Best Cities to Visit While on a Road Trip in Florida

Florida is commonly known as the Sunshine State. It is a popular destination year round due to its’ warm/hot climate. The best getaways in Florida usually involve some type of beach setting; however, there are also great inland city options too. From a Florida Keys road trip to a visit to Orlando’s amusement parks, there should be numerous stops on your Florida itinerary. If you are going on a Florida road trip, here are some of the best cities to visit in Florida.

Florida Road Trip

Gulf Coast

Marco Island

Marco Island is our family’s favorite beach getaway destination, and one of the best cities in Florida to visit. Located on the Gulf of Mexico, it is often overlooked by its neighbor Naples. Marco Island is a great place for some beach fun, great seafood restaurants, and a laid back vacation.

We love to splurge on our hotel stay at the Marriott Crystal Shores, a resort with three pools, spacious rooms, kids activities, and on-site dining. Besides spending time on the beach, check out some other ways of exploring Marco Island.

Marriott Crystal Shores

Check out: Places to Stay in Marco Island

Naples

Naples, Florida is a natural and cultural gem in Southwest Florida otherwise known as the Paradise Coast. Naples is located on the turquoise waters of the Gulf of Mexico, only a 40-minute drive from Fort Myers Airport, where you will find some of the best white sand beaches. Naples is a great getaway for both couples and families, especially if you are looking for a warm-weather getaway.  There are many activities you can enjoy such as visiting Delnor-Wiggins Pass State Park, Naples Pier the popular fishing and dolphin-spotting destination, Naples Botanical Garden, Clam Pass Beach Park, Corkscrew Swamp Sanctuary, Naples Zoo and many more.

Fifth Avenue South and Third Street South are the focal points of Old Naples where there is no shortage of shopping, galleries and of course restaurants.  Some of the local favorites are the premier brunch location, Jane’s Café, where you can enjoy an all-day breakfast menu (I highly recommend the lobster eggs Benedict), the local Tommy Bahama Restaurant has a great menu offering with an island vibe feel (I recommend the pineapple crème brulee for dessert) and be sure to visit, Café & Bar Lurcat, where you will find a great happy hour menu of $5 selections and you can’t leave without trying their famous warm cinnamon sugar donuts.

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Naples

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Sanibel

Sanibel Island has all the things cities have to offer, surrounded by breathtaking nature. Located on the Gulf Coast side of Florida, this destination is ideal for families and travelers who like to take it easy. You can enjoy a waterside bungalow, stroll through town for ice cream and discover live music at night (like George and Windy’s Corner Grill). There are some nearby natural wonders too, including the Ding Darling National Wildlife Refuge that’s perfect for kayaking and spotting manatees among the mangroves.

There are big-city amenities too for more relaxation. I love a stop at the Kay Kasperson spa for an indulgent afternoon of facials and manicures. I also can’t miss a meal at The Crow’s Nest for stone crab in season and a cocktail.

If you’re really hankering for something livelier and more city-like, you can head across the bay to Fort Myers. There’s plenty of fun nightclubs, bars, and restaurants to enjoy over the bridge too.

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Sarasota

Whether visiting for the world-renowned art scene, a taste of the outdoors or to bask in the sun at the number one beach in the country, Sarasota is a definite must-visit city in Florida. Take a day to relax on the cooling white sands and calm waters of Siesta Key Beach, followed by an evening at the opera house or a performance by the Sarasota Cuban Ballet School. Explore your artistic side at the Ringling Museum of Art and luxuriate at Ca’ d’Zan — 1920’s grandeur at its finest.

If you crave a bit of Florida’s wild side, take a trip to Myakka River State Park: one of Florida’s oldest and largest state parks. From scenic drives and trails to boardwalks made ideal for gator-watching, the 58 square miles of wetlands and prairies will leave you with a newfound soft spot for Florida. And if you’re hungry, you’re in luck: Sarasota’s rich cultural scene welcomes cuisine from around the world.

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Sarasota

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Tarpon Springs

Tarpon Springs, located north of Tampa, is one of my favorite cities in Florida. The city has an interesting history. Natural sponges were abundant in the waters surrounding Tarpon Springs and the sponge harvesting industry flourished in the city. Sponge divers from the Greek Dodecanese islands immigrated here in early 20th century. While the industry has shrunk since then, its heritage can be seen on the Historic Sponge Docks and in the Greek restaurants surrounding the Dodecanese Blvd.

The sponge docks are Tarpon Springs premier tourist attraction. Here you can still see sponge fishermen working on sponge boats. Visitors can take sponge boat trips and see fishermen dive for sponges. The nearby museum has interesting artifacts about the sponge industry. Visit any of the famous Greek restaurants to eat delicious gyros and try baklavas. With so many tourist attractions, Tarpon Springs is the perfect day trip or weekend destination on Florida’s Gulf Coast.

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Tarpon Springs

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Panama City Beach

Nestled along the Gulf of Mexico, northern Florida’s Panama City Beach is a classic spot for a coastal getaway. The sugary, white sands of this resort city are a big draw for families, spring breakers and nature lovers alike. Whether you want an indulgent afternoon under the sun or an action-packed day of water sports, you’ll find 27 miles of postcard-perfect coastline beaches to soothe your soul.

For a more remote getaway, hop on the ferry over to Shell Island, a quiet peninsula that showcases some of Florida’s most natural beauty. It’s also a popular location for boat tours. Nature lovers rejoice, the city’s also home to some of the best state parks including St. Andrew State Park, Camp Helen State Park, and Conservation Park. All with great nature trails for hiking.

For a little break from the sun, head over to Pier Park, an outdoor one-stop-shop for shopping, dining, and entertainment. Restaurants, lively beachside bars, live music venues, and dance clubs are all easily found under this sprawling outdoor center.

Traveling with kids in tow? You’ll find ample family activities, including the tropical-themed Coconut Creek Family Fun Park, Shipwreck Island Park and the Emerald Coast Mirror Maze. From escape rooms to mini golf, there’s something for everybody.

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Panama City Beach Fl

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Crystal River

Have you ever wanted to swim with manatees? Well, you can in Crystal River, Florida. Swimming with the wild manatees of Florida was such an incredible experience. Manatees are gentle and curious animals who would swim up to you to say “hi” and check you out.

Here in Crystal River, a small town 2-hour drive from Orlando, the months of November to May are considered manatee season. This is when manatees seek warmer water in the natural springs around Crystal River making the region the best place to see wild manatees in Florida. There are various tour operators that will take you on manatee tour with the possibility of jumping in the water with them. They’re protected species, so any interaction is strictly monitored. If you don’t feel like going into the water or joining a tour, you can also go to Three Sisters Spring, a nature reserve where you can view manatees from boardwalks.

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Crystal River

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St. Petersburg
The city of St. Petersburg has gone through a big transformation over the last 10-15 years.  Downtown St. Pete is the place to eat, shop, stay and explore. Filled with museums, great restaurants of all kinds, parks, music establishments, shopping, lovely bed and breakfast stays and hotels.   

The luxury historic hotel Vinoy sets the tone for downtown St. Pete, a perfect place to stay and enjoy everything offered in St. Petersburg.  The variety of eateries and bars is marvelous, authentic Indian, Chinese, Italian, Greek and more. Breakfast, brunch, lunch, and dinner are all served with many outdoor areas to enjoy your food.  If you love Jazz and spirits, then the place to go is Ruby’s Elixir, filled nightly with live entertainment from amazing musicians and singers. If you are craving a good cigar, go right next door to Central Cigars, pick one out and sit back with a drink.  Speaking of drinks, if you have champagne tastes and are craving a little bubbly and caviar… Flûte & Dram is for you! They have a wonderful selection along with a great tapas menu.

St. Petersburg is home to the Dali Museum, The James Museum, The St. Petersburg Museum of Fine Art, The Museum of History and more.  Shopping of all types is available from art to clothes.

A short drive from downtown and you will be at the famous beaches of St. Petersburg.  There are miles of white sand, water sports, shopping, eateries and beautiful accommodations including the famous Don Cesar. The City of St. Petersburg has something for everyone here in Florida!

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Clearwater

Clearwater Beach is a fabulous beach to visit with kids. With white sand beaches and the clear Gulf water lined with resorts, it’s no surprise that Clearwater is consistently named as one of the best beaches in the U.S.  We visited as part of a long weekend escape from the February snow. We enjoyed a delicious lunch at French’s Rockaway Grill, a Clearwater staple since 1981 with a breathtaking ocean view. After lunch, my husband and I sunk into the two beach chairs we rented and relaxed in the shade of the umbrella while our three kids built sand castles and played with the beach ball.

The Gulf waters were still a bit chilly, but we all dipped our toes in, and some of us braved the cold to explore a bit farther.  Ice & Cream provided the perfect afternoon treat – hand spun milkshakes. The Sunsets at Pier 60 Festival offers music, artisans and street performance every evening. Clearwater Beach is definitely a fun family destination, and we can’t wait to go back.

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Clearwater

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Tampa

With so many amazing cities in Florida, it makes it hard to choose which one to visit! If you are looking for kid-friendly activities, more than just relaxing on the beach, but you aren’t quite ready for Disney, then head to Tampa, Florida.

Tampa has so many wonderful attractions and with its international airport, it’s an easy destination to reach.

If you like theme parks, then head over to Busch Gardens for some thrills. Prefer a bit more of a laid back day with tons of animals? Then the Lowry Zoo or Florida Aquarium will be a delight. Love to spend time at the beach? There are a few beaches in Tampa or St. Pete is a short drive with some amazing resorts and white sandy beaches. There is even a pirate cruise where kids (and adults) can have a great time out on the sea.

You’ll never tire of the multitude of activities that Tampa has to offer! Want to read all about our favorite activities? Head over to our blog to see where we visited during our 10 day stay in Tampa

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Pirate Boat

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Florida Keys

Just about all of the cities along the drive down to the Florida Keys deserve a visit. The island chain just south of Miami is one of the most scenic drives you will likely ever do. There are many places to stop on the drive from Miami to Key West. Here are three places to stop for nature and history in the Florida Keys.

Starting with Key Largo, John Pennekamp State Park is the premier diving/snorkeling destination for all levels. If you enjoy fresh fish, there is no better place to get it than in the Florida Keys. Check out some of my favorite restaurants in the Upper Keys. Further down in Islamorada, Theatre of the Sea is a popular place to catch a marine show. Kids and adults alike will also enjoy feeding tarpon at Robbie’s.

Hawk’s Cay is a luxury resort located further down in Duck Key. It makes for a great place to stay if you want that resort type feel. Marathon is considered the heart of the Middle Keys, and a great halfway stop on this drive to the Florida Keys. Here you can rent a boat to a sandbar or go fishing near the Seven Mile Bridge. There are also fantastic local restaurants in Marathon.

Key West is the mecca of old-world Florida style and a great destination for a couples getaway. Quickly you will notice its’ charm, eclectic culture and find plenty of things to do. Scooter rentals are very popular in Key West as are sunset cruises. There are numerous tours that can be taken by catamaran, kayak, and yacht. A must do is a walk down the famous street lined with restaurants and bars, Duval Street, as well as a picture with the Southernmost sign.

Florida Keys

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Atlantic Coast

Miami

Miami is all about sun and fun.  Of course, you have to go to South Beach, where you can take a walking tour to admire the beautiful art deco buildings; while away the hours’ people watching over a leisurely lunch or dinner, with a cocktail in hand; and, of course, go to the beach for some sun and surf.

Want a break from the beach? Head to Little Havana for incredible Cuban food, vibrant art and, if you smoke, the best cigar makers in town.  You may want to take a speedboat sightseeing tour, zipping along past the beaches and beautiful homes of the rich and famous. You could also head to Lincoln Road for fantastic shopping and a coffee. Another option is to wander around the galleries and shops of Coconut Grove, with a stop at the nearby Vizcaya Museum and Gardens, a 1916 neo-Italian renaissance mansion. As the sun sets, Miami really comes to life and you can dance until dawn in one of the many clubs or bars.


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Miami

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Ft. Lauderdale

There are so many great things about living in Fort Lauderdale but truly the best part is being able to share what those things are with others!

Your first stop is a no brainer. Get to the beach! There are so many great beaches up and down both coasts but Fort Lauderdale is one that is meant for those who are ready to make friends and meet people from all over.

It’s well known for the local bars along the strip to ensure your day in the sun comes full circle with yummy island inspire drinks that are only a few feet away. Lulu’s Bait Shack is one of them with their famous fish bowls for sharing or for that person who’s really ready to get down and enjoy their vacation! They also have some great cajun eats on the menu!

Which brings me to the next must dos! Food! I can’t express enough how many great brunch spots there are across Fort Lauderdale. It is the thing to do! You can find so many locations that offer it on both Saturday and Sunday with so many different styles to choose from. Be sure to take some time to look up a brunch spot that fits your food style while you’re there!

One that is consistently popular since its’ opening is Tap 42. It has been a local stable for quite some time and has a great brunch menu. But really, you can head here any day of the week and you’ll find something delicious. (Especially on Mondays when their signature Prohibition Burger is only 5$!) They also recently opened a taco bar right next door that locals have been waiting for for a while so give Bar Rita a shot if you’re in the mood for Mexican instead!

Eats and beach, beach and eats! Come ready for both and you won’t be disappointed!

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Fort Lauderdale

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St. Augustine

One of our favorite cities in Florida, St. Augustine is rich in history, culture, and charm. Located an hour from the Florida/Georgia border, near the Atlantic coast, St. Augustine is the oldest city in the United States. Founded by the Spanish in 1565, St, Augustine boasts a historic city center filled with museums, forts, and things to do.

When visiting St. Augustine with kids, be sure to explore the Castillo San Marcos. It is the oldest masonry fort in the country. The Pirate & Treasure Museum, Fountain of Youth, and trolley tours are all great options on your trip to St. Augustine.

St. Augustine

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Cocoa Beach

Cocoa Beach is a chilled-out city with a fantastic beach which makes a great base for exploring the surrounding area. Plenty of people visit the Cocoa Beach area before departing on a cruise from nearby Port Canaveral, but the area definitely warrants a longer stay if you have the time.

Our kids loved the relaxed beach, which was the perfect temperature to enjoy in the evenings (it can get really hot in the daytime). The massive sand dunes are fun to explore when and the water is calm and warm, making it ultra-kid-friendly. This is a popular surfing beach also, with the Ron John Surf School offering beginner lessons all year round catering to kids as young as 5yo in a private lesson.

Close by, a visit to the Kennedy Space Centre (just a 30-minute drive away) is a fun and interactive way to learn about space. Cocoa Village is a quaint town worthy of a visit to experience the historic storefronts and arts and crafts markets.

For excellent food in Cocoa Beach, check out The Tiny Turtle for huge portions and a kid-friendly atmosphere. If you’ve still got an appetite, the Fat Donkey next door does amazing ice creams and desserts.

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Cocoa Beach

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Jacksonville

I flew into Jacksonville for a Northeast Florida road trip and fell in love with the city. We stayed right in the heart of Downtown Jacksonville with a view of the river. This was a great location for exploring the Riverside Arts Market an artisan and farmer’s market situated under the freeway every Saturday morning. Just down the street, we explored the Cummer Museum of Art & Gardens which features great art and the beautiful backyard garden along the riverfront.

Head across the river to the San Marco neighborhood filled with restaurants and shops. Be sure to grab a gourmet donut at The Good Dough which changes up their menu daily.

You can’t visit Florida and not hit the beach, so head out to Jacksonville Beach area which has miles of white sand beach surrounded by great shops and restaurants. If you like a more boutique beach vibe be sure to hit Atlantic Beach.

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Jacksonsville

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Stuart

Perched on Florida’s Treasure Coast, part way between Orlando and Miami, Stuart can go a little overlooked in favor of the state’s big-name players. But this colorful city has a lot to offer – including a lovely small-town feel in its historic downtown area. Busy weekend markets and regular events – including the free Sunday music concerts on the boardwalk – mean there’s always something going on. Throw in lots of cute independent shops and some amazing restaurants, and you have a nice, relaxing place to spend a weekend.

But Stuart’s biggest selling point is its prime location. From the town, you can easily reach some of the best attractions in Martin County. There’s Hobe Sound, a funky town with an amazing street art mural trail. Blowing Rocks preserve is just a short drive from Stuart, where you can watch the natural phenomenon of spray shooting through erosion holes in the limestone rocks as waves hit them – sometimes reaching heights of nearly 50 feet. And across the water from Stuart is Hutchinson Island, with a host of gorgeous – and notably quiet – beaches. There’s a lot to do in Stuart, Florida, so I highly recommend adding it to any road trip.

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Stuart

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Delray Beach

Last year I did a two-month road trip across the United States, starting my adventure in Florida. One of my favorite cities in Florida had to be Delray Beach. Just a short train ride North of Miami, this gorgeous beach-side destination is often, unfairly said to be a retirement city, but I found endless fun things to do, places to eat, and of course, fun people to hang with. I checked into the family-run Cranes Beach House where I was honestly made to feel part of the family straight away. Talking to guests around the poolside Tiki Hut bar, it seemed many returned here year to year.

A must stop while in town is Sloane’s Ice Cream, home to some of the most creative ice pops I had in the US. For lunch or dinner, I highly recommend Caffe Luna Rosa on South Ocean Boulevard where the Coconut Crusted French Toast covered in strawberries was the stuff dreams are made of!

If you’re in town with kids or love anything vintage, be sure to stop by the Pinball Museum – a quirky place to spend an hour or two.

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Delray Beach

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Inland Florida

Orlando

Orlando is the theme park capital of the United States. Having four Disney World parks, two Universal Studios parks, Legoland, plenty of water parks, and countless family-friendly attractions. This city is usually pretty high on the list of best cities in Florida to vacation.

Orlando can be an expensive city to visit, especially if you are traveling with kids. Before your visit, be sure to do research on how to get discount tickets to Orlando attractions. There are many websites that offer Orlando hotel discounts and check the Universal, Disney, and Legoland pages for special offers.

Disney World is usually the place people head to first, so be sure to read these tips on visiting Disney and Disney Fastpass secrets. If you have older kids or you are a huge fan of Harry Potter, then Universal Studios and Islands of Adventure are two fantastic theme parks to visit.

Disney Family

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Kissimmee

When you think of Kissimmee, it’s easy to think of amusement parks but there is more to this city in central Florida than Disney World and Legoland. Beyond the mouse, you’ll find plenty of activities that allow you to escape the crowds.

The Showcase of Citrus is a roadside stand that has been in operation since 1989. Family-owned and operated this is your go-to place to pick all things citrus. If you prefer not to pick your own, you can purchase fresh fruit in the country store along with jams, jellies, and unique souvenir items. You’ll find plenty of fun photo ops, a gem mine, wine tasting, and the world’s largest monster truck safari.

Two other quirky attractions include the Florida Orange World, probably the most photographed roadside attraction in Florida, and the Monument of the States. Orange World is an orange-shaped store that holds the title of the world’s largest and is packed with fun orange and Florida inspired souvenirs. Monument of the States is a totem pole-like structure that was erected in 1943 and includes one rock from each of the fifty states.

Explore Florida’s cowboy heritage when you are transported back in time to an 1876-era cowboy camp at Lake Kissimmee State Park in nearby Lake Wales. Interact with the Cowboys, watch living history demonstrations and explore the rest of the park via hiking, boating, and camping.

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Kissimmee

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Tallahassee

Tallahassee, best known as the state capital of Florida and home of Florida State University, is generally a drive through town for most visitors. What many don’t know is that this city is a food mecca just waiting to be explored. Chefs around town are elevating the humble oyster and fried chicken to new levels. A little-known dessert called Hummingbird Cake is making waves across the region. Midtown Caboose has a burger menu longer than your arm, but its’ creative offerings like the S’mores Burger and PB&J Burger have people breaking out of their normal cheeseburger routine. Breweries, like Proof Brewing Company, are popping up around town, making it easy for even families to sample a pint while their kids play outside on the lawn.

The Lodge at Wakulla Springs has some of the best fried chicken and fried green tomatoes in the state, and this isn’t your typical lodge fair. Nope, the chef has elevated these southern staples to fine dining levels. While you’re at Wakulla Springs State Park,  hop on a boat tour to see manatees as they make their yearly migration up the springs to stay warm each winter. These lovable sea cows share the waters with gators, a number of birds looking down from the trees, and swimmers hanging out on the beach in front of the lodge every summer.

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Wakulla Springs

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Everglades

In my opinion, an absolute must in southern Florida is a trip to the Everglades. The Everglades National Park is the largest subtropical wilderness in the United States. Entrance into the park is $25 per vehicle and worth every cent! If you’re anything like me the main goal of your visit is to spot a gator. While we

saw plenty, I have heard of others not spotting any. Thus, don’t hyper-focus on searching for alligators and miss all the other wonders in the park! The Everglades Park is absolutely massive and you will see tons of vegetation, animals, birds, and people from all over. However, for the best chance at spotting an alligator, I recommend walking the Anhinga Trail. This trail is the first stop after paying at the entrance. The Anhinga trail is a short and an easy boardwalk stroll, so suitable for most ages and fitness levels. We saw 20+ alligators on this trail! Thus, if you only have the time or the energy for one trail, I recommend this one.

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Everglades

Florida Road Trip itinerary

Florida is one of the longest states to drive through or to get out of. Depending on where you start and what destinations you have in mind, a Florida road trip can take quite some time. 

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Best Cities in Florida to Visit

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7 thoughts on “Best Cities to Visit While on a Road Trip in Florida”

  1. So many great options! It really does look like a beautiful place! Would love to swim with manatees!!

  2. Whoever knew there was so much more to FL than just Disney World. I am itching to visit Sanibel and Marco Island!! Great idea to road trip in this state!!

  3. Love this! I grew up in Georgia and loved vacationing in Florida. My family has since moved and I’m dying to take my kids to Florida, I will definitely be using this in the future!

  4. We absolutely love visiting Florida but haven’t been to so many of these places! Thanks so much for the inspiration for our next visit

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