  • Blackened or grilled catch-of-the-day specials

Keeping meals casual most nights fits the relaxed Gulf Coast vibe perfectly.

Why This Road Trip Works So Well

What we love most about the Florida Gulf Coast is how easy it is to enjoy. The water stays warm, the beaches invite long, unhurried days, and sunsets give each evening a natural sense of closure. Every stop along this route offers its own personality, yet the overall experience feels cohesive and calm.

If you’re looking for a road trip that doesn’t require constant planning or early mornings, this one delivers. It’s about finding a beach chair, enjoying a great meal, and watching the sun sink into the Gulf — day after day.

Final Thoughts

A six-day Florida Gulf Coast road trip offers exactly what many travelers are looking for: beautiful beaches, memorable meals, and a pace that encourages you to slow down and savor the journey.

With warm water, welcoming towns, and sunsets that never disappoint, it’s no surprise this stretch of coast keeps calling us back. Whether it’s your first visit or one of many, the Gulf Coast always finds a way to feel familiar and special at the same time.