23+ Memorable Stops For a Perfect West Coast of Florida Road Trip

There are so many amazing things to do in Florida that planning a trip to the Sunshine State can be overwhelming. Our cure? An old-fashioned road trip to hit the highlights on the Gulf Coast!

We’ve put together this itinerary for the west coast of Florida that is sure to make you smile.  So rent a convertible, put the top down, and let’s get ready to explore the beauty of our southern neighbor.

23+ Memorable Stops For a Perfect West Coast of Florida Road Trip
Sunset at the Island Inn Sanibel Island

Tampa Bay

In Tampa Bay you’ll find a sparkling waterfront, world-class chefs, family fun, and a century of Cuban culture!

Things to Do in Tampa

Rent two bikes from a bike share location and tool along the Riverwalk, or if you’d rather view downtown FROM the water, book a kayak or stand up paddleboard from Urban Kai

TIP: For thrill seekers, nearby Busch Gardens has the largest number of roller coasters in Florida. The Tigris coaster runs backward and forwards and turns upside down at 60 mph. Our friends at Trekaroo have the scoop on the best things to do in Tampa Bay with Kids

Where to Eat

The Tampa Riverwalk is bookended by two new food halls, Heights Public Market – Amature Works (once a trolley barn) and Sparkman Wharf (made of shipping containers). Because you’re in Tampa, you need a Cuban while you’re here! The award-winning Cuban from Hemingway’s at the Armature Works is a no brainer.

Where to Stay

The hip Aloft Tampa is right on the waterfront with a pool that overlooks the river. Plan your trip at the right time and you can meet local artists in the lobby.

TIP: On a rainy day you can still get in a round at Topgolf. Take a break and try the buffalo cauliflower and the injectable donut holes (or fun with food as I like to call them).

Skip the grab-and-go breakfast and head across the bridge to Oxford Exchange, one of Tampa’s most Instagram-able spots (and breakfast to die for).

Clearwater Beach

Clearwater Beach not only features impeccable beaches and inviting waters, but also an inviting, small-town atmosphere.

Things to Do in Clearwater

Have your name engraved on a grain of rice, then clap along with the buskers as they perform feats of amazing proportions. You can do it all nightly at Pier 60 as you watch the sunset on the beach.

Afterward, take a moonlit dip in the blue-green waters of the Gulf of Mexico.

TIP: You can visit Winter from the movie Dolphin Tales at the Clearwater Aquarium!

Where to Eat

When in Clearwater, at least one meal needs to be at Frenchy’s Rockaway Grill, located right on the beach. Grab a seat at the rail for sunset, order a rum-runner and the garlic crab fries while you listen to live music.

Where to Stay

The Wyndham Grand at Clearwater Beach is a perfect home base right on the beach. There is much to love about this hotel, but our favorite was dinner at Ocean Hai. We ordered the Kaiseki, the chef’s tasting menu.

My teen son and I both enjoyed this culinary experience that was truly beyond words. We slowed down. We tried new things, talked non-stop in-between courses about school, friends, sunburn and what might come out next. The dishes were beautifully presented and delicious. The entire experience made dinner an event we are still talking about.

23+ Memorable Stops For a Perfect West Coast of Florida Road Trip
Part of the Chihuly exhibit at the Morean Arts Center in St. Pete.

St. Petersburg

In St. Petersburg you’ll find award-winning beaches, awesome museums, and plenty of outdoor fun.

Things To Do in St. Petersburg

There is much to Instagram in St. Pete, be sure to have your phone charged. Don’t miss the Avant-Garden at the Dali Museum with its melting clocks, mustached birds and wishing tree!

The Dale Chihuly permanent collection at the Morean Arts Center is as wonderful as you’d expect. Plan your visit ahead of time and book a glass blowing workshop afterward, or just watch the glass-making demonstration.

On our list for next time is a walking tour of downtown murals with Florida CraftArt and a visit to St. Pete Beach.  

Where to Eat in St. Petersburg

Bodega on Central is a little Latin American-inspired street side café with outdoor seating. You can’t go wrong with any sandwich or plate, but make sure you also get a side of jicama slaw. Seriously, it’s To. Die. For.

23+ Memorable Stops For a Perfect West Coast of Florida Road Trip
Lido Key, Sarasota


Sarasota — the culture capital of Florida — is also home to great beaches, amazing restaurants, and awesome shopping.

Things To Do In Sarasota

There is so much to do in Sarasota you’ll likely need a few days, but if you only have one, spend the day on Lido Key. The beach here was once for whites only, but in the 50’s and 60’s residents of nearby Newtown staged a wade-in at the beach. You can hear all about it and the other ways African American residents in Sarasota contributed to the Civil Rights movement with a tour from Newtown Alive!

TIP: Looking for a more laid-back beach vibe? Two of the most popular beaches near Sarasota are Siesta Key and Anna Maria Island. And if you have your four-legged family member with you, find out which beaches are dog-friendly here!

Where To Stay In Sarasota

Although you’ll be out at the beach during the day, stay in Downtown Sarasota at the Art Ovation Hotel, one of the coolest hotels I’ve ever visited. The rooftop pool and bar offers a fantastic view of the city, and the location is walking distance to shops, art galleries, and several theatres.

Where To Eat In Sarasota

If you stay at Art Ovation, you’ll also be a few blocks from Sage, located in an historic building that once housed the local newspaper. Put your name in for the restaurant before heading up to the rooftop bar. Everything is excellent at Sage, so go hungry.

23+ Memorable Stops For a Perfect West Coast of Florida Road Trip
The patio of Snook Haven in Venice Florida


You’ll find 14 miles of white-sand beaches from Casey Key to Manasota Key and plenty of recreational opportunities in Venice.

Things To Do In Venice, Florida

If the season is right, catch an Atlanta Braves spring training game at CoolToday Park. Take a walk around the field, grab a beer at the Tomahawk Tiki Bar, watch kids roll down the grassy hill at Coca-Cola Corner. Stroll further and see the pitchers practicing just below you.

If it isn’t baseball season, discover the 15 miles of trails at the urban oasis that is Oscar Scherer State Park. Oscar Scherer is a little quieter than nearby (and better known) Myyaka River State Park.

Where To Stay In Venice, Florida

There aren’t many hotels (yet) near the Braves CoolToday Field because it just opened in 2019. However, we stayed at the Home2Suite Hilton in nearby Nokomis, which was very close to downtown Venice, one of the cutest small towns in Florida.

Where To Eat In Venice, Florida

Head down a dirt road to Snook Haven, a restaurant where you’ll find BBQ, live music and boat tours of the Myyaka River.

For something a little less casual, venture to Venice’s adorable and historic downtown to Made in Italy. The homemade pasta dishes are out of this world.

23+ Memorable Stops For a Perfect West Coast of Florida Road Trip
Thomas Edison’s office looks just as it did when he was working in his lab at his winter estate.

Fort Myers

Beaches, fishing, and shopping are just some of the fun things to do in Fort Myers.

What To Do In Fort Myers

The palm tree-lined McGregor Blvd in Fort Myers is the perfect place to ride with the top down. Your destination is the Edison and Ford Winter Estate.

Thomas Edison was a die-hard baseball fan and you can find pictures of him with the Oakland A’s in the museum. If you’re a true baseball fan, plan to visit during the annual vintage baseball weekend.

TIP: For a fun detour, take the Key West Express from Fort Myers to Key West for a day or two, then resume your road trip!

Where To Eat In Fort Myers

Along the beautiful McGregor Avenue is the shaded patio of the McGregor Café. Your order: Lobster cake salad with an ice tea in a Mason jar, and Key lime pie for dessert. You can thank me later!

23+ Memorable Stops For a Perfect West Coast of Florida Road Trip
Kayaking through the mangroves of the Commodore Creek Trail of Tarpon Bay.

Sanibel and Captiva Island

Just a short drive from Fort Myers, you’ll find Sanibel Island — the perfect place for sunset-watching and shelling.

What To Do In Sanibel Island

We love Florida’s west coast beaches, especially Sanibel Island. One of the best things about Sanibel and nearby Captiva Island is that it isn’t one of those overdeveloped beach towns, but there are still tons of things to do.

Our favorite? Kayaking the mangroves of Tarpon Bay. The Bay is one of the top ten places in the nation to paddle according to Canoe and Kayak Magazine. Rent a kayak through Tarpon Bay Explorers and head out on your own, or go on a guided tour.

Either way, you’ll have a front row seat to one of the most diverse and productive ecosystems in the world.

Where To Eat In Sanibel Island

For a casual lunch, head to local favorite Doc Ford’s for some Yucatan shrimp tacos.

For an elegant dinner, try the newly renovated Old Captiva House for blackened snapper, and for dessert, the Bubble Room on Captiva Island for orange crunch cake.

Where To Stay In Sanibel Island

The Island Inn is located right on the beach and has five different hotel room types, as well as cottages — so no matter your group size, they have you covered. The best part of our cottage was a huge screened porch and plenty of room to spread out. Make sure you sign up for the beach walk led by a scientist from the Bailey Matthews National Shell Museum.

Not ready for your road trip to end? We have exactly what you need to know to travel to South Florida too.  West Palm Beach, Fort Lauderdale, and Miami are calling your name!

And if you’d rather just hit the Florida Beaches, we have you covered there too. Our list includes some of the west coast Gulf beaches, and east coast Atlantic beaches — so no matter which side of the state you’re visiting, we’ve got some great spots.

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23+ Memorable Stops For a Perfect West Coast of Florida Road Trip

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