Saint Augustine, Florida- Large groups of visitors and tourists explore the array of shops near the end of Saint George street in Saint Augustine, Florida on an early January afternoon.

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

Tourists and locals shopping at the historic beach downtown of Tarpon Springs
Tourists and locals shopping at the historic beach downtown of Tarpon Springs. Editorial credit: /

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

People shopping in St. George Street in Saint Augustine, Florida
People shopping in St. George Street in Saint Augustine, Florida, via Andriy Blokhin /

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

Downtown Mount Dora in Florida
Downtown Mount Dora in Florida, via Nigel Jarvis /

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.


Visitors feeding fishes and pelicans in Islamorada, Florida
Visitors feeding fishes and pelicans in Islamorada, Florida

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

Retail stores on South Park Avenue in downtown Winter Park, Florida.
Retail stores on South Park Avenue in downtown Winter Park, Florida.

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
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.


Old building in Monticello, Florida
Old building in Monticello, Florida, via Sabrina Janelle Gordon /

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, Florida United States
Havana, Florida United States

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 runs through Havana, which is known as the friendliest town in Havana. Wanderings is a Miami-esque design center with the difference of the sound of locomotives rumbling in the background. Havana reminds visitors of simpler times when everyone waved to one another and held the door open for you.


The waterfront at Gulfport, Florida.
The waterfront at Gulfport, Florida.

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 the center of what the locals playfully call their "weirdness." The Gulfport Casino is at the end of Beach Boulevard, but it may not be what you think it is. It is an event venue with swing and tango dance classes and a tomb of Morris the Cat. This is a quirky little beach town that openly welcomes visitors into its eclectic universe.

Fernandina Beach

Main street of Historic town center of Fernandina Beach on Amelia Island, via peeterv /
Main street of Historic town center of Fernandina Beach on Amelia Island, via peeterv /

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 been part of the Main Street Program since 2015 and is known for its shops, dining, and annual festivals like Dickenson on Centre at Christmas time. Hola Cuban Cafe is an authentic Cuban restaurant that serves some of the best breakfast and lunch downtown. Historic inns like the Florida House Inn, built in 1847, make for an authentic visit.

Florida is a unique state, full of history, culture, and beautiful nature. Smaller towns like these add to the charm by being friendly and inviting to guests. Florida has much to offer, from antiquing in the panhandle to tropical beaches in the Keys. These ten towns have the classic "old Florida" feel; most are easily walkable.

The architecture ranges from French to Spanish and reminds visitors of yesteryear. Towns like Winter Park are also cultural meccas, which flawlessly intermingles with the quaintness of a small town. Then there is Gulfport, which adds a touch of "weirdness" to the sparkling waters of the bay that make it inviting. All these towns should be visited at least once, for they embody the best of Florida.

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