The Ultimate Jib Bunny

I'd like to begin at the end. The hind end. Mine, to be specific.

Ordinarily a great expanse of white, my bottom has been transformed into a luminous canvas emblazoned with small, irregularly spaced bruises that stand out like stars in a moonless sky.

As I stand before the bathroom mirror, aghast at the sight of my own buttocks, I can't help but wonder if Heidi Klum's derriere is similarly mottled. It's likely, for we were racing nether cheek to nether cheek, dashing to and fro with abandon, plopping ourselves down upon the accursed rails.

Are her bruises, like mine, intricately patterned? Are her fingers, like mine, so badly blistered she is unable to grasp anything smaller than a Lazy Turtle, the painkilling rum drink that has fueled my headaches these past seven days? I don't know. This is uncharted territory, as sailors like to say. All I am certain of is that nobody told me about sailing's dirty secret: When racing, dress for a hockey game. "When they asked me if I wanted to go sailing, I thought, Cool, yeah, I'm up for anything," recalled Heidi, as we shared a bottle of champagne and compared wounds on the porch of my bungalow at the Bitter End Yacht Club on Virgin Gorda, in the British Virgin Islands. "I didn't think I'd actually have to do anything. I thought I'd just be sitting on a boat, looking, you know, scenic. Not that modeling isn't hard work. I mean, you get up early, the days are long, you travel all the time. But you don't break your toes."

I spared her a catalog of my injuries: After three days of sailing, both my shins were swollen and the color of rotten pears. My left kneecap was scabbed over in two places. My right calf had a contusion the shape of a Rorschach test. Both forearms were bruised from my headfirst dive down a hatch. And my neck bore a distinctive rope burn from a time I forgot to duck during a tack. Here lies Ed. He went sailing and was hung by the neck until dead.

Other than that, I was feeling just fine.

Heidi, a native of the inland German town of Bergisch Gladbach, near Cologne, had never set foot on a sailboat, and I am about as nautical as a bushel of corn. But race director John Glynn assured us that no experience was necessary to participate in Bitter End's 12th annual regatta, in which guests of the resort crewed for some of the world's finest sailors during a three-day round robin of match races. The cast of skippers read like the Who's Who of match racing: Russell Coutts, the New Zealander who skippered Black Magic, the victorious America's Cup yacht in 1995; Paul Cayard, another America's Cup heavyweight who earlier this year won the grueling Whitbread Round-the-World Race; Peter Isler, Dennis Connor's navigator in the victorious 1987 America's Cup campaign, and Isler's wife, J.J., a former Women's World Match Race champion. (The Islers cowrote my bible for the trip: Sailing for Dummies.) The other skippers included Ken Read, John Kostecki, Harold Cudmore and Terry Hutchinson—all renowned sailors. It was like entering a pro-am golf event made up entirely of major championship winners.

The boats we'd be racing were Freedom 30s, single-masted keelboats that were designed to be simple and ponderous. What they lacked in speed, however, they made up for in ability to inflict pain. All hardware was placed knee-high, sharpened-edge out. Cleats were hip-high, and camouflaged. Decks were coated with a nonslip sandpaper that shredded skin like Ginzu knives. Three-inch rails ran the length of the vessel, ingeniously designed to dig into the most vulnerable, baby-soft portions of a sailor's arse as he hiked himself over the side. As one of Cayard's crewmen liked to say during moments of maximum discomfort, "If it doesn't hurt, you're doing it wrong."

By that measure, I was a natural. Everything I did hurt. The first day I was assigned to Coutts's crew—Heidi wasn't due to arrive until late on the afternoon of Day 2—and told to work the traveler. It had a red rope and a green rope and a couple of pulleys that connected it to the sail, and, depending on which way we were pointing, Coutts would tell me to pull on one rope or the other. I could never figure out why. (I later looked up traveler in Sailing for Dummies and learned it had something to do with changing the mainsail's angle of attack. Whatever that means.)

Anyway, there we are, racing upwind in the first heat of the first race, and Courts asks me to pull in his traveler. Cool. I un-cleat the green line and—fwwwishhhh!—it goes tearing through my hands. Uncool. I regrip, pull mightily, the line slips back, I pull some more. The traveler inches back toward its proper location. "Good enough," Courts says, tired of watching me struggle. I cleat off the green rope and become vaguely aware of a voice in my head going: "Owww...." I look at my hands. I have five blisters, three of them bleeding.