Now I Know Why Rich People Buy Boats

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Not everything has been perfect on this sailing adventure. For instance:

  • The sun down here is evil. It’s like a merciless eye of heat that is forever staring at your forehead. The tips of my ears and the tops of my feet are badly broiled. The reflection of the sun off the sea has fried the undersides of my arms. And my face has assumed a vaguely Naugahyde-ish texture. I think this week may have added nine or 10 years to my apparent age.
  • Being aboard a boat all the time, you miss out on what’s happening ashore. We’ve hiked around the islands some, toured a tiny rum distillery, and even attended a reggae festival. (Every song mined the complex relationship between religion, social justice, and truly stankalicious kind bud.) But we could have made a more concerted effort to get in touch with the local culture of the islands—instead of allowing ourselves to remain cosseted in the wealthy, lily-white boating culture of the harbors.
  • Along the same lines, it can be easy to nurture a hatred for fellow boaters. In crowded harbors, where the boats are moored close together, there’s a bit of a tenement feel—in that you can hear other people’s conversations and you’re exposed (often literally) to their dirty laundry. While most of our floating neighbors have seemed cool and low-key, some have been loud, obnoxious chumps. Popped collars. Prominent luxury-brand logos. Crap-eating frat-boy grins. As you may be aware, the very act of yachting has some unfortunate class connotations, and I was occasionally queasy about the company we were keeping.

On the plus side, we found many things to love about our maiden voyage as bareboat charterers. (This sounds sort of dirty, but it means we rented a boat without a captain or crew and sailed it ourselves.) Among the delights:

  • There’s a real sense of camaraderie that develops when you share a boat with other people. We scoffed early in the week when we saw a family that had printed up customized, matching T-shirts with the name of their boat on the front and individualized job titles on the back (“Captain,” “First Mate,” “Deckhand”). But now we kind of wish we had shirts like that. There’s something to be said about a vacation that forces you to cooperate with your pals and solve a series of problems. We’ve turned into a tight-knit team this week and grown proud of our various roles: hauling in the sails, reading the navigational charts, mixing the fruity drinks. In seriousness, nothing cements a friendship like shared accomplishment.
  • I have never slept better in my life. When you’re hoisting sails, cranking winches, and hauling the dinghy up on a beach, the physical exertion throughout the day can really start to accumulate. There’s also the constant battering from the elements, as the sun bakes down and the salt spray grinds into your skin and hair. By the time it gets dark—and you’ve drunk three nightcap piña coladas—you’re pretty tired. The gentle rocking of the swells in the harbor tends to lull me into dreams moments after I collapse into bed.
  • The lifestyle in general, for all its absurdity, is pretty fantastic. You wake up and immediately hop into the warm, turquoise ocean a few feet from your bedroom. You spend all day floating through gorgeous scenery as the wind blows through your hair. After enduring the initial sunburns and muscle aches, you grow tan and fit. It turns out there’s a reason that rich people like to buy boats. It’s so they can eventually fake their own deaths, evade their creditors, and escape to seedy international ports. But it’s also because boats are really fun.

Our final day, returning to Tortola, we put out full sails and really let it rip. On a beam reach—perpendicular to the wind—we rocket along at 12 miles per hour. This may not sound fast (and it does put a damper on my pride when I remember that a person pedaling a bicycle could comfortably keep up with us and not break a sweat). But you’ll have to believe me that on a sailboat it feels like warp speed. You feel the weight of the wind straining at the sails. You hear the hulls slicing through the waves.

The truth is, this is what I came for. The weather is nice, the snorkeling is lovely, the beach bars are mellow. But what I’ve remembered this week is how wonderful it is to sail on a windy day. The sailboat is an ancient, simple, perfect invention, and to be at the helm of one—harnessing the gusts and leaping across the sea—is to tap into something profound and elemental.

We return to Road Harbor, Tortola, and funnel ourselves between the red and green buoys that mark the entrance. We drop our sails and motor into the marina, and then ably (if anxiously) maneuver our cat into its slip. Once we’re safely tied up to the dock, I let out the little pocket of breath I’d been holding in the bottom of my lungs since I first took control of this boat a little more than a week ago.

Nothing went wrong. No one fell overboard. We didn’t run aground or snap the mast or turtle over in a storm. We didn’t ram our bow through the hull of another boat. We never got lost or misread the charts. No one got whacked in the temple by a boom swinging across the deck at hellacious velocity.

“How’d it go?” asks Phil, the guy who’d tested us on our initial checkout sail and deemed us capable.

“Not a single problem,” I say, almost but not quite in disbelief.

“Did you enjoy yourself?” asks Phil.

Did I enjoy myself? I have to say, I honestly contemplated—as we were making the final turn into this harbor—just stealing the boat and sailing it to Venezuela. I didn’t want this to end.

And now I’m back in my cramped apartment in Washington, D.C., where my view is not of ocean but of pavement and brick. I gaze at the nautical chart of the Virgin Islands that I’ve taped to the wall. And all I can think is: When can we do that again? And where can I print myself a T-shirt that says “Captain”?