Click here to view a slide show on sailing.
On the first leg of our trip, we sail from Tortola across the wide, windy expanse of the Sir Francis Drake Channel. It takes an hour or so to reach Norman Island—a small, green bundle of hills poking out of the Caribbean. We drop our sails, motor into a bay ringed by high cliffs, and secure our catamaran for the night.
Dusk is falling, and it's hard to see, but on the other side of the harbor we make out what appears to be a bobbing pirate ship. A pirate ship that's blasting Duran Duran. Curious to learn more about these New Wave pirates, we lower our inflatable dinghy into the water, yank the starter cord on the outboard motor, and buzz across the bay for a closer inspection.
Upon our arrival at the ship—it's a floating bar named the Willy T, moored a few hundred yards from shore—we find a dozen other dinghies already tied alongside. The soused sailing crowd is sucking down bottles of Red Stripe and munching on baskets of conch fritters. We cleat off our dinghy and climb aboard to join the fun. As I step up onto the deck, I immediately collide with a drunken woman in a disheveled bikini. She's attempting a sort of glassy-eyed stumble-dance to the driving beat of "Hungry Like the Wolf."
If there's one thing I'm learning about boating culture, it's that alcohol and sailing go together like marijuana and bowling. Which is to say: exquisitely. (Save for those occasions when your bowling ball jumps into the neighboring lane. Or you capsize and your whole family drowns.)
When we were reviewing our boat's equipment checklist back at the marina, the woman from the charter outfit specifically mentioned only two items. Not the lifejackets. Not the flares. The two things she wanted to be 100 percent sure that we had onboard were the corkscrew and the bottle opener. And perhaps now is also a good moment to note that the name of our boat is Rummy Cat.
The British Royal Navy, for most of its history, maintained an official alcohol ration. Those serving on her majesty's ships were ladled out up to a pint of 95-proof rum per day. This delightful custom began in the 17th century and lasted all the way up until 1970. Had it endured just a bit longer, we might have found out what happens when a shnockered British sailor gets placed in charge of Trident-class, submarine-launched nuclear missiles.
The brutal conditions, mortal danger, and foul casks of fresh water that plagued the 17th-century British seafarer seem like they might well have conspired to drive a man to drink. But why are modern leisure sailors so intent on getting themselves sozzled? In part, it's that we're on vacation (and damned if we're not gonna get good and wasted on vacation). In part, it's that we figure we're not driving a car, so it must be safe to drink (never mind that when something goes awry on a boat, the consequences can be ghastly). Mostly, though, people on boats drink to excess for the same reasons people everywhere else drink to excess. Either 1) they are experiencing an uncomfortable proximity to family members or 2) they are striving to have sex with a stranger.
The Willy T perfectly encapsulates this duality. Preppy families zoom up in their dinghies, with a passel of kids all bundled into teensy lifejackets. They sit at one of the picnic tables arrayed on the ship's deck and order cheeseburgers and fries. Dad quickly downs four to six cans of beer.
Meanwhile, steps away, a man swaying on his feet looks poised to lap a shot of tequila out of a giggling woman's clavicle hollow. And above the bar, a digital photo frame plays a disquieting slide show—a series of snapshots all taken aboard the Willy T during its crazier nights. There's a topless woman with whip-cream-dolloped nipples. Then two middle-aged ladies bending over in bikinis, flashing rear-view camel-toe. It ramps up from there.
After a few beers and a basket of fritters, the four of us return to our dinghy and seat ourselves on its rubber pontoons. Darkness has fallen. We click on our headlamps, fire up the outboard motor, and chop back across the harbor beneath the dome of a huge black sky. Aiming our headlamp beams at the patch of inky sea that's dead ahead of us, we stay on the lookout for lobster-pot buoys that might snare in our propeller.
When I wake the next morning, the sky outside the bedroom porthole is a cloudless royal blue, and the air is hot. I clamber out on deck, strap a snorkel mask on, and hop off the back of the boat to cool myself in the ocean. I quickly spot a sea turtle the size of a manhole cover gliding 15 feet below me. He pauses to nibble at a coral reef and then flaps away.
In the afternoon, we motor out into the channel—where the gusts sweep between the islands—then hoist our sails and start tacking upwind. We're falling into a nice rhythm, learning the feel of the boat. I spin the wheel and swing the bow around. Rebecca cranks a winch to tighten the mainsail until it snaps full of wind with a satisfying crack.
After an hour or so of perfect sailing weather, we notice an ominous gray sky looming on the horizon. "Maybe we should find a harbor before that storm hits us?" suggests Rebecca.
"Oh, we'll be fine," I say, with the assurance of a man who has very little idea what he is doing. "It doesn't look too bad. Might miss us."
Minutes later, our boat is enveloped by a shrieking tropical squall. Thumb-thick raindrops sting our cheeks and burn our eyes. I can't see more than 20 feet in front of me, where the sideways sheets of water overlap and become opaque. My foremost fear is that I might lose my bearings and scrape up on some rocks.
Once we've found our way into a protected cove, we exhale, collapse into the cockpit, and watch the subsiding storm from beneath our canvas bimini top. Soon enough, a little motorboat steers into the harbor and bounces toward us over the swells. We see its name—Deliverance—on its transom as it pulls up alongside us.
Turns out it's a mobile bodega. It sells supplies to boaters (and hauls away their garbage) for a reasonable fee. "Would you like to buy anything?" shouts the woman at its helm, peering out at us from beneath the large brim of her black rain hat.
Having made it through the storm, I believe our crew has earned itself a tot of rum. We ask her for a bottle, which she quickly produces. And how very comforting it is to know that even as we float in a near-empty bay, in a driving rainstorm, our next stiff drink is never far away.