13 Most Charming Towns in Florida to Explore!

When someone mentions visiting Florida, we often think of large cities such as Orlando, Tampa and Miami. However, if you enjoy the small town vibe, the Sunshine State has several rural communities that offer way more than pass-through, sleepy little town stereotypes. These charming small towns in Florida play host to snowbirds and visitors who are looking for less populated and quieter fun things to do and see! These hidden gems are tucked in quietly along Florida’s coastline and inland as well.

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Why You Should Explore These Most Charming Towns in Florida!

Florida is home to a plethora of charming towns that offer a more relaxed and less populated atmosphere. These towns and small cities pride themselves by boasting their natural beauty, historical charm and fun things to do!

We’ve narrowed down our search for some super fun relaxed and enjoyable small town getaways in Florida.


Bridge to Island Apalachicola Florida - Always On Liberty
Photo source: CANVA

Apalachicola, known for its rich maritime history and its role as a historic port town, is located in the panhandle on Florida’s Forgotten Coast along the Gulf of Mexico.

This city with small town vibe is known for its’ abundant oyster industry. Some of the finest oysters in the country are harvested in Apalachicola. Hence, making it the prime real estate to host their annual Apalachicola Seafood Festival showcasing the town’s seafood heritage.

Apalachicola is recognized for its well-preserved Old Florida 19th-century architecture that completes is unique southern charm.

And if you’re looking for a little outdoor experience, its’ proximity to St. George Island and the Apalachicola National Forest invites nature enthusiasts and those seeking a tranquil coastal retreat.

Crystal River

Crystal River Florida Small Towns - Always On Liberty-2

Located on Florida’s Nature Coast on the Gulf side, this seaside town is renowned for its unique natural attractions. In fact, this charming town serves as a gateway to the natural wonders of Florida’s Nature Coast!

Having been to Crystal River more times than I can count, there’s no question why it ranks up to being one of the best small towns in Florida. Crystal River is the Manatee Capital of the World! Just like snowbirds flock to Florida for the winter, so do hundreds to thousands of Manatees!

Visitors can get an up close and personal view of the endangered West Indian manatees in their natural habitat.

Even better, Crystal River is the only place in the world where you and your family can actually swim and snorkel with the Manatees at the Crystal River National Wildlife Refuge.

Or, if you’re an outdoor enthusiast, there’s plenty of opportunities to paddle, boat, fish, and birdwatch along the incredibly beautiful scenic waterways.

Now, if you’re more into history, you won’t want to miss visiting the Crystal River Archaeological State Park. It showcases pre-Columbian Native American burial mounds and artifacts.

✰ RELATED ✰  Complete Visitors Guide to Crystal River,  Florida


Dunedin Florida Small Towns - Always On Liberty

Don’t confuse the spelling with its’ pronunciation. I still laugh when I heard my husband call the town “Dune-din”! When in fact, Dunedin is properly pronounced, “Dun-eedee-din”.

Located on Florida’s mid Gulf Coast, Dunedin’s Scottish heritage, charming downtown area, and proximity to Honeymoon Island State Park is what brings visitors from all over.

The town’s annual Highland Games with the presence of a Scottish pipe band highlights this Gulf Coast small town community.

Also, Dunedin’s Main Street is a hub for local events, including the popular Dunedin International Film Festival and Dunedin Art Harvest.

Celebrated for its’ charming and walkable downtown area, visitors can enjoy lots of foodie cafes and restaurants as well as a good selection of boutique shops and art galleries.

What makes Dunedin even more of a notable small town in Florida is its’ commitment to environmental conservation and outdoor recreation. The Pinellas Trail running through the town and Honeymoon Island State Park invites outdoorsy types to enjoy hiking, biking, and beach activities.

Cedar Key

Cedar Key Florida Small Towns - Always On Liberty
Photo by Always On Liberty©

Another favorite small town favorite in Florida is Cedar Key. However, don’t confuse Cedar Key with the Florida Keys that are in the southern part of the Sunshine State. But still, you’ll definitely get that island vibe when visiting.

Cedar Key is another laid back ‘Old Florida’ island town that begs art and nature lovers to visit. It’s the perfect escape if you’re looking for a place to escape the busy Route 19 light-to-light traffic headache.

Their picturesque sunsets are magnificent as is the serene coastal atmosphere vibe. Cedar Key is one of the best small towns in Florida where you can go outside and play!

Book a fishing charter, rent a kayak or boat and visit Cedar Keys National Wildlife Refuge, whose 13 islands were once home to fish camps used by First Peoples. 

Cedar Key is known for its’ thriving seafood and shellfish industry. Hence, why you’ll rarely wait but a few minutes at any one of their locally-sourced cuisine restaurants.

But, what I also love about Cedar Key is it’s collection of art galleries showcasing local talented artists’ works.

And, let’s not forget the comfortable walk around the block to enjoy the town’s scenic landscapes, historic architecture, and tranquil, off-the-beaten-path coastal setting. 

Cedar Key locals are super friendly and social which makes it why it’s one of my favorite small towns in Florida.

Fernandina Beach

Amelia Island Fernandina Beach Florida Small Towns - Always On Liberty
Photo source: Amelia Island Fernandina Beach Local Network Facebook

We have a friend-couple who used to live in our former neighborhood near Louisville, Kentucky. They now live on Florida’s Atlantic Coast.

Which leads me to listing Fernandina Beach on Amelia Island as one of the best towns in Florida to visit. “Amy” shares their weekend getaways on Amelia Island that leaves me thirsting for that little island town adventure. I was so intrigued by her photos, I had to check this dreamy island town out myself.

Situated in northeast Florida on Amelia Island, Fernandina Beach, is known for its highly acclaimed, historic Victorian architecture. It’s a popular destination for tourists and even locals because of its’ historic district, charming streets, boutique shops, and foodie favorites.

Fernandina Beach, including Main Beach Park, is also known for its’ pristine beaches that make it the most sought after relaxing coastal destination.

And if you love seafood, you’ll definitely want to attend their annual Isle of Eight Flags Shrimp Festival that celebrates its maritime heritage and local shrimp industry.


Matlacha Florida Small Towns - Always On Liberty
Photo source: CANVA

I actually learned about Matlacha through one of my favorite, color-loving artists, Leoma Lovegrove who used to reside and sell her vibrant works of there.

Pronounced “Matt-la-shay”, this cutesy small town is situated on Florida’s southwest Gulf Coast. The best I could describe this Florida island town is a colorful, artsy, fishing village on an island near Cape Coral. And it’s waiting for you to come visit!

Matlacha is locally known for its’ abundant seafood cafes and vibrant art galleries that line the village streets. And when I say ‘art’, I’m talking about distinctive and colorful funky art shops and cottages that create quite a unique and picturesque atmosphere.

So yes! You should absolutely bring your camera! 

This eclectic, bubbly Florida island town is celebrated for its’ super fun fishing adventures; attracting anglers seeking the diverse marine life in its surrounding waters.

Matlacha’s laid-back small town charm and artistic presence offers visitors of all ages a quiet, off the beaten path experience in the ultimate picturesque seacoast setting.

✰ RELATED   Best Day Cruise Experiences in the U.S. – Sun, Sea & Smiles!

Mount Dora

Mt Dora Florida Small Towns - Always On Liberty
Photo source: Mount Dora Word of Mouth Facebook

Located on the shores of Lake Dora, Mount Dora, Florida is known for its picturesque downtown district, annual festivals, scenic views and lakeside fun.

Most noted for being called the “Festival City”, you’ve got to make sure you’re in town for their many different festivals, shows, Pow Wows, Regattas, parades, etc. There’s always something cool going on in Mount Dora!

My two favorites are the Mount Dora Arts Festival and the Mount Dora Craft Fair.

Aside from Mount Dora’s charm and historic presence, the town’s brick lined streets, quaint boutiques, art galleries, antique stores and relaxing cafes make the perfect setting for any Hallmark movie. 

And if you’re up for a super fun adventure, relax and enjoy a one-hour narrated historic trolley tour by a knowledgeable guide. Learn about Mount Dora’s past, present, and future on board a custom-built, climate-controlled, vintage Trolley Bus.

✰ RELATED ✰ Top Sightseeing Trolley Tours in the US *Hop-On Hop-Off Tours*


Naples Florida - Best Small Towns in Florida - Always On Liberty
Photo source: CANVA

If you’re visiting Florida and are looking for more of a luxury destination, then you should definitely put Naples on your bucket list.

Naples is well known for its’ upscale amenities and luxurious, posh lifestyle. The southwestern Florida town will spoil you as will the pristine white sugary sand beaches and glorious sunsets along the Gulf of Mexico.

Naples is highly regarded for its’ high-end shopping and dining experiences. Its’ famous Fifth Avenue South serves as a vibrant hub for cultural events, entertainment, sophisticated shopping and dining experiences.

It also has exemplary theaters and art galleries that appeal to all ages.

And while Naples is a town with class of its’ own, the subtropical climate makes it an even more attractive destination for outdoor activities. It’s one of the prime destinations for golfers and outdoor enthusiasts who enjoy water sports.

And if that’s not enough to get you giddy about Naples, do know that their 16 miles of beaches rank as some of the best in the entire world!


Seaside Florida Small Towns

Seaside, Florida is a picturesque master-planned community known for its pastel-colored houses, white picket fences, and a charming town center. This Florida Gulf Coast town actually reminds me of Michigan’s Upper Peninsula.

But, what put it on the map of notoriety is it’s the filming location for the iconic movie, The Truman Show.

However, aside from it’s Hollywood claim to fame, Seaside features a pedestrian-friendly, charming town center with quaint restaurants, shops and art galleries.

As with all of the other best towns I’ve listed thus so far, Seaside celebrates its’ laid-back beach vibe and innovative town planning and architecture.

✰ RELATED ✰  30+ Things to Do on Mackinac Island – Michigan’s “Unsalted” Island Paradise

St. Augustine

St. Augustine Florida - Best Small Towns in Florida - Always On Liberty
Photo source: CANVA

Affectionately known as “The Ancient City”, St. Augustine boasts its’ status as being the oldest city in the U.S. This nickname reflects the city’s rich history and well-preserved architecture from its Spanish colonial past.

But, don’t let the word ‘city’ lead you to think it’s a bustling metropolis like Orlando, Miami or Tampa. St. Augustine prides itself with it’s small-town vibe with its cobblestone streets, historic architecture, and Spanish colonial influence, arts and cuisine.

You’re surely going to want to enjoy the well-preserved Spanish colonial architecture and centuries-old National Landmark, the historic Castillo de San Marcos fortress. Also, check out the oldest wooden schoolhouse.

For a bit of outdoor adventure, trek off to the Fountain of Youth Archaeological Park. St. Augustine is a great place to enjoy an early morning sunrise walk along the waterfront and the scenic Matanzas Bay.

Tarpon Springs

Tarpon Springs Florida Small Towns - Always On Liberty
Photo by Always On Liberty©

Known as the “Sponge Capital of the World”, the town of Tarpon Springs, is renowned for its’s rich Greek heritage and maritime history.

Take time to walk along the sponge docks, see the actual boats and learn about how sponges are harvested from the Gulf of Mexico. Tarpon Springs also offers picturesque waterfront views and boat tours.

But seriously, we go to Tarpon Springs for the food! This Florida small town is known for its’ vibrant Greek community. Hence, their authentic Greek cuisine, bakeries, and cultural events that keep us coming back for second and third helpings!

Now, a little tidbit worth sharing since I’ve been going to Tarpon since I was a little girl. I highly recommend dining at Costas on Athens Street (kind of back alley). I can personally vouch you can get the best Greek lunch or dinner that’s fit for the gods!

And for you lady shoppers, be sure to check out Antonia’s Boutique and Gifts at 501 Dodecanese Boulevard on the corner adjacent from the visitor center and across from the parking lot (pay to park). They have gorgeous, beach wear and classy clothing lines like Lulu B apparel!

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Venice Florida Small Town
Photo source: Gulf Coast Vacation Rentals

If you guessed that Venice, Florida replicates Italy, you’re kind of right. Venice is known for its’ Renaissance-style and Italian-inspired architecture in it’s beautifully designed historic downtown area.

There, visitors can stroll amongst the high-end boutiques, whimsical shops, java stops and eateries.

And let’s not forget the town’s gorgeous Caspesen beach where the kids can hunt for prehistoric sharks teeth!

There’s also plenty of recreation parks and stunning shoreline along the Gulf of Mexico making Venice the ideal place to catch a beautiful and romantic coastal sunset!

Another town-size city, its’ famously intricate canal system earns its’ nickname “Venice of America”. The Venice Fishing Pier is another notable attraction, offering scenic views of the Gulf and opportunities for fishing and daytime or evening stroll.

✰ RELATED ✰  Best Places to See Manatees in Florida

Winter Park

Downtown Historic District in Winter Park Florida - Always On Liberty
Photo source: Winter Park Downtown Historic District (José Antonio Rendón)

My first impression of Winter Park, Florida wasn’t what I see today. I only remember the young adult scene (bars in 1981) which is a far cry from what it is today.

Now that I’m much older, mature and enjoy the finer side of life, this Florida small town favorite paints an entirely different picture.

Just a bit north of Orlando, Winter Park is known for its’ charming small town feel with meticulous tree-lined streets, upscale boutiques and fine dining establishments. It’s kind of like a whittled down version of Charleston or Savannah.

The town of Winter Park (okay, it’s really a pint-size city but who cares) is appreciated for its cultural attractions. Art lovers can enjoy a quiet afternoon in the Charles Hosmer Morse Museum of American Art with its’ renowned collection of Tiffany glass.

Winter Park is also home to Rollins College, adding an academic and artistic dimension to its cultural scene.

For you outdoorsy types, you have to check out their beautifully scenic lakes, particularly the Chain of Lakes, offering opportunities for fishing, paddling, and boating.

Winter Park also has a beautiful, shady park that covers 23.16 acres on Lake Baldwin. The park is one of two city parks which boasts a sandy beach.

RVing to Florida? 

If you’re planning on taking your RV to these charming Florida small towns, it’s important to plan ahead so you can experience more with less stress!

This is why we use RV LIFE Trip Wizard. It helps us get to our destinations utilizing RV-friendly routes specific to our RV and travel preferences. You can try before you buy FREE for 7-Days!

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Final thoughts

Best Small Towns in Florida - Always On Liberty
Photo source: CANVA

Florida is way more than high-energy, cities, head-spinning theme parks and big ticket attractions. As you see, there’s a plethora of small towns in Florida that gets you away from the bustling metropolis.

So, let’s get busy mapping out these fun and friendly destinations that provide a modern glimpse of Old Florida charm, diverse landscapes, and outdoor adventure!

Best Small Towns in Florida - Always On Liberty

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