10 Darling Small Towns In Florida

Winter Park

While far from being a huge metropolitan, Winter Park’s amazing attractions, amenities, and shopping district can rival Florida’s big cities. The city was founded as a resort in the late 19th century and continues to draw tourists looking for some retail therapy in a charming locale. You can get a scenic boat tour at Lake Osceola, stroll through the beautiful Mead Botanical Garden, and tour the Charles Hosmer Morse Museum of American Art before hitting Park Avenue’s upscale boutiques and world-class restaurants.

The AVA MediterrAegean’s modern Greek dining, the South Asian-bohemian boutique of Kathmandu Tribalasia, and Peterbrooke Chocolatier are just some of the can’t-miss stores in this shopaholic and gourmet paradise. The best part? Winter Park is only a 20-minute north of Orlando, so you don’t have to travel far to reach this cute shopping haven.

Apalachicola

The beautiful coastal town of Apalachicola, Florida

For a Florida vacation full of seafood, maritime history, and fishing, a visit to Apalachicola might be what you need. A welcoming port town on the Emerald Coast, it earned its “Oyster Town” nickname for producing 90% of oysters in Florida. Head over there on the first weekend of November to join the Florida Seafood Festival, the state’s oldest seafood jamboree, to taste the freshest bounties from the gulf.

Fishing friends can try to reel in some good catch with Apalachicola Bay Fishing and Cruises. However, if you want to bait and catch the spectral kind, the Apalach Ghost Tour can aid you in ghost hunting. Don’t clam up when these ghosts say shell-o from the oyster side!

Anna Maria

Situated on an island of the same name, you will fall in love with Anna Maria for its vast white-sand shores and close-knit community. Bean Point Beach alone stretches far into the waters, which gives ample space and views for beach loungers and sunbathers. Want a park that faces Tampa Bay? Bayfront Park, on the other side of the island, is a cozy seaside nook for picnickers and park-goers.

But it is not just its breathtaking beaches that have charmed tourists and locals alike to Anna Maria. As seen in its mini museum, the Anna Maria Island Historical Society, proof of its chummy neighborhood includes a preserved cottage saved by locals when it was once swept to sea! Once part of the Anna Maria City Pier before its renovation, you will also find some engraved planks with resident names on display.

Crystal River

Crystal River is one of Florida’s most beloved small towns for its sparkling blue waters and adorable manatees! It hosts the only National Wildlife Refuge in the country that was purposely made to protect the habitat of Florida’s official marine animal. These majestic creatures visit Crystal River to stay warm, and you can meet and swim with them through services like Fun 2 Dive Charters and Explorida. Get an eco-tour at Crystal River Preserve State Park to learn more about the local government’s preservation efforts for these animals.

Other than swimming with manatees, Crystal River is also renowned for the freshwater springs of Three Sisters Springs and the burial mounds at its Archeological State Park. After your outdoor adventures, treat yourself to the freshest seafood at Dan’s Clam Stand and Cajun Jimmy’s. Great food, sublime waterscapes, and a great neighborhood—there’s a reason the manatees keep coming back!

Islamorada

If you can’t get enough of Florida’s wildlife, visit Islamorada, a tiny coastal village between Miami and Key West. Many visitors adore it for its attractions that bridge marine animals to curious kids and adults looking to educate themselves (and see cute animals, of course). Theater of the Sea hosts the only dolphin show in the Florida Keys, including interactions with marine animals and other wildlife. Want to get up close with Islamorada’s underwater spectacles outside the marine park? The Florida Keys Dive Center right across can take you on a SCUBA tour!

Diving isn’t for everyone, but the History of Diving Museum can satiate your diving curiosity on land. Islamorada is also known as the “Sport-Fishing Capital of the World,” which you can test through Fishinpole Sportfishing and LegaSea Charters. Don’t leave Islamorada without a picture of the humongous lobster statue at Rain Barrel Village!

Venice

Thanks to its Italian Renaissance-style architecture and “Shark Tooth Capital of the World” title, Venice is brimming with character that has charmed many visitors over the years. Due to being underwater and home to sharks during prehistoric times, modern Venice is now a treasure trove of fossilized shark teeth! Find out more at the annual Venice Sharks Tooth Festival in April. While here, try to spot tiny shark statues peppered around the city!

Aside from its shark-tastic attractions, downtown Venice is filled with historic structures evocative of its namesake Italian burg. Venice Museum, the Triangle Inn, and Hotel Venice are just some of its must-see historical spots. With stellar views and unique attractions, it’s no surprise it was included in StorageCafe’s Top 10 U.S. Suburbs for City-Like Living.

Tarpon Springs

Sea sponges and strong Greek roots are the stars in Tarpon Springs! Because of its successful sponge business and hard-working Greek immigrants in the 1800s, Tarpon Springs became known as the “Sponge Capital of the World”. They started many restaurants and festivals reflecting their Greek heritage. Meander along Dodecanese Boulevard, the town’s Greek epicenter, to see sea sponge shops, docked sponge boats, and authentic Greek cuisine. Do some shopping at The Sponge Exchange and enjoy chicken souvlaki at the iconic Tarpon Springs eatery of Hellas.

Every November, the town honors its heritage through the Tarpon Springs Seafood Festival set along the historic Sponge Docks down the boulevard. Expect lots of fresh seafood, sponge-themed souvenirs, and boatloads of nautical fun in this beautiful Greece-like haven in West Florida.

St. Augustine

Step into the past with St. Augustine’s museums and historical sites! As the “Nation’s Oldest City” due to being the longest still-inhabited settlement, St. Augustine is the perfect place in Florida to learn about the country’s historical events. The Castillo de San Marcos fort, built to protect the city from pirates and British forces, is the most-visited spot in town. There is also the Colonial Quarter, which takes you on an immersive journey full of exhibits, demonstrations, and interactive activities that showcase the four different eras of the city’s history.

After your trip down America’s memory lane, stroll through St. Augustine’s adorable narrow streets downtown for yummy eats and amusing souvenir shopping. Some of the highlights include Prohibition Kitchen’s 1920s retro-chic watering hole, Prehistoric Florida’s collector items, and Columbia Restaurant’s traditional Spanish dishes. Learning about the past is exciting when you do it in St. Augustine!

Rosemary Beach

Although not as historically rich and old as other towns on this list, Rosemary Beach wows visitors with its French Quarter-inspired architecture, modern community, and pools and beach that scream “ultimate summer getaway!” Prepare for a beautiful stay at the European-style boutique hotel of Rosemary Beach Inn. Then, cool down in any of its four stunning pools with French West Indies, Cabana, and Mediterranean design styles. Its picturesque namesake beach is a surprise, too!

Enrichment for the mind, body, and soul is also available via the charming nook of The Hidden Lantern Bookstore and bike rentals from Bamboo Bicycle Co. However, what is inspiring about Rosemary Beach is its neo-traditional beach community mixed with New Urbanism. This kind of urban planning promotes eco-friendly and walkable habitats—at the heart of Rosemary Beach.

Mount Dora

If you like festivals, you’d love Mount Dora—a town near Orlando nicknamed “Festival City” for having over 30 festivals yearly! There is something for everyone here, whether you like the arts (Mount Dora Arts Festival and Mount Dora Craft Fair), sailing (Sailboat Regatta), poetry (Jane Austen Fest), Scottish culture (Scottish Highland Festival), and even blueberries (Mount Dora Blueberry Festival).

But Mount Dora’s charms don’t stop at its events. Its waterfront views of Lake Dora, the iconic Mount Dora Lighthouse at Grantham Park, and the gallery-restaurant hybrid of the Modernism Museum have won the hearts of many visitors.

Final Thoughts

If you ask many Americans and international tourists, Florida is hard not to love for its beaches and sunny location. However, this sentiment excludes its megalopolises like Orlando, Miami, Jacksonville, and Tampa. As pointed out on this list, the small towns in Florida are every bit as lovable and a total darling in many people’s eyes!

Apalachicola’s love for oysters, Crystal River’s manatees, Tarpon Spring’s sponges and Greek heritage, and Mount Dora’s festive penchant are just a tiny taste of Florida’s endearing communities and culture.