11 Picture-Perfect Main Streets In Florida

The whitewashed fence Tom Sawyer's friends painted still stands in one Florida town, and it is not the only main street here still in everyday use. Fernandina Beach and Tarpon Springs still have their Victorian storefronts in service. Spanish colonists cut the coquina blocks pedestrians still pass in St. Augustine. A cafe row lines the live oaks of Winter Park; an old citrus-and-rail downtown now holds a market district in Winter Garden. None of it was staged. Each block earned its look over a century of ordinary use.

Mount Dora

Donnelly Street runs along a freshwater bluff above Lake Dora, a rare bit of elevation in central Florida that opens wide water views between the 19th-century rooflines. The 1893 Queen Anne-style Donnelly House, painted yellow and white, is the landmark on the main drag, and its owners run seasonal ghost tours and paranormal investigations on-site. Donnelly Park sits directly across the street, a break in the storefront row with a fountain and pickleball courts under mature shade trees.

Downhill in the retail block, Several vendors share one roof at Mount Dora Marketplace, where communal tables fill up over made-from-scratch crepes, Lebanese dishes, and flavored mimosas. A few steps toward 4th Avenue, the Modernism Museum holds a collection of studio furniture and American decorative art in its galleries, including pieces by Wendell Castle and Wharton Esherick.

Key West

Few streets in the country touch two seas, but Duval Street does it in just over 1.25 miles, from the Gulf of Mexico at one end to the Atlantic at the other. Near the Gulf end sits Sloppy Joe's Bar, which traded on its reputation as Ernest Hemingway's favorite hangout in the 1930s and still pours a citrus-forward tequila cocktail called the Sloppy Rita. A block south, the Oldest House Museum & Garden occupies an 1829 Bahamian-style conch cottage filled with maritime artifacts and historical artwork. Behind it stand the oldest surviving cookhouse in Key West and a tropical garden planted with Spanish lime trees.

Farther south, the Key West Butterfly and Nature Conservatory is home to more than 50 butterfly species inside a climate-controlled glass dome, where flamingos wander the paths at will. The street runs out at South Beach, a 200-foot arc of sand along the Atlantic with a short pier where swimmers can jump in.

Naples

Arched windows, red-tile roofs, and rows of royal palms give Fifth Avenue South its Mediterranean look, and the avenue runs straight toward the Gulf of Mexico about two hours west of Miami across the Everglades. The same Mediterranean look continues at Osteria Tulia, a Sicilian kitchen known for wood-fired Neapolitan pizzas and handmade pastas. Toward the beach, the Naples Players stage dramas and comedies at the Sugden Community Theatre, which has two indoor stages and an outdoor community stage. A block over, Cambier Park is 12 acres of green space along the avenue, with the Naples Art Institute's gallery set among the trees.

Near the far end of the street, the Naples Depot Museum documents how the railroad turned Naples into a resort city. Restored railroad cars, an antique swamp buggy, and a mule-drawn wagon are among the pieces on display.

Fernandina Beach

Eight blocks of Victorian-era facades and cast-iron gas lamps line Centre Street as it slopes toward the Amelia River. The 1891 Nassau County Courthouse stands on the high ground with its bell and clock tower, an Italianate design with arched windows and Corinthian columns worth a look from the sidewalk. One block on, more than 35 dealers set up inside the Eight Flags Antique Market.

Centre Street ends at the Fernandina Harbor Marina, where wooden boardwalks open onto views of commercial shrimp trawlers and wild Atlantic bottlenose dolphins. The Palace Saloon sits at the end of the walk, billed as the oldest continuously operating bar in Florida since 1903. Regulars order the Pirate's Punch, a potent rum mix made to a guarded recipe.

Winter Park

About seven miles north of Orlando, Park Avenue runs beneath towering live oaks past European-style cafes and blooming rose gardens. Central Park is the anchor, an 11-acre green with moss-draped trees and decorative fountains, and the Charles Hosmer Morse Museum of American Art stands just steps from the park greens. Its collection is built around Louis Comfort Tiffany, from a restored chapel to reconstructed living spaces with glass lamps and stained-glass windows.

Docents lead tours through Casa Feliz, an Andalusian-style house with courtyard gardens, original artwork, and 1930s furniture in its rooms. The walk ends at The Wine Room on Park Avenue, where a self-pour system dispenses samples from more than 150 bottles by the ounce.

Winter Garden

Half an hour or so from Winter Park, Winter Garden has a blue-collar downtown built on citrus and rail rather than a European-style promenade. The West Orange Trail runs straight down the median of Plant Street, a 22-mile paved path laid over an abandoned railroad alignment that puts the whole downtown within easy reach. Inside Plant Street Market, more than 20 vendors and food artisans sell handmade goods and organic foods from stalls under one roof.

Local entertainment runs out of the Garden Theatre, with professional stage plays, live music, and classic film screenings on its calendar. A few doors down, the Winter Garden Heritage Museum occupies a 1918 Atlantic Coast Line train depot, where the exhibits run from vintage citrus crate labels to railroad memorabilia.

Micanopy

Spanish moss hangs in a near-continuous canopy over Cholokka Boulevard, shading a row of weathered 19th-century storefronts in Florida's oldest inland town. At the north end, an 1845 farmhouse later encased in brick and remade in Greek Revival style now operates as the Herlong Mansion, a three-story inn with thirteen rooms and complimentary homemade breakfasts. Beulah Franklin Park faces it across the street, a green pocket with a white gazebo and grassy lawns.

Down the shaded corridor, the Micanopy Historical Society Museum occupies the former Thrasher Warehouse, its local artifacts including an 18-foot Indian wooden canoe, displays on the Seminole Wars, and a set of frontier farming tools. A few minutes down the road, Antique City Mall packs rare collectibles and vintage decor into a 20,000-square-foot space, part of the reason Micanopy is known as a Florida antiques capital.

Dunedin

Pastel storefronts, outdoor dining patios, and Scottish tartan banners flank Dunedin's Main Street as it runs toward St. Joseph Sound. The paved Fred Marquis Pinellas Trail cuts through downtown here, a multi-use route of roughly 45 miles that reaches St. Petersburg at one end and Tarpon Springs at the other. Right along the trail, the Dunedin History Museum sits inside a restored train depot, its galleries packed with century-old railroad equipment, Scottish heritage artifacts, and citrus-crate labels.

Caledonia Brewing sits inside the old Dunedin Times newspaper building, where the signature Rat Arsed Scottish Ale takes its name from the town's Scottish roots. Main Street finishes at Edgewater Park, four acres of shaded waterfront beside Dunedin Marina with a nautical-themed playground and a Centennial Tree planted to mark the town's 100th year in 1999.

Tarpon Springs

Five miles up the coast from Dunedin, Tarpon Springs has a main street rooted in Victorian Florida and the railroad boom. Tarpon Avenue begins at Spring Bayou, a spring-fed lake ringed by historic mansions and tall trees where wild manatees gather in the cooler months. Away from the water, the Replay Museum is home to more than a hundred restored pinball tables and arcade cabinets, and a single ticket buys unlimited play on every machine.

The 1909 Atlantic Coast Line station now holds the Tarpon Springs Historical Train Depot Museum, whose exhibits trace the railroad that built the town, down to antique ticketing systems and vintage conductor uniforms. Tarpon Springs Castle Winery is a fitting last stop, with hand-crafted wines to sample inside a European-style tasting room or out in the courtyard.

St. Augustine

Foot traffic has the run of St. George Street, the pedestrian-only spine of St. Augustine, the oldest city in the United States. The Old City Gate marks the northern end, a coquina landmark that once controlled the only way into the fortified city. At the southern end lies the Plaza de la Constitucion, laid out in 1573 and still hosting free summer concerts and open-air markets.

Between them, the Colonial Quarter is a two-acre recreation of Spanish and British colonial life, with costumed experts working early trades like blacksmithing and a 35-foot wooden tower rising over the shops and restaurants around it. Come dinnertime, Prohibition Kitchen lets guests mix their own Old Fashioned or build their own burger in a speakeasy-inspired hall with booths on the lower level and a balcony over the stage, where live music plays most nights.

DeLand

Wide brick sidewalks, cast-iron streetlamps, and 19th-century storefronts set the tone along Woodland Boulevard in downtown DeLand. The Museum of Art - DeLand is a gallery of modern American paintings, sculpture, and rotating national exhibits. Farther south, the Muse Book Shop lines its floor-to-ceiling wooden shelves with new releases, used paperbacks, and a section given over to Florida history.

At the north end of the strip, the Stetson University campus stays open to the public, with 19th-century brick architecture and landscaped lawns shaded by broad live oaks. For more open ground, Pioneer Park is a small downtown green with a mural, a water fountain, and picnic tables.

Working Downtowns, Not Backdrops

What ties these eleven streets together is that people still use them for the ordinary business of a town. Courthouses process civic work, theaters book their seasons, and century-old storefronts hold independent shops rather than museum labels. The Spanish colonial coquina of St. Augustine, the Scottish tartan of Dunedin, and the Victorian rooflines of Fernandina Beach each grew out of who settled where, which is why no two of these main streets read quite the same.