9 Towns in Florida with Vibrant Downtown Areas
Florida has a long and unique history, and the small towns, both inland and coastal, reflect its rich history through historical sites and vibrant downtown areas. St. Augustine offers fantastic live events, including Colonial reenactments. Artsy towns like Fernandina Beach host live events throughout the year and have one of the best downtown experiences in the state. What is unique is that these towns all offer something different while maintaining an authentic Florida atmosphere.
Out-of-state visitors probably envision the Keys when they think about Florida, and for legitimate reasons. The party atmosphere of Key West, along with some of the world's best offshore fishing and scuba diving, is alluring to many. Here are nine towns in Florida with vibrant downtown areas.
St. Augustine
St. Augustine was established in 1565 and is the oldest town in the US. The landmark town's historic downtown is one of the most vibrant in Florida. St. George Street is the hub for entertainment and watching live reenactments. It is a pedestrian-only road filled with shops and restaurants like the iconic Columbia. The road is across from the fort, one of the main attractions of St. Augustine.
The Castillo de San Marco is a 17th-century Spanish military structure and one of only two made of coquina. The soft limestone helped the fort absorb military attacks instead of cracking. The list of other historic attractions is lively and includes the Oldest Wooden Schoolhouse, the Old Jail, and the Oldest Store Museum. The nightlife is excellent, and visitors frequently run into period actors dressed like pirates, Colonialists, or wenches.
Fernandina Beach
Fernandina Beach is a historic town on Amelia Island in Northeast Florida. Its moniker, the Isle of Eight Flags, pays homage to those who have possessed the town throughout history. Today, pieces of all eight cultures are seen in the architecture and historical sites, which are unique to the area. The Victorian-era and brick storefronts that line the 50-block district include over 400 historic structures.
The Amelia Island Lighthouse (1838) is the oldest in Florida, the Palace Saloon (ca. 1903) is the oldest in the state, and the Florida House is the oldest hotel. Modern restaurants and amenities are interspersed in this remarkable history, including the authentic Hola! Cuban Cafe. Loading up on one of the cafe's espressos before exploring downtown should be at the top of any traveler's list.
Key West
The southernmost point in the continental US, Key West showcases history, fun, and world-class fishing and scuba diving. Duval Street is the main strip, where visitors will find most of the island town's history and fun events at night, like the Duval Crawl. The vibrant area has numerous famous bars, including the Hog's Breath, Sloppy Joes, Green Parrot, and other lively activities.
Sloppy Joes, a renowned bar since 1933, is a landmark in Old Town. It was a favorite haunt of Ernest Hemingway, one of the most notable residents of the Conch Republic. The famed novelist's home is available to tour and is inhabited by a family line of six-toed cats. One must not leave town without viewing a legendary sunset at Mallory Square.
Mount Dora
Mount Dora is a historic town known for its rich history and downtown area. It is on the banks of Lake Dora, home to the 35-foot Mount Dora Lighthouse. The lively town hosts more than 30 festivals a year, including the notable Mount Dora Arts Festival. The festival highlights the area's arts scene, especially at the Modernism Museum. The downtown is also famous for its diverse shopping scene.
The tree-lined downtown oozes Southern charm and features several genteel boutiques, restaurants, and antique shops. Vintage Goods and Through the Years Vintage are hubs for antiques. The Mount Dora Olive Oil Company is known for its vinegar, cooking oils, and herb-infused olive oils. This is a great town to visit any time of year for fun festivals, history, and exciting retail therapy.
Naples
Naples is an iconic town on Florida's Gulf Coast. The azure-colored water and white sugary sand connect with the famous downtown area, a world-renowned shopping destination with sophisticated dining options. 5th Avenue South is where high-end boutiques like Caroline's and Ally Baker's meet Tin City, a collection of multi-colored historic buildings with stores and dining. Southwest Florida charm combined with the upscale boutiques is part of what makes Naples so unique.
Along with the waterfront bars and eateries, visitors can find chef-inspired dining options within a few blocks, like Ocean Prime. Naples is also home to an electrifying arts and culture setting. Galleries like Emily Jane and Gallery One are in the shopping district, while the Gulfshore Playhouse performance theatre is on 8th Avenue South.
Micanopy
Micanopy is a classic southern town in Central Florida. The rustic town covers just over one square mile but has a fantastic array of 19th-century buildings, antique shops, and ancient oak trees towering over the streets. Cholokka Boulevard is the de facto Main Street and home to businesses like Lost Ark Antiques and Shady Oak Gallery.
The history of "The Town That Time Forgot" is explored at the Micanopy Historical Society Museum. The museum traces the town's roots as a central trading hub to its Native American roots. Breakfast should start at Mosswood Farm Store and Bakery in a 1910 cottage selling locally made products. Micanopy may be small, but it is big on history and has a beautiful downtown with many things to do and see.
Winter Park
Winter Park, near Orlando, is a quaint town with a clean aesthetic and a thriving downtown area. The Park Avenue District has many outside dining, museums, and shopping opportunities. The tree-canopied brick lines street wind past shops like Sultre and John Craig Clothier. Dining includes Bulla Gastrobar, Hillstone, and many more.
Park Avenue museums include the elegant Morse Museum of Art. The museum displays the world's most extensive collection of Louis Comfort Tiffany with jewelry, pottery, and glass art. The collection's centerpiece has to be the chapel interior the famed designer created for the World's Columbian Exposition in 1893. People travel to Park Avenue worldwide for its diverse cultural and entertainment value.
Dunedin
The small town of Dunedin takes communal pride in its variety of shops and breweries, all of them locally owned. Dunedin Brewery is the oldest in Florida, opening its doors in 1996. The Dunedin House of Beer is one of America's Premier Tap Houses, and there are several more in the walkable downtown area.
Shopping is a big attraction here, including diverse options like a Celtic shop, winery, antiques, and art galleries. Stirling Art Studios and Gallery is within walking distance of the shopping district and showcases many artists using different platforms. Biking trails connect the downtown area to the rest of town, and it is a great way to spend a warm afternoon in such a lovely town.
Tarpon Springs
Rooted in Greek culture, Tarpon Springs is a friendly community with many unique places of interest. The town's history began in the early 20th century when Greek sponge divers settled here. The Historic Sponge Docks are still available to explore, and there are numerous Greek restaurants and shops on Dodecanese Boulevard, like the famed Hellas Restaurant and Bakery.
Mykonos is another authentic Greek eatery near Athens Street. The Greektown Historic District offers self-guided audio tours and is highly recommended. Threaded into the Greek shops are Cuban cigar shops, another Florida staple. Shops include Don Estaban and Serafin de Cuba. Tarpon Springs stands out because of its Greek heritage and bustling historic downtown scene.
Florida has vibrant downtown areas, from the elegant downtown of Fernandina Beach to the Greek-inspired Tarpon Springs. Classic Southern towns like Micanopy represent old Florida charm, while historic Key West throws outstanding parties throughout the year. These nine towns are some of the best in Florida, with historic attractions and exciting live events.
St. Augustine draws many visitors not only for its live reenactments but also for its entertainment districts. Museums and other cultural sites abound, and there is always somewhere to go for a fun night out. A weekend stay downtown in any of these towns puts visitors within walking distance of the vibrant activities that make these towns stand apart.
