For fully crewed charters, choosing the crew is more important than selecting the boat, Hamilton says: You'll be spending a week or more in a confined space, so it's important to ensure that personalities won't clash. Capable brokers know the crews on the yachts they charter and will make sure there's a good fit—provided clients are clear about their preferences and habits. "Some people don't tell us what they really want," says Hamilton, "and then they get upset when the trip is not what they expected." If good food is a priority, see to it that the crew includes a serious chef. Are you bringing children? Some crews are more child-friendly than others. If you want to learn about sailing, be sure to get a captain who is eager to share his or her knowledge.

The size of the boat is another important consideration: Make certain your charter suits the size of your group. It's never a good idea to sail away with people you hardly know just to fill a berth and reduce expenses. In terms of bareboating, you can save a lot of money by booking an older vessel, but if something breaks, you might get stuck with the problem unless you're dealing with a reputable company that will make the repair quickly or give you another boat. Again, your best bet is to use a broker.

Most yachts are available for a minimum of five to seven days. Some offer discounts for longer cruises, and prices vary depending on the season and location, but beware of steep discounts. Brokers dramatically drop their rates during the slow season, but that isn't necessarily the most enjoyable time to sail. In general, the ideal months for boating in the Caribbean are November through April; in the Mediterranean, May through September; and in New England, June through August.

For all its appeal, a yachting vacation is not for everyone. Smaller boats are much more vulnerable to adverse weather than cruise ships, so an unexpected storm can easily alter even the most carefully planned itineraries. And the diversions aboard yachts can't hold a candle to those provided by their mammoth counterparts. Nonetheless, tens of thousands of charterers find the experience deeply satisfying. "Our fourteen-day charter sailboat adventure was nothing short of spectacular—brilliant blue sky, warm aqua seas, and temperatures you only read about," says Adam Benson, of Bedford, Nova Scotia, who sailed through the British Virgin Islands with his partner and two other couples. "The experience of moving our hotel—the boat—from place to place each day was new for us and truly made us feel like we had ten minivacations wrapped into one big one."

Big Ships vs. Yacht Charters
Which options float your boat?

Big Ships

• Visiting several different countries or islands for short excursions.
• Organized activities around the clock.
• Traveling with hundreds or thousands of others.
• Swimming in a pool.
• Ordering from a menu in a dining room where you share a table.
• Sleeping in an air-conditioned cabin.
• Going on structured shore excursions with dozens of shipmates.
• Drinking in shipboard bars and cocktail lounges.
• Sailing on a fixed itinerary.