Chartered Territory

With our guide to bareboating, it's easier than ever to rent and rule your own sailing ship

Feb 13, 2007
Outside Magazine

GETTING SCHOOLED: Go full tilt in the BVI    Photo: Corbis

I HAVE BECOME—I will admit—a sailing dweeb. Since graduating from my Fast Track to Cruising course, I moor coffee tables to couches and call out nautical commands while grocery shopping ("Cookies alee, prepare to jibe!"). I blame the Offshore Sailing School, in party-rific Tortola, British Virgin Islands. As promised, its ten-day Fast Track program transformed me from mountain-town landlubber to bluewater skipper, certified to charter a bareboat—any ship hired without a crew—up to 50 feet anywhere in the world. Let me say that again: Ten days of instruction and charter companies will hand you the keys to a yacht.

The first three days covered the basics. Our enthusiastic 26-year-old instructor went over rigging, points of sail, and elementary seamanship during lectures and outings on OSS's custom-built 26-foot daysailers. The most important and reassuring lesson: It's almost impossible to capsize a larger keelboat, since at least 40 percent of the weight is underwater. Next, along with two other students, I settled into a 49-foot sloop under the tutelage of David Gayton, a salty 54-year-old with a sailing résumé that spans three oceans. While hopping from one island to the next, we practiced the basics—rescues, whipping the huge hull around in tight figure-eights, docking the very expensive boat in very unforgiving concrete slips, and anchoring without damaging fragile reefs. We came to understand the workings of the electric systems and diesel engines and plotted courses that accounted for current and leeway, that inevitable sideways drift.

A thrilling feeling of mastery and humility welled up. On the second-to-last day, we dropped David back at harbor and sailed on alone. We headed downwind five miles to a schooner-turned-bar anchored off an uninhabited island, where I realized that I was hooked—that sailing was in me. I walked over to an attractive woman and introduced myself with perfect ship-to-shore radio protocol: "Sexy Lady, Sexy Lady, Sexy Lady, this is Eric."

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