The Best Small Towns in Florida Are Big on Charm
Get the best of both worlds with idyllic beaches and quaint downtown districts.
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The Sunshine State is known for big cities, like the glitzy metropolis of Miami and the bustling Orlando with all its Disney attractions. But it's also home to unique and special small towns—in case nightlife and rollercoasters aren't your thing. Escape to one of these destinations for a dreamy getaway, where you can relax, sure, but also try new activities, dine on delicious food, and shop til you drop. Think: New England and European charm—but with some of the most pristine beaches at your fingertips.
Want to feel like you're in Spain? Head to Pensacola. Italy? Venice, of course! French Riviera? Post up at Rosemary Beach, off of Scenic Highway 30A. We're talking brick-paved streets, old-school trolleys, lighthouses galore (photo ops, anyone?), pastel cottages, welcoming inns, cute cafes, vibrant Main Streets (New York isn't the only state with a Park Avenue!), and more. And almost all of these towns are just steps (or a bike ride) away from glorious white sand and brilliantly blue water.
While not all of these Florida destinations are technically small towns (some are neighborhoods within a city), we think you'll agree that they feel quaint, personal, and belong on this list. Which one are you booking first?
Anna Maria Island
Step back in time on this barrier island where strict regulations govern the type of buildings and businesses allowed. Situated between the Gulf of Mexico and Florida's main peninsula, Anna Maria features seven miles of white sand beaches. Its downtown offers antique retailers, galleries, and yummy seafood restaurants. Hop on the free trolley or stroll the wooden City Pier dating back to 1911.
Fernandina Beach
This Amelia Island enclave on Florida's northeastern border boasts 13 miles of pristine beaches. Visit during the May's Isle of Eight Flags Shrimp Festival or year-round for top-notch golf, upscale resorts, and adorable bed and breakfasts. A walkable downtown is popular for restaurants and shops, like decades-old Fernandina's Fantastic Fudge.
Apalachicola
This fishing town in Florida's panhandle is the place for fresh catch. Book a room at an inn (The Gibson Inn is cute) and learn about the local oyster, timber, and fishing history—or relax on miles of unspoiled beaches on nearby St. George's Island.
Rosemary Beach
Located off the famous Scenic Highway 30A is a hidden gem called Rosemary Beach. Come for the peaceful beach and stay for the European vibes on Main Street. (The Pearl Hotel is stunning, as you can see!)
Seaside
Leave the car behind in this walkable and bike-friendly town in northwest Florida—named the prettiest town in Florida by Architectural Digest. The setting for The Truman Show, its downtown offers quaint cafes, as well as food vendors in airstream trailers, just a stone's throw away from the sugar-white sand beach.
Winter Park
North of Orlando, this arts and culture community offers a small-town feel outside of Disney's hometown. Home to Rollins College and The Charles Hosmer Morse Museum of Natural Art, its walkable downtown is packed with restaurants, upscale shopping, and parks that play host to various events throughout the year.
Naples
It's no wonder retirees flock here. You get pristine beaches and picturesque neighborhoods that instantly feel like home. Blocks from the famous Naples Pier is Third Street South—where you'll find palm trees, pastel buildings, shops, bistros, fountains, and more. Naples even has an upscale Fifth Avenue of its own!
Crystal River
Swim with manatees in this central Florida town beloved by nature-seekers. The Three Sisters Springs flow at a constant 72 degrees, creating an ideal home for the gentle giants when the temperature drops in the Gulf of Mexico.
Palm Beach
Head to Palm Beach in South Florida if you want to feel a little fancy. (The Kennedys had a vacation home here.) Walk down Worth Avenue to find high-end boutiques, galleries, and restaurants, then take a tour of Whitehall, a Gilded Age mansion that's now open to the public.
Captiva
Sister to nearby Sanibel, this captivating isle on Florida's southwest coast offers biking, sailing, birding, and a variety of water activities. Its tropical topography of giant cacti and bougainvillea vines is a picturesque backdrop for the already stunning sunsets that attract visitors from far and wide.
Fort Myers
Make your way to the Fort Myers River District for the small-town feel you're craving, where brick-paved streets and historic buildings meet quintessential palm trees. Check the events schedule to catch one of the town's Art Walks (like flower displays in the business windows!) or Music Walks (local and regional musicians line the streets on the third Friday of the month).
Matlacha
Part fishing village and part artists' enclave, this quirky community over the bridge from Pine Island is quintessential old Florida. Enjoy the bohemian vibes by visiting shops, galleries, seafood markets, or hanging out at the community park.
Dunedin
One of the oldest towns on Florida's west coast, Dunedin features a walkable downtown, four miles of beach known as Honeymoon Island, and popular craft breweries—all about an hour from Tampa. The town's annual Scottish celebrations honor its heritage and history, as it was founded by two Scotsmen in 1899.
St. Augustine
On the northeast coast of Florida sits St. Augustine—the oldest city in the U.S. Known for its Spanish architecture and irresistible charm, you'll feel like you just hopped off a plane to Europe as you walk the cobblestone streets. Also, did someone say Fountain of Youth...?
Micanopy
Just 15 minutes south of Gainesville, this Seminole-named enclave features dozens of antique vendors on oak-lined Cholokka Boulevard. The annual Fall Harvest Festival brings music and crafts, but you can also escape the crowds in nearby Paynes Prairie Preserve State Park and watch wildlife from a 50-foot-high observation tower.
Boca Grande
Katharine Hepburn was known to vacation in this idyllic village off the Gulf Coast, on Gasparilla Island. Don't miss the Port Boca Grande Lighthouse and Museum—which is adorably adorned during the holidays.
Pensacola
Rivaling St. Augustine for the title of America's first European settlement (though St. Augustine is said to be the oldest continuously occupied city), Pensacola is teeming with Spanish-influenced architecture and restaurants. History buffs will want to stop by National Historic Landmark Plaza Ferdinand VII to see the precise spot where Florida was transferred from Spain to the U.S. in 1821.
Sanibel
Sanibel Island is known for being one of the best shelling beaches in the Sunshine State, because it sits perpendicular to the coastline. When you're not shell-hunting, visit the historic Sanibel Lighthouse or explore the quiet island by bike.
Mount Dora
Set on the shores of Lake Dora, an hour from Orlando, this "Bass Capital of the World" offers a more than 100-year-old historic village and a myriad of annual festivals. Book a room at a country inn or bed and breakfast and spend the day antiquing in the city center. Don't forget a photo op at the iconic lighthouse in Grantham Point Park.
Islamorada
Known as the "Sport Fishing Capital of the World," this slice of paradise sits 90 minutes south of Miami in the Florida Keys. Enjoy views of the aqua blue waters from its various bridges, fresh seafood at its many waterfront restaurants, and gorgeous sunrises at one of the piers.
Cristina Corvino is a senior editor for Hearst Magazines. A few of her favorite things include all things Christmas, cheese, coffee, and baseball. (Let’s go Mets!) She loves rewatching Gilmore Girls and Downton Abbey, and her favorite new(ish) shows are Ted Lasso and Trying. (Seriously, try it!)
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