Last Updated May 10, 2021 5/10/2021

11 Most Picturesque Small Towns in Florida

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Florida is known for its tourist-packed theme parks and white sand beaches, however, outside of these destinations lie quaint towns full of rich history, unique charm, and hidden gem beaches that are worth exploring. For a memorable off-the-beaten-path journey, check out some of these lesser-known picturesque towns you can visit in Florida.

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Mount Dora
Mount Dora

Mount Dora

One of the more popular small towns in Florida, Mount Dora boasts 19th-century clapboard houses and historic buildings amongst antique shops and outdoor cafes. Stroll along the quaint downtown shops and soak in a classic glimpse of Old Florida.

Amelia Island
Fernandina Beach on Amelia Island

Amelia Island

Spanish moss, quaint B&B’s, and pristine beaches make up this island on Florida’s northernmost eastern border. Full of southern charm, the historic downtown, delightful shops and restaurants, and beloved Fernandina Beach earns Amelia Island a spot on this list.

Apalachicola
Apalachicola

Apalachicola

A friendly little fishing town, Apalachicola is a Florida gem that boasts some of the best seafood and friendliest locals in the state. Visit the nearby St. George Island, go on a river cruise, or try your hand at fishing like the locals.

Anna Maria Island
Anna Maria Island

Anna Maria Island

With speed limits that never reach higher than 35 mph, this quaint 7-mile barrier island is full of cyclists, kayakers, and turquoise water views. Only 50 miles south of Tampa, visit Anna Maria for laid-back vibes and picturesque natural scenery.

St. Augustine
St. Augustine, Florida

St. Augustine

While America’s oldest city has become quite popular throughout the years, it has continued to maintain its small-town vibe and historic authenticity. Explore the quaint Spanish colonial architecture, peaceful Crescent Beach, or visit the oldest masonry fort in the U.S.

Tarpon Springs
Tarpon Springs

Tarpon Springs

You will find old world charm in this small town near its bustling neighbor Tampa. Visitors love Tarpon Springs for its heavily influenced Greek culture, scenic waterfront, and eclectic mix of antique stores and art galleries.

Santa Rosa Beach
Aerial View of Breaking Waves at Santa Rosa Beach Florida

Santa Rosa Beach

Situated on Florida’s Emerald Coast you will find 26 miles of white powdery sandy beaches, luxury beach houses, and pristine scenic landscapes. At this top beach destination in Florida’s Panhandle, you can visit Topsail Hill Preserve State Park, the unique artist colony Gulf Place, or Point Washington State Forest’s 15,000-acre preserve.

Destin
Destin, Florida

Destin

Breathtaking and scenic, Destin is the “world’s luckiest fishing village,” allowing fishermen to easily access the deepest waters of the Gulf of Mexico, and deep waters means a variety of fish species. After a day on the water, set up camp at Henderson Beach State Park, walk along the action-packed boardwalk, or visit historic Fort Pickens.

Sanibel Island
Bowman's beach at Sanibel Island

Sanibel Island

Located along the Gulf of Mexico, Sanibel is an easy-going town popular for shelling, stunning sunsets, and laid-back vibes. Devoid of fast-food restaurants, street lights, and city noise, Sanibel maintains its cozy small-town vibe.

Brooksville
Weeki Wachee

Brooksville

Brooksville is known for being both historic and charming, with moss-laden oak trees, canopy roads and rolling green hills. Home to the nearby pristine spring waters of Weeki Wachee and immaculate trails in Withlacoochee State Forest, Brooksville is a lesser-traveled vacation destination.

Winter Park
Winter Park Farmers Market

Winter Park

A hub of cultural activity, Winter Park is home to local arts and music festivals. Explore the historic sites of Casa Feliz, shop along Park Avenue, or soak in the natural beauty at one of its gorgeous parks and gardens.

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