Matt Gross for The New York Times The S.V. Illusion, on which the Frugal Traveler sailed as a crew member, anchored in Saline Bay off Mayreau Island in the Grenadines. Slide Show »

This weekend’s cover story, “Sailing the Caribbean, the Frugal Way,” has been a long time coming—three years, to be exact. Back in September 2006 I visited Jost Van Dyke, a tiny isle in the British Virgin Islands, for another Frugal Traveler story, and it was there, while staying on White Bay, that I met a Florida family of four who’d rented a sailboat and invited myself and a friend aboard against gin and tonics. Impressed by both their generosity and their freedom—with the boat, they could go wherever they liked, whenever they wanted!—I began to experience to figure out how I, a non-sailor destitute of sailboat-rental funds, could live their luxurious lifestyle.

Over the months and years, I picked up bits and pieces of information from friends, books, Web sites and even my barber, Miles. I learned that boats all over the world were taking on “working passengers” for ludicrously low rates, that experience was not necessarily necessary and that sailing, contrary to what I’d always assumed, was not solely for the ultrarich. In early October, 35 months after I left Jost Van Dyke, I flew into St. Lucia to rendezvous with the S.V. Illusion and begin a new adventure.

Read my full story here.

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