Most people picture beaches when they think of Fort Myers, but I discovered that the historic downtown showcases a completely different side of this beautiful corner of Southwest Florida. Get ready to be impressed by Fort Myers’ River District, where palm-tree-lined streets, brick roads, and historic buildings are now home to lively shops, restaurants, and bars.

Known as the “Land of Chiefs,” Chiefland sits along US 19 in Levy County and is much more than a place to simply pass through. The city and its surrounding areas have stunning natural springs, charming local shops, unique museums, and riverside dining that make it an easy and enjoyable day trip.

If you’re looking for a quiet corner of Old Florida, you’ll find it tucked along the Withlacoochee River in Levy County. Yankeetown is one of the smallest communities in the state, and it’s as peaceful, charming, and laid-back as they come.

Boca Grande, on the south end of Gasparilla Island in Lee County, takes some effort to get to because you don’t just pass through, you have to go there on purpose. And when you arrive, you’ll find an island community unlike anywhere else in Florida.

Jacksonville Beach is one of Florida’s cutest small surf towns. It’s full of character, local flavor, and ocean views that never get old. If you’re planning a visit, here are seven ways to make the most of a perfect day (and night!) in this coastal gem.

Just 30 minutes from Fort Myers, Pine Island is the largest island on Florida’s Gulf Coast, yet it still feels like a hidden gem. Unlike nearby Sanibel and Captiva, you won’t find sandy beaches here. Instead, you’ll discover mangrove shorelines, tropical fruit farms, and a resilient community dedicated to preserving Pine Island’s Old Florida charm.