Florida Gulf Coast Travel Guide: Road Trip Itinerary

By | Wine & Travel Writer
Last Updated: September 5, 2023
Florida Gulf Coast Road Trip Itinerary & Travel Guide • Winetraveler

Florida Gulf Coast Road Trip Itinerary

Florida’s Southwest Gulf Coast may not be the part of the state that most travelers think about when planning a vacation to Florida, but it’s this fact that makes it one of the state’s most beautiful hidden gems. Between Naples, FL and the Tampa Bay area, travelers can find pristine white sand beaches, barrier islands that boast some of the best sunsets in the world, and plenty of places to wine & dine in true Florida style.

When planning your next Florida vacation, consider Southwest Florida, and check out some of these culinary & cultural spots along the way.

Florida Gulf Coast Vacation Ideas

Naples/Marco Island

At the southern end of this Southwest Florida itinerary is Marco Island and the city of Naples, FL. For context, Naples is about an hour and a half drive west across the state from Miami, or a two-and-a-half-hour drive south from Tampa. However, there are airports located in Southwest Florida that you can fly into and stay local to this area such as Naples Airport and Southwest Florida International Airport located closer to Ft. Myers. You can search for flight deals into Florida here.

Naples and Marco Island are both known for beautiful, easily accessible beaches and abundant golf courses, but these aren’t the only draws to this part of the state. The 5th Avenue South neighborhood of Naples is home to plenty of high-end shopping and dining along a sophisticated and lush tropical promenade. With just a casual stroll down 5th Avenue, a wine traveler will notice many cafes, restaurants, and bars to stop for a coffee and gelato, glass of wine, or a delicious meal. Perhaps the best part of the stroll is that it runs into the Gulf of Mexico at Naples’ beach.

Hobnob Kitchen and Bar is a neighborhood favorite with trendy American bistro dishes such as scallop ceviche, octopus appetizers, ample seafood dishes, soups & salads, prime meats, and more! The wine list leans California, but there is something for every dish. It’s a chic but relaxed spot along the Avenue.

If something more casual is what you had in mind, Marco Island south of Naples offers lots of options for waterside dining. CJs on the Bay is a popular sunset-watching cocktail spot. Menu items skew coastal casual with a wide array of options from coconut shrimp to seafood linguini. Check out their daily cocktail specials and leave your wine snob hat at home. It might be more refreshing to sip a Margarita or fruity Daiquiri and enjoy the views at this relaxed waterfront restaurant.

When it comes to lodging, there are many options from glamourous to ticky-tacky depending on your beachy needs. Some of the bigger resorts in the Marco Island area include the luxurious JW Marriott Marco Island Beach Resort, which is known for its incredible gulf views and several onsite restaurants that include a range of culinary creations from fine dining to tiki hut beachside bars. Alternatively, you can stay at an all-inclusive resort like the The Ritz-Carlton in Naples.

Further north, the Inn on 5th in Naples is a boutique hotel that sits right on the action of 5th Avenue, close to the picturesque Gulf beaches. Easily walkable to dining and attractions in the South Naples area as well as just a short drive to Southwest Florida’s famous golf courses and other attractions.

Southwest Florida Nature

For nature enthusiasts, there is plenty to do and see within a few miles of the Naples area. Just 30 minutes east of Naples is the Corkscrew Swamp Sanctuary and Blair Audubon Center*. Stroll a 2.5-mile boardwalk system through natural Everglades and see how Florida’s stunning and sometimes scary flora and fauna exist outside of development. This is a must-see for bird watchers and wild animal enthusiasts.

Just north of Naples is the Everglades Wonder Gardens* in Bonita Springs. A perfect stop for the whole family, the Everglades Wonder Gardens is home to alligators, turtles, Flamingos, parrots, and more. Tours are available, but it’s always best to check the website to see when the park is open.

Florida Vacation Ideas: Sanibel Island
Sanibel Island is known for its world-class shell hunting opportunities.

Ft. Myers/Sanibel & Captiva Islands/Boca Grande

About 45 minutes to an hour north of Naples is the Ft. Myers area, which is also home to the barrier islands of Sanibel, Captiva, Gasparilla Island and many more, recognized as some of the premier island escapes in all of Florida.

Head out to Sanibel and Captiva Islands for prime sunset real estate. If you haven’t experienced a Florida Gulf Coast Sunset, put it on your bucket list! Sanibel and Captiva are both excellent locations for those who love “old Florida” beaches and nature parks. A drive through these islands will take you back to the simple life, and that’s exactly what they offer: an escape from the chaos of the mainland.

RELATED: Romantic Getaway: Wine Tasting & Shell Hunting on Sanibel Island

There are several casual dining spots on the islands with fresh seafood and Key Lime pie being menu staples. Rumrunners are the drink of choice for island dwellers, so don’t expect a fancy wine list at most spots. When life gets too crazy, Sanibel and Captiva Islands offer the perfect excuse to sit back, relax, and enjoy the peace that comes with watching the waves roll on the shore.

If you’re looking for “old Florida” lodging during your stay in the Ft. Myers area, check out Tarpon Lodge in Bookelia, Florida. Tarpon Lodge offers accommodations in their 1926 historic lodge building, as well as a private cottage, boathouse, and the more modern Island House. There’s also a four-star dining experience waiting at the Tarpon Lodge restaurant on site.

For those who really want to get off the beaten path, or who enjoy an escape where there are no beaten paths, visit Cabbage Key, Tarpon Lodge’s sister property, only accessible by boat. There are no paved roads on the island, just tropical landscapes, an inn, cottages, bar, and a restaurant that sees daily boaters who stop by for a refreshment and meal.

Boca Grande is a tiny village located on Gasparilla Island, between Charlotte Harbor and the Gulf of Mexico, that has been the winter home of many famous folks throughout history. Gasparilla Island is named for the pirate, José Gaspar, who may or may not have been a work of fiction. However, it is undisputed that pirates roamed this area as recently as the 1770s.

This area is known as the tarpon fishing capital of the world, and the history of maritime commerce is fascinating, so be sure to read up on the past while you’re here.

Once in Boca Grande, you must check out or stay at the historic Gasparilla Inn, a beautifully restored hotel that opened in 1913. Dine nearby at The Pink Elephant, a charming restaurant serving guests for over 60 years that has been awarded the Wine Spectator Award of Excellence every year since 2012. Diners can enjoy a casual lunch downstairs or on the patio with refreshing cocktails, salads, and sandwiches, or make a reservation for dinner upstairs in the more formal dining room. Travelers arriving by boat even have dockage space for easy access to the restaurant by water.

Spending time on these barrier islands is truly an escape to a bygone paradise on Florida’s southwest gulf coast.

Sarasota/Siesta Key/Longboat Key & Anna Maria Island

Welcome to Florida’s Sun Coast and the slice of the state that boasts the best beach in the country! Imagine sinking your toes into baby powder-soft white sand that is always cool to the touch, no matter the time of day or season. Siesta Key is a barrier island off of Sarasota, which is about an hour south of Tampa Bay, and it has been ranked 2020’s #1 Beach in the U.S. by TripAdvisor’s Traveler’s Choice Awards™. Siesta Key and the whole Sarasota area is a boating and beach-lover’s paradise. But the fun doesn’t stop at the shoreline! Sarasota and Manatee Counties are home to culinary and cultural delights from Sarasota’s bayside downtown to the several islands that outline the coast from the almost exclusively private Casey Key to Anna Maria Island that jets into Tampa Bay. Let’s dive into a few spots throughout this part of Florida’s Gulf Coast.

Casey Key

If you’re into bike riding, Casey Key is a beautiful spot in the world to explore on two wheels. Large private homes and a stunning coastline that hugs the road makes Casey Key feel more like an island in your dreams, or a picture-perfect page out of a Mediterranean magazine. It’s home to several small motels, but most overnight accommodations are found on the mainland, or further north in Siesta Key. Casey Key is only accessible to the mainland by two bridges, one on the south end of the island near the city of Venice, Florida, and one on the northern end of the island, known as the historic Blackburn Point Bridge, which is a swing bridge that was opened in 1926 and still swings to this day.

All Casey Key visitors should stop for lunch or dinner at the Casey Key Fish House right past the Blackburn Point Bridge. Easy-going and “keysy,” this island seafood restaurant offers fish house classics and a tropical tiki bar for totally casual dining. If you have access to a boat, simply pull it right up to the dock, and hop-off for easy dockside parking.

RELATED: 18 Incredible Places To Have a Glass of Wine in Miami

Siesta Key

Siesta Key is Florida at its best. Between the number one ranked beach in the country and the popular Siesta Key Village with shops and restaurants to fit any desire, there is really no need to leave the island once you are there. There are two ways on and off the island, and one main road that runs the length of it, but most of it can be traveled easily either on foot, bike, free ride, or trolly, which picks up in the Village and runs the length of the island with stops along the way.

Most of the coastline along Siesta Key is speckled with low rise hotels, resorts, motels, and rentals. The island is largely seasonal (a winter escape for cold Midwesterners), meaning there may be minimum stay requirements ranging from nights to weeks at many of the rentals. Although, once you’ve settled into your beachy cabin, you may never want to leave anyway.

When it comes to dining on Siesta Key, there are many options from the world-famous SKOB (Siesta Key Oyster Bar) with live music and happy hour specials daily, to the chic Summer House steak and seafood restaurant, and next door, The Cottage, with an unpretentious yet delicious menu of items like Peruvian Ceviche and cheesy gnocchi for locals and visitors, alike.

Winetraveler Tip: Don’t leave Siesta Key without visiting the beachy chic Siesta Key Wine Bar. It’s the perfect resting spot for a boat-tired wine traveler looking for a glass (or bottle) of something red, white, or rosé. Siesta Key Wine Bar offers an international selection of wines, as well as some sweet Florida favorites at retail prices with only an $8 corkage fee to drink on site.

St. Armands/Longboat Key & Anna Maria Island

Follow the islands on the coast north via downtown Sarasota to Lido and St. Armands Key up through Longboat Key & Anna Maria Island. These islands are mostly residential and hospitality-focused. St. Armands Circle is home to many small restaurants and shops and offers an afternoon full of dining and entertainment. As you drive around the circle, you will find island favorites like Tommy Bahama Restaurant & Bar and the Spanish tapas spot, Columbia restaurant, as well as locally-inspired retail, salons, and sweet shops.

Perhaps the most quintessential coastal dining is at Shore, which has a location in St. Armands Circle and further up the coast on the northern end of Longboat Key. Both Shore locations offer al-fresco dining, specialty cocktails, classic seafood and American dishes, and cool vibes. If coastal chic is your style, then you must visit the store at Shore, where you can find all the trendiest island wear and accessories.

Anna Maria Island is a Florida getaway in itself, named by the explorer, Ponce de Leon, for the queen of his benefactor, Charles II. Follow the road north where you drive by the beach on the west and adorable island bed & breakfasts, motels, and trinket shops on the other side of the road. It’s a coastal paradise where everything is casual and laid-back. Anna Maria Island offers a true remote Florida vibe across much of the island. You can take a look at some accommodation options on Anna Maria Island here.

Winetraveler Tip: If you are a coconut cake fan, don’t miss Hometown Desserts near the pier on Anna Maria Island. Buy by the slice or a whole cake! Coconut and Key Lime cakes are an island must-eat!

Downtown Sarasota

Bringing it back to the mainland, you don’t want to miss a stop in downtown Sarasota. There are many fantastic places to dine around town, you’ll need weeks to get through them all! We recommend staying in one of these upscale hotels so you can explore at a leisurely pace.

For a true rustic Florida dining experience with some of the best fresh fish in town, head over to Owen’s Fish Camp on Burns Court. The restaurant encompasses several dilapidated bungalows, but the vibe is far from ramshackle. You won’t be disappointed by the quality of your dinner, or the uniqueness of the experience. Leave your pretensions at home but order a bottle of wine from the tightly curated “wine snob” bottle list and enjoy your “so Florida” dinner.

Over near Main Street in downtown, try a locally sourced dish from atmospheric Boca, or walk around the corner for an authentic French meal at C’est La Vie. Every Winetraveler needs a local wine bar, and you get just that at Grand Cru Wine Bar right on Main Street. At Grand Cru, choose your wine and pour it yourself with their wine-on-tap system. A large beer selection is available as well with small dishes freshly prepared on-site.

For waterside dining, check out Marina Jack right on the bay, with plenty of dock space for seaside travelers who arrive by boat, or Jack Dusty at the Ritz-Carlton for a more upscale coastal lounge feel.

Winetraveler Tip: Don’t limit your dining to downtown Sarasota! Southside Village is not far from downtown and offers classic dining spots in a range of cuisines. Grab a specialty coffee or glass of wine at Perq Coffee Bar, sushi at Pacific Rim, seasonal favorites at Libby’s, or oysters at Veronica Fish & Oyster. Southside Village offers a walkable small-town feel with several great dining options.

Sarasota Area Cultural Stops*

If you’ve done all the beaching and boating you can handle, check out some of the cultural spots around the Sarasota area. On the south side of the city near downtown, stroll the Marie Selby Botanical Gardens, a 15-acre tropical plant sanctuary and museum on the bay including the former home of Marie and William Selby.

“Sarasota Modern” is an architecture style that you’ll notice around town, so it’s only right to explore structural design while you’re in town. Check out the exhibits on display at the Center for Architecture Sarasota in downtown for more on what makes this city so stylish.

Further north is the John and Mable Ringling Museum of Art (“The Ringling”), which is the official state art museum for Florida. It was established in 1927 and is now run by Florida State University. The museum consists of more than 10,000 items across many exhibits. It is part of the 66-acre Ringling Estate that includes the Ca’d’Zan, which was the Venetian Gothic-style mansion and home of John and Mable Ringling completed in 1926, Mable’s Rose Garden, built in 1913, the Circus Museum, Ringling Art Library, and the FSU Center for the Performing Arts.

*Cultural attractions may be closed or running on limited hours due to COVID-19. Check each website for more information on daily changes.

Best Things To Do in Tampa Florida

Tampa Bay

Tampa Bay is a large area that includes several cities and neighborhoods from Tampa on the east side of the bay to St. Petersburg on the peninsula on the Gulf of Mexico accessible by the infamous Sunshine Skyway Bridge, which is worth the drive over to revel in the engineering marvel of it all. The actual Tampa Bay is a shallow estuary that is 400 square miles in size, meaning this is not just one place to see.

For the purposes of this itinerary, we will pick a couple of places to highlight on your Southwest Florida road trip through the Tampa Bay area.

St. Pete

Downtown St. Pete is a great place to park the car and walk around to explore the many shops and restaurants along tree-lined Beach Drive. Perhaps the greatest attraction here is the new St. Pete Pier that opened in the summer of 2020. The pier is home to quite a few different restaurants and attractions that can be enjoyed by the whole family.

There are several restaurants leading up to the pier itself, such as regional favorite, Doc Ford’s Rum Bar & Grille, for the rum enthusiast, and Fresco’s Waterfront Bistro for outdoor seating on the water. However, the spots located inside the actual pier are the main attraction.

Teak is a fine dining restaurant with complete views of the pier, St. Pete, and surrounding Tampa Bay. The bar at Teak overlooks the Bay, and visitors who stop for an Aperol Spritz during the hot afternoons can enjoy watching boats coming and going underneath, while small airplanes take off from the nearby airport and circle overhead.

If rooftop views bring you delight, head to the top of the pier and grab a drink at Pier Teaki, a modern take on a casual tiki bar located on the highest level of the pier with unobstructed views of the surrounding area. Pier Teaki is open late night for nighttime revelers.

Winetraveler Tip: Not feeling like dealing with crowds at the pier? Check out Bacchus Wine Bar in downtown St. Pete. Small & quaint with lots of light, this wine bar has a menu with all of your favorite French bites and bottles from around the world. Worth a stop for a glass during your time in St. Pete.

St. Pete Beach

On the west side of the peninsula on the gulf coast is St. Pete Beach. A neighborhood in itself where visitors can stay in one of the many beach resorts ranging from upscale to economical. Lots of places to choose from make this a traveler’s beach paradise.

Downtown Tampa

Just like a lot of cities around the country, Tampa has been growing quite a bit over the last few years and adding numerous cool spots to explore. This growth has allowed for new restaurants and attractions to pop up all over the downtown area. Two main destinations bookend the downtown river boardwalk, and there are several accommodation options not far from the area.

Armature Works is a mixed-use building in the Tampa Heights neighborhood, right on the Hillsborough River. It resembles a food hall, public market, and more! The vibe is industrial chic with dining options for every taste bud.

On-site, you can have a glass of wine from Cru Wine Bar, located on the main level,  or head upstairs to the rooftop bar, M. Bird, for a classy cocktail while you watch the sunset over the Hillsborough River.

Throughout the Armature Works area, there is plenty of outdoor space and seating for people watching and family playtime. It’s a destination worth a day or full evening visit for eating, drinking, and hanging out in Tampa.

Next door to Armature works is Ulele, a “Florida”-style restaurant with a rustic-chic vibe and large menu with many seafood favorites. Great for dates or a special occasion, even if the occasion is a regular Tuesday night.

On the other side of downtown Tampa is Sparkman Wharf, another outdoor dining destination with many options for food, drinks, and entertainment. Sparkman Wharf has a dining garden full of containers of Tampa’s top culinary talent trying new concepts alongside craft brewers. It’s a relaxed place to grab a plate of something new, a craft beer, and hang out by the river.

No trip to Tampa would be complete for Winetravelers without a visit to Bern’s Steakhouse. Bern’s is one of the most famous steakhouses and boasts one of the largest wine collections in the world. Come with an open mind and adventurous palate, and let the sommelier choose bottles for you based on your price range. Don’t skip on dessert, as Bern’s is well-known for its sensual Harry Waugh dessert room, where enjoying a sweet treat is an entire experience in itself.

This itinerary is by no means an exhaustive list. There are many hidden gems along Florida’s southwest Gulf Coast. Start with some of these ideas and run with it! Explore & discover! The options for entertainment, dining, and adventure are endless.

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