Boca Grande

Located on Gasparilla Island, just north of the slightly better-known Sanibel and Captiva Islands, Boca Grande is the epitome of Old Florida charm. It’s got the turquoise waters and powdery white sands typical of Southwest Florida, but the town itself is still the selling point. The historic downtown has a wide main street with no stoplights, no billboards, and no fast-food chains. In their place are fresh seafood joints, boutique art galleries, and colorful convenience stores that sell ice cream alongside cigars.

Make sure to visit the restored lighthouse and snap a photo, dig into soft-shell crabs at Temptation, and rent a bike or golf cart to cruise down the abandoned-railroad-track-turned-tree-lined trail (part of Florida’s Rails-to-Trails Conservancy project).
If you’re up for a little more adventure, you can kayak or paddleboard through the pristine estuaries formed by the outlets of the Myakka and Peace Rivers. To see the tarpon congregate (you know, those giant silver fish people are always showing off in photos), take a boat across the Boca Grande Pass and cruise over to Cayo Costa State Park.