"I never thought it could be so rewarding," says Hank Gordon of Point Pleasant Beach, New Jersey, who, together with his wife, Jacqui, and their two children, ages four and seven, chartered a skippered 38-foot catamaran with another family in the British Virgin Islands in April. "Our other vacations tended to revolve around getting together for the next meal. But being part of the sailing experience as a family—hoisting the sails, snorkeling, windsurfing, swimming, diving, fishing, kayaking, and hiking—made eating meals almost secondary."

Where to Cast Off
The British Virgin Islands and the Bahamas are ideal choices for first-time charterers, because their islands are close together, providing calm waters and short hops between destinations. The entire Caribbean is prime charter territory in the winter months, while the Mediterranean and the Aegean are favored spots during the summer. Emerging hot spots include Croatia, Greece, Turkey, Grenada, and the Canary Islands. Vietnam and Thailand are also developing into popular destinations for U.S. passengers. "These areas appeal because they're beautiful, affordable, and still untouched," says Sunsail's Karen Morris.

Charter Options
Charter companies offer an array of choices to suit experienced mariners as well as those who've never set foot on a boat. Fully crewed yachts leave passengers with nothing to do but enjoy the ride, while skippered boats and bareboats require more of everyone on board.

Another consideration is whether to go for power or sail. Powerboats can cover greater distances in less time, but they are noisier and cost more to rent and operate. Sailboats, though slower, can be more relaxing. "Powerboats are best for people who want to get to a destination quickly," says Ed Hamilton of Ed Hamilton & Co. Yacht Charter Agents. "On a sailboat, getting there is part of the fun."

Both powerboats and sailboats range in size from about 30 feet to well over 200, and cost from $2,000 a week to more than $300,000. Kim Kavin, editor and owner of Charterwave.com, a Web site covering the industry, says the per-person cost of chartering most yachts up to 80 feet can be as much as the price of a balcony cabin on a cruise ship when you include all the big-ship extras. However, charter yachts are typically all-inclusive, sparing travelers the unpleasant surprise of countless additional charges. "Anyone who has ever taken a cruise will tell you that they couldn't believe their credit card bill when they got home," Kavin says (see "The Perrin Report").

Finding the Right Fit
With the fleet of charter boats growing at a clip, it can be difficult to sort through all of the available options without professional guidance. Kavin recommends using a yacht charter broker, as opposed to dealing with the ship's owner directly, but stresses the importance of finding a broker who is both reputable and easy to work with. Charter brokers make their money from fees paid to them by the yacht owners, so some are more interested in closing deals than in ensuring the right match between client and yacht. If you can't find a referral from someone you trust, Kavin suggests using a broker who is affiliated with one of the four main professional organizations: MYBA, CYBA, FYBA, or AYCA. A good broker or charter company will also assist with purchasing trip insurance, flights, and pre- and post-charter hotel rooms.