9 Best Downtowns In Florida
Florida’s best downtowns were engineered for people to stay around, with their broad porches and streets laid out for evening breezes off lakes, rivers, and the Gulf. Some grew from the 1920s building boom, when Mediterranean Revival storefronts and garden districts became civic pride projects. Others were designed with bold geometry—Sebring’s famous circle is a rare American town plan inspired by ancient models.
Along the way, a former bank becomes an artisan hall, a Victorian inn anchors a harbor stroll, and a working theater keeps its marquee lit decade after decade. These nine downtowns reward slow walking and open curiosity, where history sits in plain sight and today’s fun feels woven in. Even in winter, patios stay busy.
Clermont
40 minutes west of bustling Orlando, the charming lake town of Clermont offers a much-needed escape from the busy theme parks and resorts. This central Florida town was founded in 1884 between two lakes: Lake Minneola to the north and Lake Minnehaha to the south. With countless attractions just a stone's throw away from Lake Minneola, historic downtown Clermont is a charming alternative to Orlando’s flashy downtown.
A breezy 5-minute walk from the lake will bring you to one of Clermont’s best features, the Downtown Exchange. Originally built in the early 1900s, what was once the First State Bank has since been restored into an artisan market. Local vendors include gems like the Clermont Mini Bar, the Healthy Nut Cafe, Triangle Vinyl, and the Cookie Queen Factory.
From there, it is easy to explore Clermont’s other downtown attractions, such as the Clermont Historic Village Museum, The Station—a lively bar and live-music venue in the former Clermont Brewing Company space—and waterfront restaurants like Salt Shack on the Lake. After a day of shopping, dining, and museum-hopping, Clermont’s Lake Apopka Trail and Waterfront Park are the perfect follow-up.
DeLand
To understand why DeLand is famous for its “Award Winning Main Street,” we have to look back in time. Once named “Persimmon Hollow” for the area’s wild persimmon trees, DeLand’s current name comes from the baking soda magnate who founded the town in 1876. While no longer known for its persimmons, you will find Deland’s modern streets brightened with a fabulous range of old oak trees planted back in the 19th century during a tax break campaign.
Following this beautification initiative, DeLand’s downtown continued to thrive into the 1920s, when sidewalks were constructed along with gorgeous displays of Mediterranean Revival Style architecture. Today, landmarks like the restored Athens Theatre attest to the town’s vibrant Roaring Twenties past. These efforts continued in 2001 when urban designer Michael E. Arth devoted 8 years to revitalizing 27 historic structures, producing Downtown DeLand's breathtaking Historic Garden District.
In addition to quaint locales like the Boston Coffeehouse and Nancy's Vintage and Retro, art, history, and preservation are the heart and soul of DeLand’s downtown. Heritage museums and outdoor exhibits are in high supply, with highlights like the Stetson Mansion, the Historic Mural Walk, and the DeLand House Museum, which is presently undergoing restoration as part of ongoing preservation efforts. An artistic spirit thrives here as well, showcased in venues like the DeLand Museum of Art and African American Museum of the Arts.
St. Augustine
For the ultimate trip back in time, St. Augustine is home to one of the best historic downtowns in the country. With buildings dating back to the 1700s, St. Augustine’s historic district has more than 20 sites recognized by the National Register of Historic Places, including the Ximenez-Fatio House, Alcazar Hotel, and The Cathedral Basilica of St. Augustine.
As with other historic towns, St. Augustine’s museums take center stage. The Villa Zorayda Museum is an opulent 1883 villa inspired by a 12th-century Moorish castle, standing in striking contrast to the Lightner Museum. This second museum houses Gilded Age antiques in the former Alcazar Hotel, a stunning Spanish Renaissance Revival building. The Governor's House Cultural Center and Museum is another top attraction, parts of it dating back to St. Augustine's Spanish colonial period.
For a more family-friendly experience, the St. Augustine Pirate & Treasure Museum is engaging for all ages. There is also plenty else to see and do in downtown St. Augustine as far as restaurants and attractions. Some of its best downtown eateries include Harry's Seafood Bar & Grille, Casa Maya, and the historic Columbia Restaurant on St. George Street, all within an easy walk of the bayfront. With the waterfront a short walk away, attractions like Ripley's Bayfront Mini Golf and St. Augustine Scenic Cruises can also be enjoyed right from downtown.
Sebring
Over in Highlands County, Sebring is an underrated Florida community whose downtown is anchored by a stunning lakefront. But what truly sets downtown Sebring apart is its design, inspired by the ancient Egyptian city of Heliopolis. Known as the "The City on the Circle," Sebring’s circular town center once intrigued investors and business owners, inspiring them to help develop the town in the 1920s. While Sebring has since been modernized in many ways, this quirky layout remains the town’s focal point.
As a designated 1920s Historic District, downtown Sebring provides a captivating glimpse into life during this iconic era. Notable landmarks such as the Circle Theatre (which first opened its doors in 1923) once showcased silent films and now serves as a vibrant live music venue. For those looking to immerse themselves in history overnight or simply enjoy another historic site, the Roanoke Hotel is an authentic slice of the past. Opened in 1917, this boutique hotel has since been beautifully restored to reflect its original grandeur.
Amidst the historic charms, downtown Sebring is brimming with modern attractions. Amidst the historic charms, downtown Sebring is brimming with modern attractions, from independent boutiques around the Circle to fun stops like Sebring Soda & Ice Cream Works, where shelves are lined with hundreds of vintage sodas and sweet treats. With beautiful Lake Jackson right next to Circle Drive, scenic sites like the Lake Jackson Fishing Pier are also within reach.
Mount Dora
Mount Dora’s waterfront is equally serene, with lake recreation mere steps away from its downtown attractions. The Mount Dora Dock and CatBoat Adventure Tours are great ways to experience beautiful Lake Dora, the town’s namesake. But back on land, Mount Dora’s blend of historic and modern charms are where its downtown truly shines.
Like other towns on this list, Mount Dora blossomed from the late 1800s to the 1920s. Today, the Mount Dora Historic District is a rich testament to the town’s heritage, with sites like the Donnelly House, built in 1893 in the Steamboat Gothic and Queen Anne styles. The self-guided Historic Mount Dora Walking Tour is also available for free on the Distrx mobile app, offering a narrated look at the town’s architecture.
Along with year-round attractions like the Modernism Museum, Sunset Park, and Donnelly Park, downtown Mount Dora is known for its spirited festivals. Every November, Light Up Mount Dora brightens the downtown with live music and holiday lights. The annual Mount Dora Arts Festival is equally uplifting, showcasing a range of talented artists with offerings of festival foods, music, and cocktails. On February 1st and 2nd, 2025, Mount Dora will celebrate the event’s 50th year.
Winter Garden
Located about 30 minutes south of Mount Dora, Winter Garden has one of the best downtowns in Florida. Along with landmarks like the historic Garden Theatre and SOBO Art Gallery, this cultural hub is renowned for its vibrant downtown events. But unlike Mount Dora, many of these events in Winter Garden take place year-round, making it easier for locals and visitors to take part in the fun.
Every Friday, the downtown Centennial Plaza Gazebo comes to life with live music, setting the scene as you enjoy the Winter Garden Fountain, clocktower, and surrounding shopping centers. On Saturdays, the town’s award-winning Winter Garden Farmers Market is another year-round charm, hosted at the Downtown Pavilion. With over 100 vendors offering everything from locally sourced produce to artwork and jewelry, the Winter Garden Farmers Market attracts a diverse crowd. It has been recognized as the “Best Farmers Market in the State of Florida and in the USA” several times by the American Farmland Trust, proving it to be well worth the hype.
Beyond the weekend, downtown Winter Garden is known for its vibrant shopping scene. With a “Walker’s Paradise” rating from WalkScore.com, visitors can window shop with ease, exploring the range of specialty shops and boutiques. Whether browsing for gifts at Apricot Lane Boutique, picking up a new read at Writer's Block Bookstore, or grabbing a sweet treat from Gingers Baking Company, downtown Winter Garden is the ultimate gateway to retail therapy.
Fernandina Beach
Walkability is equally important in downtown Fernandina Beach. Described as “Footloose & Car-Free,” this Amelia Island town was one of Florida’s first resort towns to prioritize walkability. Today, this model remains intact, allowing visitors to enjoy harbor views, shopping, and sightseeing all in one go.
Thanks to efforts supported by the Fernandina Beach Main Street Program, the downtown area has never looked better. The historic center offers a scenic area to explore, featuring landmarks like the Fairbanks House and Florida House Inn, both built during the Victorian era. Downtown also hosts popular attractions such as the Palace Saloon, Florida’s oldest bar. Nearby, you’ll find the Fernandina Harbor Marina, the Amelia Island Welcome Center, and Amelia River Cruises & Charters. To discover the area’s rich history, visit the Amelia Island Museum of History, located in a former county jail. The museum guides you through centuries, starting with the region’s first Indigenous residents. It also covers the French and Spanish explorers who settled here, the pirates who once raided the shores, and the Victorian-era homes that still line Fernandina Beach streets.
Key West
In beautiful Key West, eye-catching architecture is a signature of its historic downtown. Similar to St. Augustine, you will find a fabulous blend of Spanish colonial and Queen Anne Victorian styles, influenced by the town’s history of Spanish settlement and US acquisition. Landmarks like the Custom House, San Carlos Institute, and Ernest Hemingway House are among the most popular, transporting visitors to Old Florida.
Duval Street, often called the “main drag of downtown," is home to some of Key West’s top bars, museums, and activities. Whether you’re riding the Key West Old Town Trolley Tour or walking around, you'll discover spots like Sloppy Joe's Bar, Ocean Blue Galleries, and the Fury Key West Glass Bottom Boat excursion. Attractions such as the Key West Aquarium are perfect for families, while adults may enjoy bars like Hogs Breath Saloon or Green Parrot Bar.
Naples
For an elevated downtown experience, consider exploring the Gulf Coast town of Naples. Just a short stroll from Naples Beach and Naples Pier, the town center boasts a walkable district filled with a vibrant arts scene, high-end shopping, fine dining, and picturesque palm tree-lined streets. While the town’s white-sand shores are definitely the main lure for tourists, visitors agree that exploring its downtown is the perfect addition to any beach day.
On Fifth Avenue South, pedestrian-friendly walkways allow easy access to Naples’ artistic attractions such as the Sugden Community Theater, Shaw Gallery, Aldo Castillo Gallery, and Sheldon Fine Art. Meanwhile, Third Street South is better known for its luxury shopping and dining options, featuring over 65 stores and restaurants. Highlights include Charlotte Kellogg and Gattle's Fine Linens, with popular eateries like D'Amico's The Continental and Campiello, which are well regarded in the culinary scene. Overall, downtown Naples offers a refined combination of culture, shopping, and dining that boosts the appeal of this stunning coastal city.
Why Visit These Florida Downtowns?
While Florida’s beaches and theme parks remain the main attractions, its downtown areas hold a special appeal for many. For those interested in history, art, cafés, and fine dining, these districts truly shine. Whether you’re visiting Clermont as part of your Orlando trip or checking out downtown Naples after a beach day, these lively town centers with their unique attractions might inspire you to spend an entire vacation exploring Florida’s downtowns someday.
