10 Most Inviting Towns in Florida
Florida is a unique and highly sought-after vacation destination for good reason. The state is topographically diverse, with wetlands, pine forests, and tropical beaches. It is an outdoor lover's ideal spot, but Florida offers much more.
Florida has an eclectic historical background, including cultures and architecture depicting the various flags it has flown under. From British, French, and Spanish to the Greek founders of Tarpon Springs, modern-day Florida reflects all these cultures. Let's explore Florida's ten most inviting towns that embody the best the state offers.
Tarpon Springs
Tarpon Springs became a commercial epicenter at the beginning of the 20th century when Greek sponge fishermen immigrated to this coastal town. The town still has a strong Greek culture, including the Historic Sponge Docks. Greek shops and restaurants are on the main drag, Dodecanese Boulevard.
Another notable historic site is the Nicholas Greek Orthodox Church, built in the 1940s. It has beautiful stained-glass windows and a marble altar. This charming and inviting town has culture, history, and a seaside atmosphere.
St. Augustine
Founded in 1565, St. Augustine is the country's oldest town and is practically overflowing with history. It is a small town with a "fishing problem" in local parlance and is an ideal walking town. A walk down historic St. George Street will introduce visitors to classic Spanish Architecture and small-town charm.
As you stroll down St. George Street, you will see actors in period-appropriate clothing walking around on their way to live reenactments, including a lively changing of the guard ceremony. Across the street from the historic district is the Castillo de San Marcos National Monument, a Spanish fort that defended the Atlantic trade route. St. Augustine is still small today, but the historic sites and friendly townspeople make it one of the most inviting towns in Florida.
Mount Dora
Mount Dora is located on the 4,500-acre Lake Dora and is a charming, historic town with quaint southern charm. The town is named for an early settler, Dora Ann Drawdy. The name "Mount" was added because the town is on a plateau 184 feet above sea level, a rare feat in Florida.
It is a temperate town, and it is fun to walk around and explore. Must-see structures include the Grantham Pointe Lighthouse, the historic Donnelly House, and the Village Antique Mall. Mount Dora is a walking town, but a guided historic trolley tour is necessary, especially during your first visit. Lakeside Inn is highly recommended as it is Florida's most historic hotel and exemplifies the town's spirit.
Islamorada
Islamorada is the sport fishing capital of the world and a tropical destination in the Florida Keys. It is a welcoming town that is quite used to visitors year-round. The small village includes six Keys, and the Theater of the Sea is a great way to view the marine life and coral.
Several excellent attractions are on land, such as the History of Diving Museum and the Windley Key Fossil Reef Geological State Park. Of course, there are beachside eateries and bars like Marker 88 and Green Turtle Inn. The latter was featured on Diners, Drive-Ins, and Dives. Between the natural beauty of the island and the friendly atmosphere, Islamorada is one of the best Florida towns to visit.
Winter Park
Winter Park is a charming town in central Florida near Orlando. It is an affluent town with open-air spaces like Central Park. It is known as a town of culture and arts, like the Charles Hosmer Morse Museum of American Art, which features Tiffany's fine glass art.
The Albin Polasek Museum & Sculpture Gardens features celebrated Czechian art and overlooks Lake Osceola. This is a pedestrian-friendly town with several boutique shopping districts that are fun to explore on foot. Other memorable museums and cultural centers are nearby, and combined with the outdoor activities, Winter Park is a friendly and inviting place for visitors.
Fort Walton Beach
Fort Walton Beach is a small southern beach town in Florida's panhandle region. The town is known for its white sand beaches and Native American history. The Indian Temple Mound Museum displays Native American artifacts, some of which are prehistoric.
This is a family-friendly vacation spot, especially in the Spring. The Gulfarium Marine Adventure Park and the Emerald Coast Science Center are popular family destinations. A perfect blend of country life and tropical beaches makes this a premier town to visit in Florida.
Monticello
Monticello, less than an hour away from the state capital of Tallahassee, is a quaint and historic town. It was named for Thomas Jefferson's famed Virginia estate, which the courthouse was modeled after. Outstanding historical buildings include the Perkins Opera House and the Monticello Old Jail Museum, both town landmarks.
Hiking trails are plentiful in Monticello, a sought-after destination for nature lovers. Three rivers are nearby: the Pinhook, Wacissa, and Aucilla, all in the St. Marks National Wildlife Refuge. There are also Indian Mounds and plenty of open spaces ideal for relaxing walks.
Havana
Havana is a small, almost remote town in the panhandle region that is an antique hub. Named after the capital of Cuba, the town grew to prominence due to the abundant tobacco crops and cigar-rolling centers. Main Street is the primary road through the quaint downtown that hosts yearly festivals. Upcoming festivals are the Honky Tonk'n Havana and the Plein Air Painting In The Shade.
The North Florida Arts Trail passes through Havana, renowned as the friendliest town in the area. Wanderings is a Miami-inspired design center, distinguished by the sound of rumbling locomotives in the background. Havana evokes a sense of simpler times when people waved to each other and held doors open.
Gulfport
Gulfport is a coastal town near St. Petersburg on Florida's Gulf Coast. It is a hub for artists and musicians. A walk through the downtown district introduces visitors to buskers and local art pieces for sale. Several waterfront parks, like Wood Ibis and Clam Bayou National Park, make ideal afternoon getaways.
Beach and Shore Boulevards run through downtown along the bay and are known locally for their quirky vibe, affectionately called the "weirdness." The Gulfport Casino, located at the end of Beach Boulevard, might surprise you—it isn't just a casino. It serves as an event venue offering swing and tango dance classes—and hosts the tomb of Morris the Cat. This charming, unconventional beach town openly embraces visitors, inviting them into its vibrant and eclectic world.
Fernandina Beach
Fernandina Beach is a throwback Florida town with a laid-back atmosphere on Amelia Island on the northeast coast. This area is known as "the Florida Keys of North Florida." The friendly conditions make it easy to see why. Fernandina has flown under eight flags since its founding, and Spanish, English, and French architecture are prominent in Old Town, the original town.
The town has participated in the Main Street Program since 2015 and is renowned for its shops, dining options, and yearly festivals such as Dickenson on Centre during Christmas. Hola Cuban Cafe offers authentic Cuban cuisine and is known for serving some of the best breakfast and lunch options downtown. Historic inns like the Florida House Inn, constructed in 1847, provide a genuine visiting experience.
Florida is a distinctive state rich in history, culture, and stunning natural scenery. Smaller towns there enhance the charm with their friendly and welcoming atmosphere. The state offers diverse attractions, from antique shopping in the panhandle to tropical beaches in the Keys. These ten towns capture the classic "old Florida" vibe, with most being easily walkable. Their architecture varies from French to Spanish styles, evoking a nostalgic feel. Towns like Winter Park serve as cultural hubs, seamlessly blending cultural vibrancy with small-town charm. Gulfport, meanwhile, introduces a quirky edge against the beautiful waters of the bay, making it especially inviting. Visiting these towns is a must, as they represent the best of Florida.
