8 Underappreciated Towns to Visit in Florida

Florida’s best towns remain overlooked precisely because they are not built around mass tourism. Set along quiet coastlines, river bends, and inland corridors, these communities offer access to nature, historic streets, and everyday Florida life. The following towns stand out for what they have preserved rather than what they have added.

Winter Park

Less than 20 minutes north of Orlando, Winter Park offers the perfect blend of big city attractions with a cozy small town feel. Downtown has a super welcoming atmosphere with unique local businesses like the Writer's Block Bookstore on Park Avenue, and over 140 additional locales line the cobblestone street. The main stretch is also home to Central Park, one of the town’s fabulous green spaces known for its rose gardens and annual Winter Park Sidewalk Art Festival.

For even more stunning natural scenes, the Winter Park Chain of Lakes are perfect for kayaking, paddleboarding, and waterfront strolls. But the best way to behold the 6 lakes and their connecting canals is on a 1-hour Scenic Boat Tour. Make sure to follow this with a trip to any of Winter Park’s dazzling museums, like the Albin Polasek Museum & Sculpture Gardens or the Charles Hosmer Morse Museum of American Art.

Winter Garden

Also a short drive from bustling Orlando, the picturesque town of Winter Garden borders beautiful Lake Apopka. Spanning 30,909 acres, the public lake is the 4th largest in Florida, best viewed from scenic Newton Park. Visitors can enjoy sunsets from the boardwalk, let kids loose at the playground, and enjoy a peaceful lakeside lunch at one of the many picnic tables.

Just a few blocks from Newton Park, Winter Garden's vibrant downtown features a handsome range of restaurants and dessert parlors for those looking to eat out, including The Hangry Bison and Kelly's Homemade Ice Cream. The area's other attractions, including the SOBO Art Gallery, the renowned Garden Theatre, and the Winter Garden Farmers Market, provide the perfect follow-up. The market, held every Saturday from 8am to 1pm, features over 100 vendors selling an array of goods, from artisan crafts to locally sourced produce, making it a lovely addition to any weekend plans.

Vero Beach

On Florida’s Treasure Coast, Vero Beach is an adorable coastal town often overshadowed by the state’s more mainstream shores. But for those craving a tropical setting, this gorgeous “Gateway to the Tropics” should not be overlooked. Situated on the Atlantic Ocean and the Indian River Lagoon, Vero Beach promises endless relaxation, sunshine, and adventure.

Whether booking a wilderness cruise with Airboat Wilderness Rides or taking an award-winning Eco Boat Tour, the waters and wildlife are breathtaking from every angle. Others may prefer viewing the lagoon from land, in which case, the Historic Jungle Trail offers the best path with lush tropical surroundings. As for beachgoers, the town by all means lives up to its name, with 26 miles of stunning shores. Highlights include Golden Sands Park, Round Island Park, and Treasure Shores Park to name a few.

Dunnellon

While Florida is often associated with its dazzling oceanfront, the state's charming river towns are equally deserving of attention. Dunnellon, for instance, sits at the meeting point of two magnificent rivers: the Withlacoochee River and the spring-fed Rainbow River. Visits to Dunnellon call for magnificent river scenes, and paddling is the best way to breathe in the views. There are several rental services in town for just that, including Rainbow River Kayak Adventures or Rainbow River Canoe & Kayak.

Dunnellon's riverside bars offer the perfect intermission from paddling but also provide a truly distinctive experience. Whether you choose to unwind at The Blue Gator Tiki Bar & Restaurant on the Withlacoochee or Swampy's Bar & Grille on the Rainbow, the delectable food, refreshing drinks, and warm hospitality are unmatched. If you find yourself recharged, Rainbow Springs State Park beckons as the ideal next stop for more paddling or a dip in the spring's vivid blue waters.

Steinhatchee

Steinhatchee is another stunning river town with tons to see and do. Its namesake waterway, the Steinhatchee River, is a beloved paddling spot thanks to its moderately mellow waters. And with less than 1,000 locals, outdoor enthusiasts can appreciate the river’s splendor without the hassle of shoulder-to-shoulder crowds. But with views this pretty and attractions this great, Steinhatchee may not remain a hidden gem for long.

The 6-mile Steinhatchee River Paddling Trail offers an exciting journey beginning at Steinhatchee Falls, which also functions as a peaceful picnic area on land. Additional land-based attractions in this historic fishing village include seafood restaurants like Kathi’s Krab Shack and hiking paths at the Big Bend Wildlife Management Area. Although the annual Fiddler Crab Festival in February has already taken place, be sure to watch for the upcoming Sips & Sunsets Festival.

Mount Dora

Returning to central Florida, Mount Dora’s vibrant arts scene pairs beautifully with its picturesque waterfront. Named after Lake Dora, the town honors its namesake with attractions such as Grantham Point Park, an outdoor sanctuary featuring one of Florida’s few freshwater lighthouses. This 35-foot lighthouse makes an ideal setting for photos to remember your visit. A short path from there leads to Palm Island Park, where shaded marshland boardwalks provide excellent spots for wildlife observation.

As for Mount Dora’s arts scene, the Modernism Museum is an inspiring and worthwhile visit. But what truly sets Mount Dora apart is its reputation as a “Festival City.” With over 30 festivals throughout the year, including the Mount Dora Arts Festival, Mount Dora Viva La Frida Festival, and many more, there is always something to keep visitors busy.

Sanibel

Hugging the Gulf of Mexico, the breathtaking island community of Sanibel was one of the countless towns impacted by Hurricane Ian in 2022. But despite its ongoing recovery, the island's sunsets and beaches remain a spectacle worth witnessing firsthand. Lighthouse Beach, situated on the southern tip of the island, is widely considered the town's premier shoreline. In addition to the thousands of colorful seashells scattered across the golden sand, its historic 1884 lighthouse stands as a proud symbol of the town's resilience. For a break from the sand and sun, Sanibel is also home to countless museums celebrating its splendor, including The Bailey-Matthews National Shell Museum and the Sanibel Historical Museum.

Fernandina Beach

For a barrier island getaway on Florida’s Atlantic coast, the underrated town of Fernandina Beach is the ideal place for a more secluded beach escape. Just 13 miles long, Amelia Island is a treasure trove of sandy shores and Fernandina Beach features one of the best for families. In addition to its pristine white sand, Main Beach Park features picnic areas, a skate park, and an oceanfront mini-golf course.

Fort Clinch State Park, located near the northern tip of Amelia Island, is a prominent attraction in Fernandina Beach. Spanning 1,400 acres and offering scenic views of the Amelia River, the park features a variety of landscapes, including tidal marshes and sand dunes. Visitors can spend a full day exploring its diverse environments through activities like hiking, swimming, or searching for fossilized shark teeth.

Final Thoughts

While Florida’s popular towns and cities are well-known for good reason, they were once overlooked too. In 2024, consider exploring less crowded routes. You might discover the next big destination—just enjoy the peace from fewer visitors while it lasts. Whether you're spending a day at Winter Garden by the lake and catching a show at the Garden Theatre, or relaxing for a week on Sanibel Island's beaches, adventure is around every corner.