We all know what happens when six champion one-design keelboat teams meet in the British Virgin Islands to race for glory in 43-foot bareboats of dubious equality. It’s a whole lotta fun, frustration and challenges by the day, but it’s one heck of a sailing adventure that comes with an equal-size rum buzz. For my teammates from the J/35 Falcon, winners of the 2024 Helly Hansen Sailing World Regatta Series in Detroit, and present in our signature straw hats, that’s how this Caribbean Championship plays out.
Our BVI adventure begins at the Sunsail base in Road Town, Tortola, where the first order of business is to source a whisker pole for the boat’s furling jib. Fellow team member Jim Allen and I set out to recon nearby boatyards, where a friendly charter captain merely wishes us luck in securing one. So, it’s Plan B: With a trip to a local lumber yard, we score 14 feet of two-by-four. Our crewmate Freddie Blackmer drills for four hours, and rigs the lines and blocks he’s packed with him.
With our whisker pole approved by the regatta’s “technical committee,” the bareboat’s bottom cleaned by local divers, and the vessel properly provisioned, we’re as ready as we can be. Over on the mothership catamaran, which is packed with friends and family, the Straw Hat Crew is eager for whatever comes our way.
The first race of the weeklong island-hopping regatta is our first chance to see how we measure up against the competition. The long first leg is an upwind beat, which is a learning curve, to say the least. Our baggy Dacron sails certainly aren’t what we’re used to trimming, but we work them hard, playing the vang and halyard tension in the puffs, and easing everything in the lulls.
The charter captain we’d met during our pole search had tipped us off to which way to go on this leg, and he was spot-on, but Annapolis’ Team Mirage—two-time defending champs led by Cedric Lewis and his partner Fred Salvesen—is right on our tail when we score our first race win at the finish inside Tortola’s Trellis Bay. We celebrate with a few adult beverages and dancing by the fire on the beach, comfortable with the knowledge that we had a competitive boat.
After spelunking the boulders of The Baths the next morning, it’s a bareboat battle to Leverick Bay, in Virgin Gorda Sound. We’re late for the broad-reach start, tangled with Team Casting Couch, from Annapolis, but we battle like heck searching for puffs over the next few hours and score a third. It’s a keeper, but Team Mirage finishes ahead of us.
Our plan for this night is to win the Mount Gay Rum drink-recipe contest with a BVI version of the Hummer (a nod to Bayview YC’s legendary bartender Jerome Adams). But ice cream is nowhere to be found, and our provisioning expedition returns with half-and-half, vanilla extract and ice cubes. The results are terrible. Expedition No. 2 returns with a bizarre rum-raisin, lactose-free, fat-free healthy alternative, and in the end, the judges agree that rum and ice cream is a winning combination.
Having overserved Hummer test batches, we have a crack-of-0800 race start to the island of Anegada the next morning. And what do you know? We’re cozy with the Casting Couchies again, but after a long and fast race, we break free and score another win. Mirage is fourth. Time to bar-hop and chow down some fresh lobster.
Scrub Island is our next destination—a long upwind slog across the Caribbean Sea and a second-place finish. Team Mirage is back in fourth place again, and we start thinking that maybe, just maybe, we can pull off an upset. It’s not looking good for the champs.
Popping into the Scrub Island Resort for the night is a welcome change from life on the mooring ball. Real showers, shore power, and tank refills get the Straw Hat race boat and mothership crews back to civility. And here I finally have a chance to chat with our PRO Dick Neville, who maybe senses that we’re taking this whole thing too seriously.
“It’s supposed to be fun,” he says. To treat it otherwise is the wrong idea. “It’s not the North Americans.”
I smile politely. But I’m not buying all of what he’s selling. We race to win, right? And why is he telling me this? Do I look stressed? We’re having a ball, but honestly, we are here for the double: We want the title and the party. But I know what he’s getting at, and his words linger in my head as I wander back to the poolside bar to hang out with the crew.
Scrub Island to Sandy Cay is the next challenge, and the angle is a beam-ish reach. We haven’t yet used our two-by-four pole contraption, and while we nail the start and jump into a big lead, deploying the cumbersome piece of lumber takes a good 10 minutes.
Team Omaha, led by BVI regular Stephen Hosch, is roaring up from behind while we fumble with our pole. We deny them several attempts to sail over the top of us, but in fighting the battle, we lose the war, leaving Team Mirage to run free to capture its first win.
Our lead is now down to 3 points, with one leg to go. A third for the final race is all we need, but at Foxy’s bar on Jost Van Dyke, Neville lets us in on a secret: He intends to run windward/leeward races on the final day. That changes the math, but we’re up for the challenge.
And lo and behold, we’re cozied up with the Casting Couchies on the starting line again, and this time we get ourselves into trouble. We’re last across the line, with our bow pointed to a faraway finish at Norman Island. Third is the best we can do, but Team Mirage pockets another win. We’re now down to a single-point lead before one final two-lap windward/leeward exercise. The windward leg is only 0.7 miles. This one has to be won in the start.
We set up for the favored pin, which is the giant race-committee power catamaran, dive low to kill time, but as we wind up to start, I’ve got too many wraps on the winch and cannot wind it in quick enough. Team Omaha rolls us, and all we can do is bail out and hope for a shift or better pressure.
We Hail Mary to the right, and when we tack, Omaha and Mirage cross our bow, in that order. The Mirage crew demonstrates its champion crew work, superb driving, and award-winning adjustable whisker pole to overtake Team Omaha and complete the most amazing comeback ever in the history of this Caribbean Championship.
Upon reflection of the outcome, I realize that Neville, like the Oracle in The Matrix, had given me the winning advice, but perhaps I did not heed it well enough. The Straw Hat Crew had plenty of fun, but maybe, just maybe, we should’ve dialed down our focus on winning the darn thing. It’s the BVI. Relax and enjoy. That is the point.
