Let the Wind Be Your Guide: The Top Charter Sailing Vacations

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If you want to get away from it all—even from the confines of a land-based resort—a bareboat charter cruise is the ideal vacation. Hire a skipper for a few days if your cruising skills are rusty, or experiment with flotilla sailing, in which a group of boats follow a leader who handles the navigation chores. Fun can be had in any boat of 25 feet or larger, but we recommend a yacht in the 34- to 44-foot range. At this size, you can get private cabins for two or three couples—a modicum of privacy that will keep you all on speaking terms until the end of an extended cruise

The Virgin Islands: Sailor's Cruising Mecca
Anyone pining for a Caribbean the way it ought to be need only float a boat among the baubles of the Virgin Islands. From mooring to mooring—the islands are only miles, or in some cases, yards apart—the five-star resorts, haute cuisine restaurants, and beautiful bays make each docking an adventure. Sailors will find the funky along with the fancy. Sir Francis Drake never had it this easy, and you won't have the Spanish Armada to contend with either.

The Virgin Islands, cleaved by history but joined by the sea, stretch from the U.S. Virgin Islands' St. Thomas in the west to Anegada of the British Virgin Islands in the east. The islands between—St. John, Tortola, Virgin Gorda—and a few dozen more, are filled with comely coves, perfect for snorkeling and splashing. Sailors can navigate by sight (okay, charts help), since the islands lie close enough to see several at a time. All in all, it's only about 35 miles as the crow flies, but that crow misses out on all the twists and turns and coves and channels. Sail all day in at an easy pace, or stabilize your sea legs at the long beaches of Virgin Gorda, or even the duty-free shopping malls on St. Thomas. Don't forget to put in at the famous Foxy’s on Jost Van Dyke, where you can pin your business card to the ceiling of the open-air, beachside bar and kick back with a cocktail. And don't dare the irascible Foxy Callwood to pull out his guitar and make up an embarrassing calypso song about you on the spot—because he will.

Practically Speaking:
Your options when chartering a yacht range from day charters to long-term charters, either with crew or bareboat (you crew yourself), and with a group or by yourself. As well, you can opt for power yachts over sailing vessels.

Crewed yachts come with a professional sailor, and have the options of meals, fishing and sporting equipment, perhaps a bar, and other choices. Costs vary with options, with the season, and with the number of passengers on board. They can be expensive, from $2,000 per week, without provisions. Others offer all-inclusive packages, from about $1,000 per person per week. Bareboat charters start at about $900-$1,500 per week (off-season, two-eight people) for the boat, and require the renters to have sufficient sailing and anchoring experience to handle the boat. In the winter, bareboat charters can range $2,000-$6,000 for two to as many as ten passengers. One option: charter a bareboat and work as crew, but hire on a skipper who knows the ins and outs of the local waters.


Karl Luntta is the author of Moon Publications' Jamaica Handbook, Caribbean Vacations, Virgin Islands Handbook, and Caribbean Handbook , as well as several other guidebooks to Caribbean destinations, plus Short Nature Walks on Cape Cod, Nantucket, and the Vineyard. Karl has contributed articles and photos, even fiction, to national magazines, websites, and newspapers. He is a columnist with the Cape Cod Times.

Published: 30 Nov 1999 | Last Updated: 8 Nov 2010
Details mentioned in this article were accurate at the time of publication

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