Of all the rum-smuggling, treasure-plundering pirates to have set foot in southwest Florida, José Gaspar, better known as Gasparilla, is the most notorious. He set up his headquarters at Boca Grande on Gasparilla Island, so the story goes, where he built a palmetto palace and furnished it with the treasures he swiped from his high-seas adventures. Serious historians may doubt his existence, but Boca Grande continues to woo the great and the good who come to chase the glint of silver scales on the monstrous Atlantic tarpon that swim in its passes.
Despite its popularity as a blue-blooded bolt-hole, Boca Grande has a quaint fishing-village feel and is a great destination for families. It has miles of undeveloped white-sand beaches encompassed within the Gasparilla Island State Park.