Boca Grande and Outer Islands

Clustered around the old train depot that brought industry to this pint-sized village near the southern tip of Gasparilla Island, this charming community, Boca Grande, has evolved into a playground for the rich and famous – and regular folk as well. Five beaches line the western part of the island, and a grand inn graces the outskirts of "town." Visitors delight in the barefoot elegance, fine outfitters and the miles-long bike paths that traverse the island.

Offshore, North Captiva, Cayo Costa, Cabbage Key and Useppa Island intrigue island hoppers of varied ages, abilities and interests. North Captiva has pristine beaches and a collection of large rental homes and two restaurants; Useppa sports the Collier Inn, a beautiful botanical walk and, proof that good things come in small packages, the tiny-but-terrific Barbara Sumwalt Museum.

Cabbage Key is a stop off in civilization as only islanders envision it: a casual hamburger and seafood joint with a spectacular view surrounded by an inn comprised of cracker cottages. Cayo Costa, mainly a state park, is pristine coastal Florida at its best – wide, unspoiled, white-sand beaches, rustic cabins and tent campsites – and ample bird and wildlife to watch.