10 Standout Main Streets In Florida
Florida is well known for its tourist destinations, tropical beaches, and towns with retro character. These standout Florida Main Streets capture the best of the Sunshine State, offering lively entertainment, laid-back getaways, and plenty of history in walkable districts. Each one reflects the region's past while also feeling current and welcoming, which keeps visitors coming back year after year. We've included coastal and inland towns; take your pick. You'll find that any of them can give you a more personalized and memorable experience than any cookie-cutter tourist resort. So put on your coolest shades and sunscreen and get ready to check these off your bucket list.
St. Augustine
Historic Saint Augustine, often described as the oldest continuously occupied European-established settlement in the continental United States, is a walkable area with compact streets that revolve around St. George Street. The pedestrian-only road is the main strip, lined with centuries-old buildings and numerous historic sites, including the purported "Oldest Wooden Schoolhouse." The historic district also features modern shops and fun places to grab a drink, such as the St. George Tavern, which is popular among both locals and visitors.
Strolling through the cobblestone streets and Spanish buildings gives a sense of awe, and little has changed on these roads over the centuries. However, there are plenty of modern conveniences on or near St. George Street, such as the well-known White Lion Bar and Grill, which offers outdoor seating with views of the Castillo de San Marcos. Behind the restaurant is the Agustin Inn, a cozy bed and breakfast located in the center of the district, and a perfect base for exploring the area or simply relaxing, however the mood strikes you.
Fernandina Beach
Downtown Fernandina Beach's main thoroughfare is Centre Street, where pedestrians are greeted by a mix of Spanish, French, and other architectural styles. Known as the Isle of Eight Flags, this fun north Florida town has been ruled by eight separate governments, giving it a fusion culture that is hard to pass up on this coast. The Palace Saloon advertises as the oldest bar in Florida. Hola! Cuban Cafe is another downtown local staple that reflects the city's cultural heritage and the community's affection for regional cuisine and high-quality coffee. Victorian homes line the commercial district, many of which have been converted into inns, including the Florida House Inn. Just off Centre Street, the 1857 inn is often described as the longest continuously operating hotel in the state of Florida. Altogether, walking Centre Street is a bit like going forward in space, but back in time.
Apalachicola
Historic Apalachicola was built around several town squares that today serve as the main arteries of the fishing village. It sits on Florida's Forgotten Coast, a lightly developed stretch of the state's eastern Panhandle known for its laid-back, old-Florida vibe rather than big resort crowds. Along Market Street and the surrounding blocks, the historic downtown district, promoted by Apalachicola Main Street, is an amalgamation of art, history, and cultural finds, such as the Dixie Theatre. The theater, built in 1912, continues to serve as a community gathering spot for locals and visitors.
One of the seaport's most notable claims to fame is its oysters, which have been a key economic driver since the town's founding. No trip is complete without sampling the local fare that brings people from all around the world. Downtown restaurants like Apalachicola Seafood Grill and The Station Raw Bar are two options. For those looking for a pick-me-up, Cafe Con Leche is an excellent choice for coffee. Like it black? Just ask for it “sin leche.”
Cedar Key
On Florida’s Nature Coast, a quiet stretch of Gulf shoreline known for small towns and wild marshes, Cedar Key is a vintage town that embodies the classic “old Florida” mystique. Dock Street is the de facto Main Street, a waterfront street with wide gulf views that doubles as the village's communal hub. The island community reflects the true spirit of the Sunshine State, and its history can be explored at museums like the Cedar Key Historical Society Museum, which offers a closer look at island life. One of the easiest ways to get to know Cedar Key is through its seafood. Tony's Chowder House is famous for its clam chowder, while Steamers Clam Bar and Grill serves fresh Gulf catches with wide water views. Both keep things relaxed and low-key, a perfect match for this laid-back island town.
Tarpon Springs
The definitive Grecian fishing village of Tarpon Springs is an ideal destination for discovering “old Florida” while enjoying modern amenities. Dodecanese Boulevard is the main artery through town and a hub of activity, lined with Greek bakeries, markets, and landmark eateries like Mykonos that grew out of the community founded by Greek sponge divers in the early 1900s.
Today, visitors can still stroll the historic sponge docks and the old Sponge Exchange, where fishermen once brought in their haul and which now houses shops and boutiques like My Little Black Dress. A classic cigar shop, Serafin de Cuba, also has a home here, but it’s the town’s Greek heritage and sponge-diving history that truly define its character.
Key West
The party scene in Key West revolves around Duval Street, where a vibrant mix of bars, museums, and a lively atmosphere greets visitors. World-famous Sloppy Joe's Bar was a favorite hangout of Hemingway and a must-visit destination for those seeking cold beer, live music, and a memorable experience. This small island city is renowned for its inclusivity of people from all walks of life and for its diverse range of venues, including cultural attractions like the Red Barn Theatre. Dubbed "one of the best professional theaters in South Florida," it regularly hosts Broadway-caliber shows. The Key West Butterfly and Nature Conservatory has been voted a top destination in a town full of them by the People's Choice Awards. It is home to hundreds of butterflies that originate from around the world, as well as exotic birds. Of course, fishing is one of the major attractions in Key West. An easy walk from Duval Street, the Historic Seaport is the jumping-off point for Key West’s famous fishing charters.
Seaside
The New Urbanist-designed Seaside was created around its town center, a walkable district and the main attraction of the beach town, and home to many boutiques, such as Poeta. Central Square Records is a bookstore that also carries an extensive music selection, setting the tone for a day at the beach. The architectural styles and sunny weather are the calling cards of this village. It's so idyllic that it served as the main setting for the movie "The Truman Show," starring Jim Carrey.
There is no shortage of notable restaurants, including Bud & Alley's, a legendary beachfront establishment offering far-reaching sunset views and a local tradition for nearly four decades. Another well-known stop is Airstream Row, a collection of food trucks serving barbecue, ice cream, and more, perfect for a summer day in Florida. This town was intentionally designed for walking, making it the best way to experience its eclectic scene while enjoying a relaxing getaway.
Mount Dora
Mount Dora's historic section is home to many preserved homes, inns, and points of interest, as well as live events. A landmark is the 1883 Lakeside Inn, the state's longest continuously operating hotel, located just a short distance from many of the city's venues. Dubbed the "City of Festivals," Mount Dora hosts more than 30 annual festivals, like the Mount Dora Art Festival. This festival not only showcases over 300 artists, but it also provides food and entertainment, and is a great way to rub elbows with the locals. No matter the time of year, no one should pass up at least one meal at 1921 Mount Dora. Contemporary Florida cuisine reflects the best of the regional food scene and also focuses on techniques introduced by explorers and immigrants to the area.
DeLand
Downtown DeLand's Historic Garden District is an award-winning Florida Main Street community, one of the first to receive the designation in 1985. The DeLand Sculpture Walk and the Historic Mural Walk are just two ways to truly experience the district, which also introduces visitors to the various sites and venues lining its streets. Athens Theatre is another cultural icon in DeLand, one of a handful of classic performance theaters in central Florida. There are also many historic homes to discover, including the DeLand House. The historic home is open to the public and, during the Christmas season, is tastefully decorated to evoke the 1920s, offering guests a glimpse of the town's past. Nightlife is also an experience here, with places like The Elusive Grape featuring more than 40 wines and a pleasant way to end the day.
Venice
Historic downtown Venice dates to the 1920s and has classic Florida touches, along with many vintage hotels like Hotel Venice. The legendary inn is a Mediterranean Revival-style building that opened in 1926 and reverberates the creative flair and vibrancy the district is famous for. This is very much an outdoors community, a fact underscored by the active Centennial Park in the middle of downtown. Centennial Park is the place to be to catch a free concert and find local information at the Venice MainStreet kiosk for a self-guided tour. The Venice Train Depot offers a different look at the area's roots, including a vintage circus train and a video detailing its significance. Visiting these destinations while soaking in the Florida sun is one of the best ways to experience the state and discover its multifaceted history.
The Mystique of Florida
Florida has a storied history, and these standout streets echo this heritage while offering modern amenities for visitors, making them some of the most engaging places to visit in the state. Historical buildings are the norm in these tiny villages, and the architectural styles echo the various governments that have ruled the region at different periods. Downtown areas reflect the modern community with local shops and restaurants, adding to the mystique and giving travelers plenty to explore at an easy pace.
Tropical islands such as Key West sit alongside welcoming inland towns, and each region offers its own character, including historic inns that make for an authentic Florida getaway. History buffs are drawn to destinations like Apalachicola and St. Augustine, while beachcombers will not want to bypass Tarpon Springs. Tight-knit communities add to the appeal of these villages and hamlets, leaving visitors with an indelible impression of "old Florida" that makes for a memorable holiday.
