These 11 Towns in Florida Have The Best Main Streets
The best main streets reveal a town's true character in one glance, offering a balance of attractions without being overly touristy. In Florida, towns manage to provide just the right mix of culture and attractions to keep visitors intrigued but not overwhelmed. These towns are perfect for exploring, with ample opportunities to play, rest, and recharge.
From the quaint Key West to the larger town of Naples, each offers a unique and picturesque setting where you can relax, enjoy family fun, and indulge. Discover why Stuart is known as “America’s Happiest Seaside Town” on Florida’s Treasure Coast, or experience a slice of Greece along Tarpon Springs' Dodecanese Blvd.
DeLand
Located in the heart of the state, the historic city of DeLand is easy to access and memorable with its highly walkable downtown. New York Avenue, known for family favorites like the Haunted Antique Shop and Paranormal Museum, and the popular Freedom Playground, is lined with beautifully restored vintage buildings. At the intersection with Woodland Boulevard, you'll find the Florida Victorian Architectural Salvage from 1926, offering over 8,000 square feet of architectural treasures and epitomizing downtown's commitment to repurposing artifacts.
Adjacent to this, the area's only meadery, Abbey Bar, is part of the Cool Craft Trail. Nearby, Elusive Grape appeals to wine enthusiasts, while Persimmon Hollow and Hyderhead Brewery offer atmospheric evenings. This award-winning area boasts irresistible shops and dining for all tastes, ranging from adorable boutiques to vinyl record stores and antique shops, set against historic facades. In summer, visitors can swim with Florida's manatees at nearby Blue Spring State Park and enjoy annual festivities and outdoor markets.
Dunedin
Dunedin, or "Dùn Èideann" in Gaelic, meaning Edinburgh, is a charming town just north of Tampa and St. Petersburg. Known for its positive vibes and affordability, Dunedin has been dubbed the “Best Walkable Small Town” and is near “#1 Best Beach in America.” Its pedestrian-friendly Main Street is lined with colorful shops and restaurants, like the pet-friendly Our Place Dunedin. Families can enjoy rides on the Jolley Trolley trams and visit the Art from the Heart Cafe.
As a town first settled by Scots in 1852, Dunedin celebrates its Scottish heritage. Roads like Keene Road and Achieva Way, along with various eateries and pubs, reflect this heritage. The town's old-country vibe is enhanced by cultural events and festivals, such as the Dunedin Celtic Music Festival and the Craft Beer Festival, which immerse the town in Scottish traditions, complete with music, food, and craft beer.
Fernandina Beach
Imbued with Old-Florida charm and tropical allure, Fernandina Beach on Amelia Island offers a mix of big city amenities and spectacular beaches. It's a magnet for photographers, Instagrammers, and holidaymakers seeking a vibrant atmosphere. The family-friendly Central Street, stretching from the Amelia Island Welcome Center, past Central Park, to the picturesque waterfront along Atlantic Avenue, is a delight for visitors. Overlooking the Amelia River, Fernandina Harbour Marina provides a gateway for boating enthusiasts to explore the Intracoastal Waterway near the Florida-Georgia border.
The town's walkable downtown features a plethora of shops and restaurants housed in historic buildings. Notably, The Palace Saloon, established in 1903 by Adolphus Busch, founder of Anheuser-Busch, is the oldest continually operating bar in Florida and a popular nightlife destination. The Nassau County Courthouse, an architectural gem from the late 19th century, remains active with judicial and governmental affairs. Additionally, the Lesesne House, dating back to 1860, stands as one of the state's finest examples of classic Revival-style architecture.
Key West
Key West, the southernmost point in the continental US, is a city where everyday feels like a celebration. Originally named Cayo Hueso by the Spanish, meaning "Bone Islet," due to the discovery of human bones, it has retained its charm through various historical events, including battles against pirates and a devastating fire in 1886. Duval Street, the heart of Key West, is lined with historical buildings, restaurants, and shops, each reflecting the season's spirit. It's a short walk from the crystal-clear waters ideal for scuba diving, sailing, and snorkeling.
This palm-lined main street draws artists, writers, and families seeking inspiration amidst its unique architecture, modern attractions, and conch-style houses. Reflecting a fusion of Cuban, West Indian, Bahamian, and American cultures, Key West has attracted notable figures like Ernest Hemingway and Tennessee Williams. The downtown area, rich in tropical ambiance, leads to a sun-kissed coastline. The island, known for its 19th-century wooden homes once inhabited by writers, bursts into life every July with the Hemingway Days Festival, a celebration of its literary heritage.
Micanopy
Nestled just 10 miles south of Gainesville, Micanopy is a quaint town steeped in charm and history. As it approaches its 203rd anniversary, Micanopy is celebrated as one of Florida's hidden gems. Its main street offers a tranquil escape, easily accessible via the renowned S.R. 441, which passes through Paynes Prairie Preserve State Park and is famously mentioned in Tom Petty and the Heartbreakers’ song "American Girl."
Cholokka Boulevard, the heart of Micanopy, radiates quintessential Old Florida energy. Visitors can start their day with coffee and pastries at notable spots like Mosswood Farm Store and Bake House. The street is perfect for leisurely strolls, featuring architectural marvels and artisan shops ideal for finding unique gifts, books, and home decor. Lined with antique shops, cafes, bakeries, restaurants, and galleries, the boulevard is shaded by majestic oak trees draped in Spanish moss, offering a serene environment for relaxation and exploration.
Mount Dora
Situated beside two scenic lakes, Mount Dora is a picturesque town in Central Florida that captivates visitors with its historic charm. The historic downtown, especially along North Donnelly Street, is a hub for local events and features quaint shops. The town bursts into life during the Mount Dora Spring Festival, with celebrations extending to the lakeshores. The Mount Dora Historic District exudes small-town allure, with historic sites like the Goblin Market Restaurant & Lounge and the Lakeside Inn, which has been operational since 1883, nestled among other 19th-century buildings.
Mount Dora's vibrant art scene, showcased in downtown galleries, studios, and festivals, is a highlight on the state's antique trail, which includes the famous Renninger’s Flea Market and Antique Center. Local eateries offer a variety of dining experiences, from casual to fine dining, with farm-fresh cuisine from the surrounding area. Notable establishments include The Frog and Monkey Restaurant & Pub and Copacabana Cuban Café. Outdoor activities abound, with opportunities to explore Lake Dora, known as the “Bass Capital of the World,” by pontoon boat or catboat, set against a backdrop of lush greenery.
Naples
Founded in the 1880s, Naples is a town in southwestern Florida, situated along the Gulf of Mexico. Contrary to the idea of being a destination for Italian immigrants, Naples is actually a cultural hub on the Paradise Coast, drawing families and retirees with its tropically infused atmosphere. The vibrant downtown showcases historic architecture, and the town is renowned for its miles of sugar-sand beaches and a popular fishing pier. Key areas include Broad Avenue, stretching from shore to shore, and Gulf Shore Boulevard by the waterfront, while Third Street hosts numerous venues.
Naples, known for its lively events on Fifth Street, is home to Victoria Park, featuring hundreds of beautifully decorated homes, a highlight in Southwest Florida. The intersection of Third and Fifth Streets is a bustling area with upscale shops, bars, and restaurants, including Italian-style patio cafes perfect for people-watching. The heart of Naples offers the lush Caribbean Gardens and Zoo, providing a refreshing escape. Additionally, the nearby 5-acre Collier County Museum, an open-air historical park, enriches the cultural experience.
Pensacola
Pensacola, known as America’s first settlement, boasts a rich history. The town is adorned with old-growth moss-covered oak trees and crepe myrtles, complementing its Spanish-influenced architectural grandeur. Palafox Street, the main thoroughfare, is ideal for exploring the town, even during a brief visit. Starting from the parking lot near Palafox Pier and Plaza de Luna, visitors can enjoy a coffee while overlooking the bustling Port of Pensacola and Pensacola Bay. The marina and shipyard are highlighted by the imposing bronze statue of the Spanish explorer, Don Tristán de Luna y Arellano.
The town has transformed its historical saloons and brothels into a hub of locally-flavored restaurants and bars. Highlights include Restaurant IRON and the Old Hickory Whiskey Bar. While exploring, don't miss historic Plaza Ferdinand and Seville Square, as well as museums and unique shops like Bubba’s Sweet Spot, Bodacious Brew, and Carmen’s Lunch Bar & Tapas. Currently adorned for Winterfest, the celebrations radiate from the corner of Government Street and Palafox Place, featuring shows, live music, carriage rides, and Santa's Holiday Express.
St. Augustine
St. Augustine, the nation's oldest continuously settled city, was founded by the Spaniards in 1565, though they first landed in search of the legendary Fountain of Youth in 1513. This historic city is known for its centuries-old architecture, showcasing Moorish and Spanish colonial styles in its Historic District. St. Augustine, with its intricate blend of modern and cultural elements, stands as one of the most aesthetically rich towns in the United States. The Castillo de San Marcos, a symbol of the Spanish Empire and the oldest masonry fort in the United States, was built between 1672 and 1695.
This national monument, located near the southern tip of the peninsula, gives St. Marcos Ave., the main street, its name. The street is lined with restored Spanish colonial buildings and sites. The town's multicultural thoroughfare maintains its historic charm, complete with Old Town trolleys and quaint street cafés. Must-visit sites include the Lightner Museum, the St. Augustine Lighthouse and Museum, and the Government House Museum. Be sure to explore the hidden courtyards, which offer a serene glimpse into the town's 500-year history.
Stuart
Stuart, known as “America’s Happiest Seaside Town” on Florida’s Treasure Coast, is renowned for its historic riverfront downtown. This area offers a delightful dining and drinking experience, complemented by over a dozen murals that showcase Stuart’s unique character. The Sailfish Marker trail takes visitors through Stuart’s rich history, passing landmarks such as the Court House Cultural Center and the Stuart Feed Store Museum. At the waterfront end of Seminole Street lies the Riverwalk Stage.
Just steps away from the St. Lucie River, the Riverwalk boardwalk stretches from the docks of Sunset Bay Marina to the historic homes on Seminole Street. Visitors can explore over 50 locally owned shops, restaurants, and galleries nestled among turn-of-the-century buildings, with history at every turn. Stuart offers a variety of attractions, from beaches along Ocean Boulevard (Hwy A1A) to year-round live entertainment. Notable venues include the Lyric Theatre, beautifully restored from its 1926 origins on Flagler Avenue, and the Geoffrey C. Smith Gallery on Osceola Street, home to fine art and the iconic Stuart Sailfish statue.
Tarpon Springs
Located just 45 minutes north of St. Petersburg, Tarpon Springs is a showcase of Greek Revival elegance set against the picturesque backdrop of the Gulf of Mexico. Named for the abundance of tarpon fish in the area, Tarpon Springs is renowned as the "sponge capital of the world" and has a downtown area listed on the National Register of Historic Places. As the town with the most pronounced Greek heritage for hundreds of miles, the influence of Greek settlers is evident in its traditions, architecture, and cuisine, offering some of the best Mediterranean food in the region.
The town's commercial areas, marked by now-whitewashed buildings, house art galleries, antique stores, and specialty shops. Historic markets have evolved into vibrant spaces selling a variety of goods. The Greek heritage, combined with 51 miles of waterfront, draws visitors to stroll along the brick streets of the Historic District's Dodecanese Blvd. and other quaint, winding streets. From stores selling natural sponges to historic architecture dating back to the late 1800s, the Tarpon Springs Performing Arts and Cultural Center is a hub for theater, art exhibitions, and concerts.
Exploring New Towns
Discovering a new town can be overwhelming with so much to see and do, but don't let that deter you from visiting one of these 11 towns in Florida. Each town embodies the heart and soul of the state, with main streets that pulse with life and character.
There’s nothing quite like wandering through local mom-and-pop shops in the downtown area, whether you're shopping or dining. Once you venture beyond the main thoroughfare, you’ll find yourself eager to explore further, often discovering splendid waterfronts and historic landmarks. A prime example is St. Augustine's grand Castillo de San Marcos, a testament to the rich history found in these Floridian towns.
