Local folklore holds that pirate José Gaspar hid his captives on this pristine island. A gorgeous prison, indeed: The slender barrier island in the Gulf of Mexico west of Fort Myers has pale, powdery sands graced with more than 250 types of seashells.
A single main road runs Captiva's five-mile length, making much of its raw beauty best appreciated by sea kayak. (Buck Key Paddling Trail, a best-kept paddlers' secret, winds past green herons and gators.) There are plenty of finds on foot, too; shoppers here love the intimacy of Captiva Village along Andy Rosse Lane, which houses not only galleries and boutiques, but also a public library, community center, and the historic beachfront Chapel By The Sea. It's a 10-minute stroll from the Village to sweeping Alison Hagerup Beach Park (aka Captiva Beach), a great sunset post for spotting the horizon's famous green flash.
Although Captiva's sunny, mild climate means warm days year-round for its 400 residents, a particularly special time is May to October, when thousands of tiny loggerhead turtles emerge from their nests and make their way slowly to the water's edge. They might be the only islanders who ever feel like leaving.
Where to Stay: Posh and pretty South Seas Island Resort is situated within a 330-acre wildlife preserve spanning two and a half miles of tranquil, sandy beach. Rates start at $149; 800/533-5553 or southseas.com.