CONSIDERING that none of us newbies had any idea what we were doing, the voyage south from St. Lucia was going well. At 10:30 a.m., amid gray but not ominous skies, the S.V. Illusion  the 75-foot, two-masted schooner on which I and two others were novice sailors  had weighed anchor off the coast of Vieux Fort, a sleepy city at the island’s southern tip, and steered into deeper waters. The sea was mild, with five-foot swells rocking us just enough to make walking a conscious effort, and when Norman Garnett, the Illusion’s 61-year-old English captain, gave the order, we scrambled to pull, feed, winch and cleat a series of ropes that unfurled our three sails, which caught and tightened in the wind. We were sailing!  At first, we cruised along without a care. The sun revealed itself, we applied SPF 30 and we fetched paperback novels to read on deck. A pod of pilot whales surfaced off the port bow, then vanished, heading west. This was, it seemed, a cinch, a few minutes of complicated labor in exchange for untold hours of relaxation. But midway, we began to notice something odd. We were tilting to starboard. Severely. The thickening swells, in fact, were almost touching the worn wooden rail that arced around the ship. Was this normal? The wind was picking up, droplets of rain coming down. Was this safe?  “All right, kids!” shouted Norman, popping up providentially from below. “We’re going to bring the staysail in!”  Frantically, we reversed the morning’s procedures. As the squall whipped us, we loosed one coil from the staysail winch and fed out the line as Norman pulled in the other end, and soon the staysail was safely away. The Illusion righted herself, and we glided on toward St. Vincent and the Grenadines, our next port of call, both shaken and invigorated by the danger and the drama, the chaos and the education, the teamwork and the hard-won, elemental pleasure of harnessing the wind.  “That’s what I’m paying for!” Steve Hill, a 45-year-old from north London, announced that evening, once we’d moored in Wallilabou Bay, a tiny inlet on the volcanic island of St. Vincent.  We were not, however, paying much. Our berths aboard the Illusion cost us each $55 a day, a sum that covered breakfast, dinner, basic instruction in sailing, plus mooring and customs fees  pretty much everything except lunch, beer and off-shore excursions. And beyond those tangibles, we were getting access to the world of yachties, those fortunate souls who drift on the wind from port to port, stopping for snorkeling, drinks and tale telling at sparsely inhabited tropical islands where ferries and prop planes rarely land. I’d always craved that sense of freedom, but with sailing classes in New York City generally starting near $500 and yacht charters in the thousands of dollars, this Frugal Traveler despaired of ever attaining it.  Then I discovered Crewfinders.com. And GlobalCrewNetwork.com. And FindaCrew.com. And FloatPlan.com, CrewFile.com, WorkOnABoat.com, WorkOnAYacht.com and any number of similar Web sites that link up sailors (both amateurs and professionals) with boat owners and captains. The jobs range from basic deckhand duties to skilled work, like engineers and cooks, and span the globe, from the Caribbean and the Mediterranean to Southeast Asia and the South Pacific.  With no experience, however, I had to look past the paid gigs to the unpaid ones. Many of these posts seemed to be written by late-middle-aged guys seeking female companionship (fair enough: solo sailing is lonely), but I also found a Bahamas-bound couple with teenagers seeking someone to help cook and clean. Not for me, perhaps, but for the right person, it’s a free tropical holiday.  At several of these sites, I saw ads for the S.V. Illusion and followed links to the boat’s Web site. Built in Rio de Janeiro in 1976, the Illusion had spent years as a treasure boat, ferrying divers in search of sunken colonial-era wrecks (it helped discover the Atocha, a $450 million haul of gold and silver), before Norman, a native of Liverpool, England, bought it in 2003. Since then, he’d been plying the waters between Trinidad and St. Martin, taking on up to eight crew members for as little as two weeks or as long as three months, and for just enough money to break even. No experience necessary: this was the ship for me.  I e-mailed Norman suggesting tentative dates for a 16-day sail in early October; he wrote back asking for a $100 deposit via Western Union. I complied, but to be sure this wasn’t a scam, I contacted Misty Tosh, a TV producer from California who’d blogged about her stay on the Illusion. Don’t worry, she told me by phone, you’ll learn to sail, maybe swim with sea turtles and have a crazy time.  Good crazy or bad crazy?  Three weeks later, I was deep into good crazy, courtesy primarily of Norman, the captain. With his Popeye-like forearms, grin that glinted gold and freckled skin that concealed deeper layers of pale white and bright pink  like a sunburned snow leopard  he looked the part of a weather-beaten sailor with hundreds of thousands of sea miles under his belt. But this was only his latest incarnation, he told me, having previously been a bodybuilder, a lawyer, the chairman of a television production company, a mercenary in Africa and a manufacturer of amphetamines (for which he said he served time in prison).  Uniting these multiple identities was his caustic Liverpudlian sense of humor. His delightfully twisted outlook allowed only extremes. Everything was either the best (“Oh, they have the best steaks in the Caribbean  the best!” he growled about one island) or the worst, the ugliest, the most bloody awful. His temper was sharp (he’s the captain, so his word was law) but you couldn’t take his rebukes personally. Once, a rope I was pulling in got trapped and stuck, and Norman yanked it from my hands, yelling at me for failing to pay attention. I could’ve sulked, but 10 minutes later he was grinning again, and so was I.
Having no boat to call his own, the Frugal Traveler shells out $55 a day to join the crew of a schooner for a two-week immersion in the sailing world.