I’m on a mission to find the stereotypical yacht owner—the snotty yachtie. The crested-blazer and ascot-wearing, cigar-smoking, martini-sipping, zip-code-dropping, sockless gent who these days probably sports a spray-on tan and bleached teeth. The easiest way to differentiate him from his land-based, country club counterpart is his white captain’s hat. He’s mocked in movies and television and featured in every caricaturist’s portfolio.

Since most stereotypes start out as generalizations based on truth, I want to discover if this mythical man of leisure exists in the BVI.

My first stop is the Royal British Virgin Island Yacht Club. Fancy name, I think. Surely here I’ll find a perfectly coiffed and manicured yachtsman bragging about the size of his vessel. I scan the Thursday night crowd but see very few collared shirts and no cigars. Most tables are occupied by families—grandparents, parents, and children sitting together enjoying plates full of sushi. I chat with one such group and discover they are, in fact, a sailing family. After the standard introductory pleasantries and minor interrogation from them (“What brought you to Tortola?” “Do you sail?” “Are you Canadian?”), I eventually do hear them brag but not about their boats. Instead, they share tales of their child’s performance at the last youth regatta. And the only discussion of money is some half-hearted groaning about the cost of a new sail for their kid’s Opti.

Since the RBVIYC was a bust, the next day I decide to try Nanny Cay Marina, but first I take a detour to The Boat House restaurant in Manuel Reef. There, while sitting on the deck overlooking a mangrove island, I meet artist Savanna Redman, who tells me that I’m not going to find the snotty yachtie on Tortola.

“The guys in the rattiest, paint-spattered shirts and tattered Dockers and flip-flops, working on their boats—,” she begins.
“Are the real sailors.” I finish.
“No, are the multi-millionaires,” she corrects me.
“If you ever see the other kind,” her friend Chris adds, “they’re imports.”
“And posers.”

Poser. The insult of insults. In Nabokov’s “A Bad Day,” a young boy, trapped in too-small pants at a party he didn’t want to attend, spends an agonizing day being overlooked and ignored whenever he tries to join in the festivities. At the very end, when a peasant brings in a baby owl, the boy’s previous agony is forgotten. You feel his joy as he looks at this beaked, feathery puffball. Just then, at that moment of elation, he overhears the older cousin he admires tell the girl he likes, “Here comes the poseur.” Instant deflation. Perhaps that’s the difference between the stereotype and the reality—BVI yachties aren’t posers.

The second thing I think of, in response to Savanna’s comment about the ratty clothes, is Stephen Clarke’s book Merde Actually when the British protagonist, Paul West, goes on holiday in the South of France with his French girlfriend and notes how the wealthiest vacationers intentionally ride the rustiest bikes. He mocks the fact that they spare comfort and speed in order to look nothing like the tacky tourists who ride faster, newer mountain bikes on the paths. Maybe BVI yachties are like the French—a sort of shabby chic.

Still not convinced, I decide to ferry over to the Bitter End Yacht Club in Virgin Gorda. While there, I run into Chris Watters, sailing instructor for the RBVIYC, spending his day off in VG. The first thing I notice is Chris’ lid—a trucker’s cap modeled after a naval officer’s chapeau with the word “Commander” in gold felt letters on the front. An ironic captain’s hat. Funny.

While we lunch, Chris blurts out, “They’re rigging it all wrong!” in response to a couple setting up a small craft for their daughter by the dock. “I should go down there and help them,” but just as he’s about to get up, he notes that they’ve fixed their problem. “I don’t know about ascots,” he says. “Maybe in St. Barts. Or stick around for the yacht show. There’ll be some there.” He glances behind us. “If you want to meet a true sailor, you should talk to that guy,” he tilts his head toward a bearded gentleman sitting at a neighboring table.

I walk up and introduce myself to the man who calls himself Captain Vic. I describe what I’m looking for and he laughs. “Maybe twenty years ago, or maybe they wear that stuff on their boats or at functions, but not out here.” When I ask him what “they” do wear on the dock, he points to his own outfit: Mt. Gay t-shirt, shorts, visor, sunglasses, and Sperrys.

“Lace-up shoes?” I ask.
“My flip flops had a blowout last week,” he replies.

We pause in our conversation to enjoy watching Red Sky, a majestic Swan 100 approach the BEYC, then he asks if I sail. I blush and say I’m starting to learn, but admit to my fear of capsizing. “Well, if you ever need a lesson…”