With some 1,350 miles of shoreline, it's not surprising that Florida is a boating and sailing mecca. In fact, you won't be anyplace near the water very long before you see flyers and other advertisements for rental boats and sailboat cruises.
The Moorings (tel. 888/952-8420 or 727/530-5651; www.moorings.com), the worldwide sailboat charter company, has its headquarters in Clearwater and its Florida yacht base nearby in St. Petersburg. From St. Pete, experienced sailors can take bareboats as far as the Keys and the Dry Tortugas, out in the Gulf of Mexico.
Key West keeps gaining prominence as a world sailing capital. Yachting magazine sponsors the largest winter regatta in America here each January, and smaller events take place regularly.
Even if you've never hauled on a halyard, you can learn the art of sailing at Steve and Doris Colgate's Offshore Sailing School (www.offshore-sailing.com), headquartered at the South Seas Plantation Resort & Yacht Harbour on Captiva Island, with an outpost in St. Petersburg. The prestigious Annapolis Sailing (http://annapolissailing.com) has bases in St. Petersburg and on Marathon in the Keys.
Florida Boating & Fishing, available for free from the Florida Sports Foundation (see the introduction to this section), is a treasure trove of tips on safe boating; state regulations; locations of marinas, hotels, and resorts; marine products and services; and more.