8 Most Charming Town Squares In Florida

Florida is one of the most visited states in the nation, and for good reason. The Sunshine State has flown under several flags, including Spanish, and has a diverse tapestry of history that is still evident today. Towns like Fernandina and St. Augustine are filled with historic structures, many of which are Spanish-style and give the cities a unique atmosphere. Florida also features small towns that reflect the best of the state with distinctive sights, food, and culture.

This old Florida vibe may not be as apparent as the historic fishing village of Apalachicola. The area revolves around remarkable town squares in place when the town was built, and each one has a unique story to tell. Whether seeking history or a tranquil retreat, these are Florida's most charming town squares.

Mount Dora

Historic Mount Dora, in central Florida, is an ideal destination for romance and relaxation. Centered around Lake Dora, the town is known for bed and breakfast inns like the landmark Lakeside Inn and historic sites like the Mount Dora Lighthouse at Grantham Park. The lighthouse is significant as one of the few inland lighthouses in the state.

The lakeside town is also known for hosting over 30 festivals a year, including the Mount Dora Arts Festival. The 51st rendition will be held in January 2026 and will include more than 300 artists on historic Main Street. Art lovers should not miss the Modernism Museum's incredible sculptures and exhibits.

Fernandina Beach

Historic Fernandian Beach on Amelia Island is a fantastic array of architecture, charming inns, and unique finds, including the oldest bar in Florida. The Palace Saloon has operated since 1903 on Centre Street, the main drag through the historic district. Exploring the roads on foot is the best way to get around among the historic brick buildings.

Hola Cuban Cafe and 1928 Cuban Bistro nod to Fernandina's Spanish roots and are popular among locals and visitors. Winter is a fantastic time to visit when downtown becomes a wonderland. Dickens on Centre takes place every November through December with parades, events, and street shopping, adding to the beach town's charm.

St. Augustine

Historic St. Augustine is the oldest settled community in the U.S. and one of the most captivating towns in Florida. The historic district around Cuna Street, one of the oldest in the nation, is filled with landmark sites, restaurants, and a vibrant nightlife. Across from the area is the Castillo de San Marcos, a Spanish fortification, and one of the primary reasons families visit the city.

Other cultural attractions include the Lightner Museum, an immersive experience uniquely combining art and history. Bed and breakfast inns are the best way to spend time in St. Augustine. The Augustin Inn is in the heart of historic downtown, near the main attractions, and provides a quaint setting, a short walking distance from the sites that make this city so captivating.

Seaside

Seaside is a planned community in the New Urbanist style on Florida's Emerald Coast. The pedestrian-friendly streets extend from the town square, a renowned shopping and dining district. After a morning of shopping, dine at the Daytrader Tiki Bar and Restaurant at the iconic Coleman Beach Pavilion entrance for Polynesian food and sea breezes.

Make sure to visit Sundog Books before heading to the beach. The family-owned bookstore has been a landmark for over 30 years, a favorite of locals and visitors in the heart of downtown. There are many other unique finds in the town square area, each adding charm to this planned community on the Emerald Coast. Seaside is the ideal destination for lazy days strolling the town square, with stunning Gulf views and a vibrant downtown area.

Rosemary Beach

Rosemary Beach is an elegant, European-designed town on the Emerald Coast that revolves around its Town Center. The European-colonial architecture wraps around the shopping center, which includes apartments and rooftop bars like Pescado Seafood and Rooftop Bar. You can also lodge at the Pearl Hotel, which features the Havana Beach Bar and Grill.

The beachfront hotel features luxurious rooms, beachfront views, and terraces, perfect for soaking up the rays. Downtown is pure Florida charm with outside dining and shoppers milling about. The brick sidewalks wind through many shops, like the Cork and Barrel, and many others. This is the ideal destination for walking around in the sunshine, shopping, and spending a relaxing day gazing at the unique structures.

Micanopy

Downtown Micanopy centers around Cholokka Boulevard, the small town's main drag. The rustic brick buildings are a nod to the past and are known for their numerous antique stores. Shops include the Antique City Mall and Wren Wood Antiques. The slower pace of life is one of the most attractive qualities of this town, and spending a day walking under the majestic oaks is remarkable. The shady limbs framing the historic storefronts add a peaceful ambience to the downtown area, another distinctive element.

Mosswood Farm Store and Bakehouse are must-stops for any visit. Housed in a 1910 residence, the family-owned general store offers homemade jellies, pickles, and other local flavors. For such a small town, Micanopy has much to offer its visitors, and the friendly community makes it even more charming. The atmosphere and unique finds reflect the best aspects of the state, making it one of the best towns to visit in Florida.

Dunedin

Dunedin is famous for many things, and its pedestrian-friendly downtown area is among the top reasons to visit. The district centers around Main Street, featuring multi-colored storefronts and eateries, such as Skip's Bar and Grill, which is pet-friendly. Located on the Intracoastal Waterway, downtown is a premier location for watching the sunset, especially on Caledesi Island, which is accessible by ferry that docks at the Dunedin Marina.

There is much to see and do on Main Street, and many of the restaurants and boutiques offer Florida decor to set the tone for this Florida town. Ending the day with a brew at Caledonia Brewing is a must. Although there are several other breweries offering artisanal beers downtown, Caledonia is housed in the 1924 Dunedin Times Building, adding to the charming aesthetic of the area.

Apalachicola

The historic fishing village of Apalachicola centers around six distinctive squares. Gorrie Square's name honors a 20th-century town physician. It is home to landmarks such as Trinity Episcopal Church. Strolling around the squares and taking in the historical sites are two primary reasons that Appalachicola is popular among travelers.

City Square is another original town square. Today, the square is known for its historic Chestnut Street Cemetery, which contains the graves of many soldiers from both sides of the Civil War. Visiting the fishing docks is a must, and if you arrive early enough, you can see the fishing boats coming and going through the harbor. The architectural history, elegant seafood restaurants, and commercial fishing boats contribute to a pleasant aesthetic in this charming fishing village, making it an unbeatable weekend destination.

These eight town square areas are the most charming in Florida for various reasons. Each district has a unique story to tell, and each embraces the true spirit of Florida. Residents know this atmosphere as "old Florida," and these areas are the best at honoring this cultural heritage. Many are older than the state itself, and each one is worth visiting for at least one day.

The diversity of the regions is also a distinguishing characteristic of the small towns. Seaside is a planned community designed as a shopper's haven with a European aesthetic. Micanopy is an entirely different historic town, yet each one is an ideal destination for those seeking to soak in an authentic Florida atmosphere. Town squares reflect the communal bond of the residents, and these eight fit the bill uniquely and charmingly.