Best 8 Small Towns in Florida Have More Charm Than We Can Handle

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Anna Maria Island

Experience timeless charm on this barrier island with seven miles of white sand beaches. Explore antique shops, galleries, and seafood restaurants. Enjoy the City Pier and free trolley.

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Fernandina Beach

Discover 13 miles of pristine beaches on Amelia Island's northeast coast. Visit during the Isle of Eight Flags Shrimp Festival or enjoy golf, resorts, and quaint shops year-round.

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Apalachicola

Enjoy fresh seafood in this panhandle town. Stay at The Gibson Inn and explore oyster history or relax on St. George's Island's pristine beaches.

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Rosemary Beach

Find a hidden gem on Scenic Highway 30A. Enjoy peaceful beaches and European vibes on Main Street in this charming town.

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Seaside

Experience a car-free, bike-friendly town in northwest Florida. Named Florida's prettiest town, it offers quaint cafes, food vendors, and sugar-white sand beaches.

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Winter Park

Just north of Orlando, this cultural hub features Rollins College and The Charles Hosmer Morse Museum. Enjoy upscale shopping, dining, and parks in its walkable downtown.

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Naples

Perfect for retirees, Naples boasts pristine beaches and charming neighborhoods. Stroll Third Street South for shops, bistros, and fountains, or explore upscale Fifth Avenue.

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Crystal River

Swim with manatees in this central Florida town. The constant 72-degree waters of Three Sisters Springs make it a haven for these gentle giants.