These 11 Towns In Florida Have The Best Main Streets
Main Street USA has almost become a lost art form, giving way to box stores and concrete jungles. Thankfully, there are towns still around that embrace the communal spirit these areas offer while adding subtle, modern touches to keep the city moving forward. Florida is a distinctive example of this phenomenon, blending "old Florida" with contemporary settings to fuel its thriving tourism industry.
These 11 towns have the best Main Streets in Florida, with an eclectic blend of vintage architecture, compact streetscapes, and a dose of small-town life, especially in Fernandina Beach and Mount Dora. Florida has been ruled by various governments, including British and Spanish rule, and its scenery reflects the characteristics of each, offering an assortment of architectural styles, culinary traditions, and heritage sites.
St. Augustine
St. George Street is the main artery of historic St. Augustine and sums up the city's centuries-old history like a succinct ending to a play. The pedestrian-only artery is wall-to-wall with historic landmarks, including the Oldest Wooden Schoolhouse, colonial-era buildings, and Florida-centric restaurants like The Columbia. They bookend St. George Street, holding together the vendors, cobblestone pathways, and hidden wonders like Spanish Centinelas in the 17th century.
The City Gates are also on this road, giving visitors a glimpse into centuries of St. Augustine's Spanish, British, and American history. Visitors should consider booking a room at the St. George Inn on the north end of the road. It is in the heart of the historic district across from the famed Castillo de San Marcos and within walking distance of the main attractions.
Mount Dora
Historic Mount Dora, home to the only inland lighthouse in Florida, features an incredible historic district that serves as the town's main strip. The lakeside village revolves around Lake Dora, and a stay at the historic Lakeside Inn lets the aesthetic really sink in. Walking through the stone gateposts of the oldest continuously operating hotel in Florida is an invitation to the past, endowing every visit with charm and tranquility.
Several downtown restaurants align with this tranquil view of Mount Dora, including 1921 Mount Dora and Pisces Rising. 1921 has a forward-thinking approach to fresh and local ingredients in a converted 1921 home. Pisces Rising is in a restored 1919 home and specializes in a traditional Florida menu and outdoor spaces, providing authentic lakeside vibes that complement any visit to the town.
Key West
Key West's Duval Street could be considered the "Party Capital" of Florida because of its raucous bars and epic events. It is also a place of history, and it is this history that has made it the fun resort town it is today. Famed author Ernest Hemingway said about his beloved island hideaway, “It’s the best place I’ve ever been, anytime, anywhere. Flowers, tamarind trees, guava trees, coconut palms... [I] got tight last night on absinthe and did knife tricks," which sums up the aura of the entertainment district even today.
Hemingway's favorite haunt was Sloppy Joe's, and today it remains an essential stop on Duval Street, with the author's face on its sign. There are other ways to experience the district without waking up with a hangover at the Key West Aquarium and the Audubon House and Tropical Gardens. Each provides an insider's look at the ecosystem and tropical climate that support Key West's thriving environment.
Micanopy
Micanopy is a tiny Central Florida town but big on history and antiques, a significant draw for many visitors. This "old Florida" paragon is less than 1,000 people, but the tree-lined streets and slower pace of life call to those looking for a quiet and scenic getaway. The compact area makes it easy to shop at various antique dealers, such as Antique City Mall and Wren Wood Antiques, each attracting visitors from all over.
Visitors are invited to study the area through painting at Micanopy Outpost, which specializes in local work showcasing the small village over the years. Downtown offers several places to take a break from shopping, including the local favorite Old Florida Cafe for a traditional lunch. Just down the road from the community hub are heritage sites, including Micanopy Historic Cemetery, which rounds out a day in this authentic Florida town.
Tarpon Springs
The Greek fishing village of Tarpon Springs on Florida's Gulf Coast is one of the state's most distinctive towns. Dodecanese Boulevard is the main artery, and it is here that the historic sponge docks can be found, along with a variety of Greek restaurants and goods, at places like iconic Mykonos. Visitors can also sample cigars hand-rolled the Cuban way, a rich Florida tradition, at Don Estaban and Serafin de Cuba.
The Greek heritage epicenter has plenty to offer for extended stays, including cultural institutions such as the historic Sponge Exchange, where the city's founding fishermen offloaded sponges. Now, it is a shopping hub with over 30 local boutiques, like My Little Black Dress. Tarpon Springs is a fascinating town to discover, and one trip is never enough.
Venice
Although Venice is famous as the "Shark Tooth Capital of the World," it also has a fantastic historic district centered on Venice Avenue, with Tampa Avenue just as prominent. The heart of the district is Centennial Park, an open-air space that often hosts live music. Park goers will also find the Venice MainStreet kiosk, filled with information about the historic district for a self-guided tour.
Downtown was built in the 1920s, and the Roaring 20s motif is still going strong. This is evident at the landmark San Marco Hotel on Tampa Avenue, completed in 1926. Walking around in the salty breezes feels like a simpler time in downtown Venice, with stunning buildings and a lively community that make it worth at least one visit.
Fernandina Beach
With its shrimp boats bobbing in the harbor next to oak-shaded streets, both visitors and locals enjoy the island life in this North Florida town. Known as the "Isle of Eight Flags" due to shifting sovereignties over the centuries, Centre Street downtown features elements of each, resulting in a scenic, eclectic downtown section.
Downtown has an abundance of fascinating histories and venues, like the Palace Saloon, the oldest bar in Florida. There is also an abundance of bed and breakfast inns in the area to consider, like the iconic Florida House Inn, circa 1852, one of he oldest continuously operating hotels in the state.
Siesta Key
For those seeking a tropical getaway without needing a passport, Siesta Key should be on your radar. Siesta Key Village, the island's downtown, is surrounded by clear blue water and palm-tree-lined streets, offering an unbeatable coastal aesthetic. Folks can get around Ocean Boulevard, the main road, and the island on the free open-air trolley while looking for high-end boutiques like Rochelle's on Siesta or the Foxy Lady.
Of course, being outside and watching the signature sunsets Southwest Florida is known for is paramount, and several restaurants offer outdoor seating for this purpose. Options range from casual at Siesta Key Oyster Bar to refined at Mattison's Forty-One in nearby Sarasota. Each features the coastal atmosphere that has made Siesta Key one of the world's premier beach destinations.
DeLand
Downtown DeLand's Historic Garden District features cobblestone walks and Mediterranean Revival architecture, giving it an old-world feel. It is an artsy place, underscored by the annual DeLand Fall Festival of the Arts, which draws thousands of people every year to enjoy its more than 150 Juried artists, pottery, and other media. Landmarks include the 1884 DeLand Hall, part of Stetson University, and the oldest building in continuous educational use.
Across the way is the elegant Elizabeth Hall, built in 1892 and modeled after Independence Hall in Philadelphia. However, DeLand is more than just old buildings; it also features a vibrant food scene, including The Parched Oak and several other casual and refined dining options.
Naples
Downtown Naples is a high-end shopper's paradise, with beach views and establishments that attract visitors from all over the world. The shopping district centers around Fifth Avenue South and Third Street South, known for upscale shops and the landmark Naples Pier. The renowned district stretches from Tamiami Trail to the Gulf of America in Old Naples and includes shops from Anne Fontaine and many other notable fashion brands.
Fine art is easy to find in the shopping district at notable galleries such as Aldo Castillo Gallery, David Beavis Fine Art, and many others. This premier destination shows a different side of Florida life without losing its charm. Lunch at Caffe Milano is a prime example of this appeal, mixing an elevated menu with a relaxed atmosphere.
Dunedin
Main Street Dunedin is on the Intracoastal Waterway and lined with artisan breweries that have made a splash in Florida and galleries. Stroll the area and stop at Caledonia's for a brew in a building erected in 1925 as the home of the Dunedin Times newspaper. Afterward, take a stroll in Pioneer Park, maybe catching an outdoor concert or farmer's market.
Dunedin Downtown Market is an essential stop for many tourists and locals, open on Saturdays year-round and on Fridays during the first half of the year. The open-air market is a great way to meet the locals and absorb the atmosphere while browsing for unique finds. It provides a prototypical way to spend a Florida afternoon and a way to explore the neighborhood.
These 11 Florida Main Streets represent the best of the state's eclectic history, offering visitors a glimpse of the past while enjoying luxurious lodging and sophisticated dining. The variety is the best aspect of the regions, with Fernandina Beach and St. Augustine reflecting colonial periods and Key West showcasing the fun side of Floridians. Different districts offer separate things to do, adding to the excitement of touring the Sunshine State. Those looking for a laid-back coastal time should consider Siesta Key or Venice, while antiquers will love Micanopy. Florida is known for many things, and visiting these 12 Main Streets is a summation of what makes Florida so unique.
