8 Charming Road Trip-Worthy Small Towns in Florida

Wondering where to go on your next trip? Check out the enchanting road trip-worthy small towns in Florida!

Florida attracts millions of visitors each and every year. But the Sunshine State has much more to offer than you might think. There are plenty of charming road trip-worthy small towns, some off the beaten path, with fascinating attributes of their own.

The best part about them is an endless array of picturesque outdoor fun, quaint boutiques, fantastic restaurants, and roadside attractions that anyone with a couple of days off and a sense of adventure can enjoy.

Many of them are on the beach, and all of them will guarantee you have a few days filled with charm, sunshine, and LOTS of relaxation. Here are our 8 favorite road trip-worthy small towns in Florida.

Click “Next” to begin exploring!

Palm Beach

While Palm Beach County is one of this state’s largest, most popular, and largest regions, this road trip-worthy small town is a 10-square-mile barrier island with a population of just under 10,000.

And even though it’s one of the wealthiest areas in tour country, this road trip-worthy small town somehow remains approachable, with stunning beaches and many things to see and do within a couple of square miles.

While here, you can stay at The Breakers to get a glitzy, old-school feel. Take a bike ride along the Palm Beach Lake Trail and check out the island’s multimillion-dollar estates, or shop at the boutiques and art galleries lining Worth Avenue, a.k.a. the Rodeo Drive of the East Coast.

The Henry Morrison Flagler Museum, initially home to the railroad tycoon, is another “Must-See” in Palm Beach. This Gilded Age mansion was Flagler’s wedding present to his third wife!

St. Augustine

About an hour’s drive from Jacksonville, St. Augustine Beach is full of quaint, locally-owned restaurants and cafes, allowing for a perfect road trip-worthy small town atmosphere.

Take a leisurely stroll or relax along the sand, play some sand volleyball, cool off at Splash Park, or try your luck for the latest catch at the fishing pier. But this area offers much more than that.

You can try stand-up paddleboarding, boogie boarding, surfing, or kiteboarding because many beachside businesses are scattered around to rent gear.

With just under 7,000 residents, this road trip-worthy small town is a 15-minute drive from famous restaurants, museums, and many other attractions in St. Augustine’s historic district, dating back to 1565.

Micanopy

At just over one mile long, this road trip-worthy small town is Florida’s self-proclaimed antiques capital! It’s typically considered a rural, sleepy town, so it earned the nickname “the little town that time forgot.”

But with a small population of about 600, the most active road, Cholokka Boulevard, is lined with standard Florida architecture, antique storefronts, and old oak trees covered in Spanish moss. Have you ever dreamed of vacationing at a mansion? We’ve got you covered.

This is where Herlong Mansion comes in. This charming bed-and-breakfast greets every guest with a warm cookie and a glass of wine. The rooms are all about old Florida glamour, and we get it, considering the property dates back to the early 1840s.

Mount Dora

With a population of about 16,000, Mount Dora is a relatively small central Florida town with big-time charm, especially in its quaint downtown area, where you’ll find many charming restaurants, antique shops, and even a few annual festivals that line the streets.

For instance, The Mount Dora Arts Festival, which is held the first weekend of February, is a yearly favorite, attracting about 200,000 travelers annually.

While here, we recommend checking out the museums dedicated to various subjects, from modern furniture to local history. Peppered with lakes and live oaks, this road trip-worthy small town’s slow pace is a refreshing taste of old Florida.

Venice

Dubbed one of the “Happiest Seaside Towns in America,” this road trip-worthy small town is an oasis you likely won’t find anywhere else.

Located in the heart of Sarasota County, this charming town features a magnificent shoreline, recreational parks, and a vibrant beach area that’s home to sensational dining and boutiques. Fun Fact: Venice is also known as the “Shark Tooth Capital of the World.”

So be sure to go shark teeth-collecting on Venice’s picturesque shores while here. Looking for a place to stay the night?

Gulf Shore Beach Resort features the Venice Inlet on one side and the Gulf of Mexico on the other, putting you smack-dab in the middle of a Florida beach paradise.

Sanibel Island

It’s pretty impossible for us to say which small town in Florida is the most charming because there are too many to count. But Sanibel is at the top of our list.

Renowned for its world-class shelling, this road trip-worthy small town also offers spectacular sunsets and a charismatic community sans fast-food restaurants, street lights, and bustling city noise.

While here, you can enjoy the relaxed ambiance and natural beauty of one of the Sunshine State’s most treasured gems.

Just off this state’s peninsula on the Gulf of Mexico, this location is an ideal seaside vacation spot, with miles upon miles of crystal-clear waters for fishing, boating, and snorkeling. Plus, you’ll find thousands of patterned seashells waiting to be collected.

Islamorada

If you’ve been looking for a brief getaway that combines your love of the Florida Keys with cocktails on the beach, seaside excursions, and tropical foods, look no further!

A mere two hours away from Miami, the four islands of Islamorada are well-known for having an upscale, small-town vibe with plenty of seafood restaurants, museums, boating, and, of course, lots of sunshine.

But beaches aside, this road trip-worthy small town is home to not one but two funky breweries we think you should visit: Islamorada Beer Company and Florida Keys Brewing Co. both brew local beers with Keys-inspired ingredients, from starfruit to key limes and honey.

If you want to make the most of the beach and boating, reserve your stay at a villa at Hadley House.

It’s near some of the Key’s most popular attractions and restaurants, with water sports, cocktails, and other activities like breweries and museums less than a five-minute drive away.

You can also take advantage of complimentary on-site kayaking and paddle boarding. Or, for an added fee, a private jet-skiing tour of the surrounding keys.

Vero Beach

Found along the Sunshine State’s Treasure Coast, Vero Beach is a refined getaway offering charming museums, scenic beaches, nature attractions, and lavish accommodations.

This lovely road trip-worthy small town, often called the “Hamptons of Florida,” is the ideal place to go if you want to decompress. So don’t for get your swimsuit! While here, get the whole experience by renting a golf cart to explore this remarkable seaside community.

If you’re a Gloria and Emilio Estefan fan, you’ll want to book a room at Vero Beach’s Costa d’Este. This glamorous hotel brings all the Miami flair to the Treasure Coast, from a luxurious spa retreat to fine dining, boutique shopping, and craft breweries.

Which one of these road trip-worthy small towns was your favorite? Be sure to let us know in the comments. And if you love the Sunshine state as much as we do, we also recommend reading: 5 Reasons You Should Visit Florida This Cold Winter