Charter a crewed boat, and leave the driving to them.It doesn't matter if your only connection to boating is an old pair of Top-Siders. You can still ship out and experience some of the finest sailing in the world by taking a multiday voyage aboard a rented boat with a hired crew.A crewed nautical vacation - better known as a "term charter" or "crewed charter" - is an exclusive, all-inclusive trip with a well-appointed (if not necessarily roomy) cabin, fine dining and round-the-clock service. Best of all, it acquaints you with all the adventure and romance of sailing the Caribbean. The settings change every night, and the scenery unspools all day, unless you decide to scuttle the itinerary, drop anchor and simply loll. You can take a spin at the helm, hoist sails - or leave all that to your seasoned crew of captain and mate. It's good to be admiral.Check out Elements of Style: our round up of great all-inclusives around the CaribbeanA charter is especially appealing "for groups of friends, or families that want to spend quality time and have an experience that lasts a lifetime," says David Rohr, product manager for The Moorings, which sends out crewed yachts from a half-dozen Caribbean locations. Note that it's not necessary to charter an entire boat to make your getaway; instead, you can book a single stateroom aboard a Moorings or Festiva Sailing Vacations vessel, for example.Since this is the Caribbean, with a sweeping array of distinctive island groups and armadas of sailboats, the cruising options are countless. The waters of the Virgin Islands, the most popular sailing destination, are easy to reach from St. Thomas; boats can even pick you up near the airport. With steady and reliable winds, intimate tropical beaches and sheltered anchorages, those islands offer a classic Caribbean getaway. Closer to home, the Bahamas include hundreds of Gulf Stream islands with incredible snorkeling and miles of deserted beaches. Arcing from Martinique south to Grenada, the Windward Islands offer a mix of sailing conditions and authentic island culture. This is true blue-water sailing, with strong winds and long crossings, but the reward is calling on some of the region's most unaffected islands: Bequia, where locals still hunt whales from rowboats; Carriacou, where donkeys remain the preferred SUV; and the Tobago Cays, a marine national park that provided the idyllic setting for several Pirates of the Caribbean scenes.
While charter companies offer a reliably standardized experience in different locations, for a more personalized vacation you can charter an owner-operated boat. The best way to arrange this is through a yacht broker, who will know the most popular cruising areas firsthand and can alert you to potential drawbacks (anchorages in the Grenadines, for instance, can have a swell that causes a boat to roll at night). Brokers such as Julie Nicholson of Nicholson Yacht Charters, a 60-year-old firm with a client list that includes Ted Koppel and Liam Neeson, have in-depth knowledge of hundreds of vessels.One of your first considerations when planning a chartered cruise should be the size and shape of the boat. Vessels range from sloops that only accommodate two passengers ("two-packs") to yachts with several staterooms. Mono-hull boats offer old-school romance and a traditional sailing experience, says Nicholson, while twin-hulled catamarans boast better stability, a more spacious deck area and less draft, which allows them to get closer to beaches and reefs.A good rule of thumb: The smaller the passenger capacity, the more likely the owners will be the ones crewing the boat. It will also reflect their interests and personalities through details such as stateroom décor, toiletries, the on-board library and even cutlery and stemware. A broker is really a yachting yenta who will have a good handle on the personality - and tastes - of each boat and crew."This is a people business," explains Charles Swaim, owner-operator of the sloop Phaedrus, a 50-foot two-pack based in the U.S. Virgin Islands. "It's really not about the boat; it's about the people on the boat. It's not a hotel business. It's much more of a matchmaking business."When consulting with a broker, make your expectations clear: High energy or laid-back? Formal or casual? Two dives a day or lots of beach-hopping? Gourmet meals or a pub-crawl of every rum-slinging beach shack in the Lesser Antilles?"We ask them if they're purists, if they want to feel the wind fill the sails," says Nicholson. "Do they want a Captains Courageous personality or do they want someone philosophical who can talk about Kierkegaard? Do they want the crew to keep their distance and wear uniforms, or do they want to sit in the cockpit and have the captain explain the stars and teach them navigation? We ask them, 'What makes your heart leap?'"Potential customers should also communicate what makes their spirits sink, whether those be personal-space issues or connectivity concerns. Life on a boat is an up-close-and-personal B&B, without Wi-Fi or broadband service.All in all, though, Nicholson con-siders a term-charter vacation a singular experience. "A cruise is entirely tailor-made," she says. "At a hotel, what you see is what you get: the same beach, the same neighbors. On a boat, it's changing all the time, and it's therapeutic and cleansing to go out on a boat and see a wave curling in front of you." 
SET SAIL Let one of these expert sailing outfits steer the course:The Moorings One-stop shop for multiple Caribbean destinations. 888-952-8420; mooringssignature.comFestiva Sailing Vacations Offers multiple destinations.866-575-3951; festivasailingvacations.comNicholson Yacht Charters Offers owner-operated charters to multiple destinations.800-662-6066 ; nicholson-charters.com Phaedrus Owner-operated sloop in the USVI. 340-690-6740; yachtphaedrus.comOnline Editor's Note: Before your charter, check out our latest Snorkel and Reef Report for information on the Top 10 reefs and dive sites you may come across on your trip.
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