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It happens every week of the year in the British Virgin Islands. Clueless boaters from the U.S. mainland—leisure sailors who lack experience and don't entirely know what they're doing—fly down to Tortola, rent enormous catamarans, float them out into the middle of the channel, and for the next seven days proceed to endanger every seaborne object they encounter. This week is no different from any other. Except this week one of those clueless boaters is me.
Truth be told, I'm not a total novice. I've been sailing small boats since I was a child. First it was 8-foot dinghies at a summer day camp on a Massachusetts lake. Later, it was slightly larger Mercuries and Lasers, racing other high-school brats around a three-buoy course in the Charles River basin. (We'd sometimes capsize into the mucousy, radioactive water, then kick to the surface, gasp for air, and narrowly avoid getting brained by a passing Harvard crew shell.) I can tie bowlines, clove hitches, and square knots with the best of them. And the physics of wind and canvas are essentially the same whether you're sailing an 8-foot dinghy or a 36-foot, sleep-aboard catamaran.
As you might guess, though, there are important differences between sailing a dinghy and captaining a bigger boat. For instance, if you happen to run aground in a dinghy, you can roll up your trouser cuffs, step out of your small craft, and nudge it back into the deeper water. Whereas if you run aground in an expensive, borrowed yacht, you can roll up your trouser cuffs, dive into the water, and remain submerged until the insurance claims adjuster believes that you've drowned and thus cannot be held liable.
The stakes are just higher on big boats. They're harder to maneuver in a crowded marina. They have motors, plumbing, and electrical outlets. If you want to pilot them over serious distances, you're required to master a set of complicated skills, including reading navigational charts, communicating via VHF radio, and properly tying a pastel sweater over your shoulders.
I'd always longed to make the leap from dinghies to yachts. Last summer, when my girlfriend, Rebecca, spotted a relatively affordable weekend course held on a river in nearby Virginia, I decided the moment had at last arrived. We enrolled, paid the fee, and spent a few afternoons helming a 29-foot sloop under the guidance of an elderly, part-time instructor. (This man seemed more eager to argue about politics than he was to teach Rebecca and me how to pluck each other from surging swells should one of us ever fall overboard.) Once the hands-on stuff was done, we were administered a written exam—an easy multiple choicer, which we both passed with flying colors. And voilà, we had official certification from the American Sailing Association.
"So does this mean we're ready to charter a yacht and sail around the Caribbean by ourselves?" I asked our instructor, doubtfully.
"Sure, go for it!" he said, looping some frayed rope into a desultory coil on the boat's deck. "A lotta people who do it are less ready than you are!"
Armed with this vote of confidence, Rebecca and I immediately begin scouting locations for our first yachting adventure. Everyone seems to agree that the Virgin Islands are the best choice, since they offer perhaps the most forgiving sailing conditions in the world. The winds are steady (but not overpowering), the islands are close together (so you never lose sight of land), and the rum is plentiful (so if all else fails, you can drink yourself into a sunburned stupor as you await the arrival of the Coast Guard helicopter). We booked a 10-day sailboat rental with a charter company in Tortola and convinced our friends Paul and Rosa—who have zero sailing experience between them—to fly down and join us on the trip.
When we arrive at the marina in Tortola on a Friday afternoon, we're handed a bulging binder full of information about our rented catamaran. "This will be familiar stuff, I'm sure," says the woman at the desk. "Just give it a quick glance. One of us will stop by later to do a checkout sail and make sure you can handle the boat."
We walk out onto the docks, past a flock of wild hens pecking at the tropical grass. Our sailboat is tied to a finger pier and floating in the turquoise water of the bay. Once I'm onboard, I sit down in the boat's cockpit with the binder and begin a furious, sweaty-browed cram session.
Half the subjects in the binder were never discussed in our half-assed instructional course. "Davits"? "Lazy jacks"? I have only a vague idea what these things are. Even more terrifying is the impenetrable diagram of our boat's plumbing system. I am deeply concerned that I will flip the wrong valve and route the toilet's contents into the drinking-water cistern.
Eventually, a barefoot blond guy in wraparound sunglasses ambles over and introduces himself. He's a Brit named Phil, and he'll be conducting our checkout sail. He begins by asking me some probing questions to gauge my knowledge. Having studied up, I acquit myself well. I ask Phil a few carefully phrased questions of my own—trying to strike a delicate balance between 1) finding out things that I actually need to know; and 2) revealing that I am woefully ignorant.
And then it's time to launch the boat and see what we're made of. The first challenge is to motor out of the marina. Phil directs me to reverse us out of the slip, do a 360, and then slalom between the docks and out into the channel.
Catamarans have two propellers, one on each hull. You use them in concert, upping the right prop's throttle if you want to steer left, and vice versa. You have to make constant, sensitive adjustments. Meanwhile, the wind pushes you toward those rocks over there. And the current pulls you uncomfortably close to the gleaming hull of a swanky megayacht—which you would prefer not to punch a hole in with your bow. Overall, the experience is sort of like steering a split-level house across a football field coated with ball bearings.
I somehow manage to get us out of the marina intact. Phil next asks us to raise the mainsail and the jib. We do so, with minor hiccups. After this, everything else goes smoothly. Phil has some dire warnings for us ("The thing about catamarans in high winds," he says, "is that they give you no sign of stress until the mast snaps and swings down on top of you at 40 miles per hour"), but he's mostly satisfied that we won't do anything egregiously stupid.
We drop him back at the marina and then head out into the open water. We're under way, all on our own now. The breeze is powerful, and we start bouncing through the swells toward Norman Island, about three miles away. We're whipping along. The sun is warm and bright. The salt spray feels fresh and cool on our faces. In all the chaos of catching an airplane down here, hailing a minivan taxi to the marina, and then fretting that we might fail our checkout, I'd almost forgotten how much I love to sail.