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.

The post The Ultimate Charterboat Championship appeared first on Sailing World.

Cedric Lewis, his J/105 co-skipper Fredrik Salvesen, and their band of blue-shirted merrymakers from Annapolis, Maryland, arrived early to the Helly Hansen Sailing World Regatta Series Caribbean Championship in the BVI with a master plan. As holders of the title from a year earlier, they had more than enough time to plot their defense, and plot they did. They locked in their ace crew, chartered a mothership catamaran to cargo their provisions, people and potable water, and then set up their Sunsail 41 to be as slippery as possible. Over five days of racing, they were ­virtually untouchable.

With Hurricane Tammy churning menacingly close to the Leeward Islands, most competitors arrived mere hours before regional airports and ferries closed. Some crews never made it off the continental US. While it looked as if the fleet would be grounded in base for a few days, Tammy gracefully departed, and the first of five distance races got underway on a tropical Sunday afternoon off Cooper Island. For the week’s first challenge, dubbed the Islands Race because it encircles Cooper, Ginger and Salt islands, the hurricane flipped the traditional easterly trades, so the fleet was sent counterclockwise around Salt and Cooper in a light northwesterly.

In the expected chaos of six teams, five of them new to the 41-foot charter boats, the start was a frantic affair with a few boats on or near the line, but a few others were caught off guard while trying to figure out how to work the mechanics of their cruising cockpits. From the melee, Team Mirage promptly broke away and led comfortably around the western corner of Salt before turning upwind and into the heaving hurricane swells. Nearly two hours and many tacks later, Team Mirage put its first win on the scoreboard.

Hot on their transom was the talented squad from Holland, Michigan, led by Tom and Mary Bryant, winners of the Helly Hansen Sailing World Regatta Series in St. Petersburg, Florida, with their S27.9 Matros. Due to an unexpected twist of inventory at Sunsail’s Tortola base, Team Matros found itself on a 46-footer, much more substantial than the 41s allocated across the fleet. While benefiting from the extra waterline length, Team Matros’ longer steed was, however, laden with a generator, air conditioning and other accessories that would theoretically even things out over the course of the week. And while there was some quiet consternation from others in the fleet, it was the opinion of regatta PRO Dick Neville—with decades of experience running the charter-boat fleet races at the popular BVI Spring Regatta—that the Matros syndicate could enjoy their AC, but all would even out across a variety of ­conditions over the week.

Third across the Cooper Island finish line were the California Space Cadets of the VX One that earned its Caribbean Championship berth at the San Diego regatta. Skipper Charlie Welsh arrived in the BVI on a hot streak, having won US Sailing’s Mallory Cup. This young six-pack of friends and teammates were new to charter bareboat racing, but it didn’t take them long to figure out the nuances of their laden vessel.

Finishing mere feet behind the Cadets were the New Englanders of Carolyn Corbet’s Team Elektra, IOD sailors who won the Marblehead edition of the Regatta Series. In the moments before the Islands Race, they unfurled their jib for the first time and quickly realized that it was massively oversize and near impossible to trim correctly. To either tack the boat or sheet the sail home properly, Corbet reported, they had to partially furl it. But as engineers and young critical thinkers, the Elektrans got to work after the race to solve the challenge—rum undoubtedly fueling the innovation.

Next to finish was Team Exile, a late entry to the regatta when Jeff Davis’ Chicago-winning J/111 team surrendered its berth. Team Exile, led by Andy Graff on the big wheel, was short two crewmembers who were unable to reach the regatta because of hurricane travel snafus. Graff, an accomplished doublehanded racer on his J/88 with teammate Scott Eisenhardt, was nonplussed, other than what to do with all the extra provisions. They each had their partners to assist with the trimming, so all was good on board.

Last across the Cooper Island finish line was the young and enthusiastic crew of Bruce Irvin’s Team Shamrock, which put in maximum effort despite being handicapped with a mainsail that was a good few feet short of full hoist. Suffice to say, they drew the slow boat, but Irvin’s fun-loving crew quickly accepted their fate; the revelry to come would more than make up for the unlucky boat draw.

The mainsail on Shamrock’s boat, clearly pilfered from something much smaller, could not be replaced overnight, so for the following day’s leg from the Baths to Bitter End Yacht Club in Virgin Gorda Sound, Neville spotted them a one-minute jump on the fleet. But even that wasn’t enough as, one by one, teams cruised past. Team Mirage was, again, first to Bitter End, making quick work of the course that took the fleet through the Dog Islands and into Virgin Gorda. The Space Cadets scored a second, finishing ahead of Team Matros by a few lengths. Team Elektra grabbed fourth, Exile was fifth, and Shamrock rocked in a few minutes later.

With a Bitter End Yacht Club lay day to relax and jump into the official Wave Beer Can Series, the racers convened the next morning at the watersports center. After a short briefing, they hit the sound in the colorful cats for some spirited buoy racing. The two divisions of Hobie Waves and Getaways raced together, and the Cadets, through all means possible, took advantage of the no-rules racing scheme and won both classes. They followed up with a ­narrow ­victory later that evening at the Mount Gay Rum Cocktail Contest with a tasty ­concoction called “Astro Punch.”

The following morning, the fleet set off to a new destination on the traditional championship route: Scrub Island Resort & Spa and Marina Cay. Team Shamrock got its jump-start and was first to short-tack its way out of the channel while the rest of the fleet lay chase, bouncing each other from side to side until out in the open ocean and into some loose reaching. Team Mirage found itself looking at a fleet of transoms as it exited the sound, but it later pounced at Scrub Island when the front-runners attempted to cut the corner.

“The wind shadows on this course were significant, and those guys were moving along before they hit the wall,” Lewis says. “We steered clear of the shoreline, and to be honest, we got lucky.”

Such fortune in the final mile netted them a horizon job into the Scrub Island finish. Team Elektra, meanwhile, having engineered a better jib lead with borrowed blocks and spare dock lines, had remarkably better pace and handling. The crew put a second place to their score line, proving all along that it had been the boat, not the sailors, holding them back. The Cadets were third, Matros fourth, Exile fifth, and Shamrock was in familiar territory.

The Scrub Island pitstop was a ­welcome respite. While some teams napped, swam or snorkeled, other teams scrambled ashore to the resort for a complimentary rum punch, a pool swim, and a luxury lunch in the air-conditioned dining room.

With many more miles to go to reach Jost Van Dyke before sundown, the race committee hailed all teams back to their boats for the start of the day’s second leg. Irvin’s pleas to the race committee to allow his team to start with the fleet was granted, and the Shamrock squad promptly engaged with Mirage in a pre-start duel that found both of them OCS. Despite the outcome, it was a highlight of the regatta for Irvin. The two were once rivals from back in their junior sailing days, and Irvin was thrilled to be able to square up against his one-time rival. Team Matros, however, got a clean getaway and quickly established a lead it would never relinquish as boats slowly made their way to a finish line set off the picturesque anchorage of Sandy Cay. Here too the Elektrans notched another second-place finish to inch ever closer to Team Mirage in the standings. Mirage was third to the island, the Space Cadets fourth, Shamrock fifth (its best finish yet), and Exile cruised in across the finish not far behind.

The Soggy Dollar Beach Bar and later Foxy’s Bar and Restaurant served as natural post-race gatherings, which carried on into the early hours.

The championship’s notorious Leg Five, which includes a clockwise loop around Sandy Cay and its surrounding reefs before leading the fleet through Great Thatch Cut at the Western end of Tortola, started off with a slow and clean start. But the morning’s promising wind went light just as the boats tried to navigate past Sandy Cay’s reefs. Crews held their breath as they held impossibly thin lanes, creeping past the submerged rocks. Heaving swells pushed boats ever closer, eventually creating a frantic scene of calls for water and engines in reverse. When it was all eventually sorted, Mirage was first to reach Great Thatch Cut and the finish of the shortened course, notching another win before proceeding under power to Norman Island for the ­afternoon’s buoy races.

With a weather mark tethered to a ­mooring deep inside The Bight, Neville pondered the sanity of a half-mile weather leg in such a small anchorage but proceeded with the plan for two windward-­leeward contests. Mirage nailed the first race and then the second, even with a second-­row start. Lewis, Fredrik and Missy Salvesen, Greg Larcher, Vernon Sheen, Lilla Salvesen, Vince Yannelli, Kaila Lewis, and Molly Hughes Wilmer had once again conquered the BVI and the championship (with the help of their mothership skippers Tina Lewis and Debbie Larcher). While their defense plans are not yet in motion, Lewis says, they will come to fruition after some much-needed recovery.

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