$$$$, Gasparilla Island (Boca Grande)
Fodor's Review:
Social-register members such as the Vanderbilts and DuPonts still winter at the gracious pale-yellow wooden hotel built by shipping industrialists in the early 1900s. Lodge rooms are not lavishly decorated by today's standards. The cottage rooms are more modern and less spartan, but some are without TVs. The inn takes up much of the town of Boca Grande with its rich-blooded amenities -- sprawling lawns, golf course, and beach club. In summer (mid-Apr.-mid-June), rates are for Modified American Plan or European Plan; October through mid-December no meals are served. Two of its restaurants are off the main campus. Gentlemen are required to wear jacket and tie in the hotel after 6 PM. Pros: historic property, newly painted and upgraded. Cons: forced meal plan is limiting, expensive, hotel rooms are sparse.
Visit the Travel Talk forums for help on planning your trip