On the other hand, the interchangeability of boats in a major fleet like The Moorings does give you the opportunity to use a boat like yours in a lot of places. Bennarosh's contract gives him the right to use any Moorings boats for six weeks a year during off-peak times, or two weeks a year each during peak and off-peak times.

"Plus you have three weeks of what they call walk-on privilege," he adds. "If your own boat is not booked, you can sail it for up to three weeks with two weeks' notice."

In total, then, Bennarosh can cruise "for free" nine weeks a year–a nice option if you're retired or have a flexible work life, but not one that all boat owners can use. And if your schedule is not flexible, you may not be able to get the dates you want in your chosen destinations, because the boats may be booked.

Those are realities, but not necessarily disadvantages, Bennarosh says. He says that the main disadvantages in working with a big company like The Moorings is that there is little wiggle room for the owner's wishes, and that so many of the boats are the same, they can be hard to sell later on. His opinions are based not just on his own experience, but on the experiences of countless other Moorings owners and clients who communicate on his website.

"What charter companies do not say is how difficult it is to sell the boats," he says. "I have some boats that have been on the market for two years. It's a nightmare for some people."

For him, the system has worked well, allowing him to trade up to bigger boats over a period of 12 years, without the hassles of hands-on maintenance. But none was necessarily the boat of his dreams, kept in a place where he would, ideally, like to use it.

FULL-TIME OWNER-OPERATOR

Kim KavinCapt. Johan Tordhag

Capt. Johan Tordhag owns a Beneteau 46 sailboat that he offers for charter in his home waters off the coast of Sweden. They're cold waters, which has bothered him for years, not to mention that there really isn't much demand for charter in Scandinavia. He dreamed of sailing in the heart of Europe's chartering community along the south of France and western Italy, the most popular charter destination in the world. His 46-footer was a nice boat, and he assumed clients would love it as much as he does.

He did some asking around, though, and to his disappointment was told a boat like his isn't always a good bet in the western Mediterranean, where charter clients typically request bigger yachts. Tordhag realized he either had to leave his Beneteau in Sweden and take what few charters he could get there, or buy a bigger boat that would stretch his personal resources but let him enter his chosen charter market with better prospects.

In Tordhag's case, the solution was to take a partner and buy the 76-foot CNB sloop INXS, then sail it to Genoa, Italy, where it entered the 2007 summer charter season with six pre-booked weeks of business as part of the fleet at BCR Yachts. Tordhag has a silent partner who takes a piece of the 19,800-euro-per-week about $26,500 charter rate, less the typical 15-percent booking commission paid to BCR. Tordhag himself stays onboard, offering free labor all summer as captain of a three-person crew.

His hope is to make enough money to pay his crew and cover the expenses of his new lifestyle. If his first season goes well, he'll be able to enjoy his chosen lifestyle for many years to come, just like the Stahls and Bennarosh and all of the owners in Hope Swift's New England fleet. He's picked up his first clients in early June in Croatia.

"This is my life savings and my dream come true to have a big boat like this," he said on a sunny, 80-degree day. "And now I'm in a warm spot where you don't have to worry about cold weather."