Gasparilla Island (Boca Grande)

Before roads to the Lower Gulf Coast were even talked about, wealthy Northerners came by train to spend the winter at the Gasparilla Inn, built in 1912 in Boca Grande on Gasparilla Island, named, legend has it, for a Spanish pirate who set up headquarters in these waters. Although condominiums and modern sprawl creep up on the rest of Gasparilla, much of the town of Boca Grande looks like another era. The mood is set by the Old Florida homes and tree-framed roadways. The island's calm is disrupted in the spring when anglers descend with a vengeance on Boca Grande Pass, considered among the best tarpon-fishing spots in the world.