Bareboat Racing in the BVI

Do not think that bareboat racing is any less competitive than any other kind of sailboat racing

Do not think that bareboat racing is any less competitive than any other kind of sailboat racing

The burbling of the percolator in the galley accelerates frantically as the bubbling crude’s strength began to build. Soon the crew’s clinking mugs fill the galley sink as the baitfish leap over the line that tethers Sohcahtoa, our Sunsail Jeanneau 41, to the rocky shore of Peter Island in the British Virgin Islands.

We all know that the real wake-up call is next. After a brief discussion of the dive mask anti-fogging merits of dish soap versus saliva, it’s all hands over the side with Scotchbrite pads to have a look at the bottom. We’ve seen worse, which makes the excited racket coming out of snorkels a bit of a mystery. I speak tourist snorkel, having mastered common phrases like “Spotted ray!” or “Anchor’s set!” But I haven’t made it to the Duolingo module containing, “Shoal draft keel! How the heck are we supposed to go to windward with that?!”

With the bottom scrubbed, we enjoy freshwater showers of a length that would be the envy of cruisers everywhere, because we’ve come to race, and full water tanks are slow.

The thought of the 46th BVI Spring Regatta & Sailing Festival has pulled our New England crew through another winter, where shoveling snow and scraping windshields are just more training for coarse and fine-tune sail trimming. Now it’s the end of March and 86 boats with crews from 17 countries have come to soak up some sunshine, and no doubt some rum, in this sailor’s paradise.

Numerous classes are packed with high-tech racing machines, but we’re racing in the bareboat fleet, in a jib-and-main class with a very narrow handicap range in these identical or well-matched charter boats. We eye the rivals in our 8-boat class. I don’t think the Italian crew, who are also racing a Sunsail 41, did much snow shoveling over the winter, but they look fit and ready to go. The British-flagged Bavaria 36 in our class has crew from three different countries; they come together at this regatta every year to enjoy each other at maximum speed. Skill levels in these bareboat fleets range from Olympians and national class champions to round-the-cans racers; the same kind of mix as in the higher-tech racing classes.

We make short work of stowing the bimini, the dodger and the sail cover, removing any unnecessary windage that could slow us down. Bareboats are meant to be raced as chartered. There’s no need and no room for bringing go-fast gear to change sheet block ratios or other rigging elements. The 8 to 10-knot breeze swirling in the anchorage is unusually light for the BVI, where the reliable easterly trade winds have given way to an odd southwesterly flow.

The warmup race for the sailing festival part of the week, typically a circumnavigation of Tortola, has been wisely shortened by the race committee to a triangle around several of the islands on the south side of the Sir Frances Drake Channel. The downwind finish is a patience tester, as we rotate the crew through holding the 106 percent jib out wing-and-wing. Charlie’s and Doug’s long arms are the most useful. We’re first across the line, but we owe time to a few competitors in the bareboat fleet. We’ll check the results when they’re posted. In the meanwhile, we crack open some ice-cold Heinekens, because full beer cans are slow. We later discover that on corrected time, we won by 6 seconds.

That afternoon we make a quick trip back to the Sunsail base for water and ice, then celebrate with a rum drink after snorkeling. We soon discover that while we’re on fire off the wind, the bag of charcoal briquettes from the local supermarket isn’t. There’s no lighter fluid and no outboard with a gas supply (because dragging a dinghy is slow). However, the crew is engineer-heavy, so we’ve soon built a teepee of rum-soaked paper towels, matches and wooden clothespins. The rosemary chicken and roasted corn on the cob is sublime.

The first leg of next day’s Scrub Island Invitational is a simple reach in a northerly that results in epic fleet compression in the lee of the southernmost bluff on Beef Island. We’ve opted to ghost through the dead zone and begin to suspect that the shouting to starboard may be what’s powering the converged fleets on the longer rounding arc. The Gordian knot loosens as competitors beat to the finish. We take on our daily ice and water at Marina Cay, where a dolphin and her calf circle us as we wait for the launch to the prize-giving party. We enjoy a rum punch and get a chance to thank some of the many volunteers who’ve taken vacations of their own to make sure the racing goes smoothly.

The layday begins with not checking e-mail, followed by no client meetings at all. The closest thing to a pressing deadline is getting into the water at Hallovers Bay on the west side of Coopers Island while the morning sun perfectly illuminates a school of more than 50 blue tangs. Doug spots some cuttlefish, and Alec swims with a turtle and a ray on the way back to the boat. It can’t be all grinding winches, after all. We’re not just here to sharpen our sail trimming and tactics for the coming keelboat season in our home port of Marblehead, Massachusetts, where a long, wet winter hasn’t even considered loosening its grip as March is giving way to April. The regatta is also a great opportunity to keep the communication and teamwork strong in the off-season.

We wrap up Day 1 of the BVISR proper with a pair of bullets, but the Brits are too close for comfort, and the Italians are fast enough off the line that we can’t maneuver past them until the first reaching leg. We are faster downwind than any of the other Sunsail 41s—all that bottom-scrubbing, perhaps—but we need to keep an eye out for the lighter and well-sailed Bavaria.

In the relatively light air next morning, the first race goes to the Brits as we settle for second. Next up is a downwind start that has the fleet compressed in the flaky breeze. As we begin to pass the Italians, they press their leeward position, taking us up to a close reach before the overlap is broken, at which point we insist on a return to proper course. They’re so focused on the battle that the war’s in danger as the mark recedes to windward. After some bilingual shouting, they finally head off, rounding ahead of us onto a close-hauled port-tack drag race to the second mark.

We can’t get enough elevation to sail over them, and even a brief starboard tack in this light stuff would allow the Brits to pass. The top spot on the podium hangs in the balance as Alec foots just enough to build speed, and it takes every bit of the leg up to the tip of Flanagan Island to sail under the Italians, come back up, and make the turn toward the finish line in a controlling position for the final beat. There’s enough tacking that the Brits are able to finish so closely behind us that we’re concerned about the few minutes we owe their Bavaria on corrected time.

After heading for the harbor, we’re shocked to learn that the Italians have protested us. In the protest room at Nanny Cay Marina, they present alternative facts that claim the overlap was never broken. As the guy trimming the main from behind the skipper, I’m kicking myself for not having the GoPro on deck. The RC is in the unenviable position of two irreconcilable narratives, and they opt to disqualify us as windward boat, putting the Italians and the entire fleet ahead for that race. We’re reminded of Paul Elvstrøm’s timeless quote, “You haven’t won the race, if in winning the race you have lost the respect of your competitors.”

We are fired up for the final day of the regatta, where the persistent light breeze may mean only one race. Not only do we need a bullet, we also need a boat between us and the Italians to salvage second, which is exactly how the day and the regatta come to an end. We take an early and decisive lead, and the Bavaria Brits also finish well ahead of the Italians.

The sunshine and music at the Nanny Cay awards ceremony bring home the festival aspect of the event. We make our way over to the Bavaria crew to congratulate them on a very well sailed regatta. They’re a happy international mash up of Brits, Irish and Americans, and were most gracious in their assessment of the week. We pop both crews’ champagne prizes to share as we hang on the beach and swap sailing stories. They’d sailed well, and resisted messing with anything but the sail trim to gain the top of the podium, where they’d stood with the full respect of their competitors. 


There are some great opportunities for racers—or cruisers who want a challenge—to enter a charter class in the well-run Caribbean regattas. Our crew alternates between the BVISR, which can field 40 bareboats in a typical year, and St Maarten’s Heineken regatta, which can have twice the entries. Both regattas are being held in 2018, but with a limited number of bareboats following Hurricane Irma’s decimation of the charter fleets, so get in early.

There are three regattas that traditionally have strong bareboat classes

The Heineken Regatta is in its 38th year and runs over the first week of March in St. Maarten. The racing is full-on, as are the legendary festivities shoreside.

The BVI Spring Regatta (BVISR) is held at the end of March. The islands have a well-deserved reputation for hospitality and great sailing conditions, and 46 years of experience makes for a smooth and fun-packed week.

Antigua Sailing Week, which started in 1968, is in late April. That’s tough for we New Englanders who are busy prepping our boats for the season, but may be a perfect choice for racers from Texas and the south, whose boats are already in and itching for that first perfect start.

Team Merlin chartered with Sunsail ( for the 2017 BVISR

Tim Sheehy keeps his Bristol 35.5, Dragonfly, in Marblehead, Massachusetts

January 2018


2.4mR's racing at the 2018 Clagett Regatta-US Para Sailing Championships credit Clagett Regatta-Andes Visual

Host for 2021 U.S. Para Sailing Championships Announced

The 2021 U.S. Para Sailing Championships will be hosted by The Clagett Regatta at Sail Newport, in Newport, R.I. on August, 24-29, 2021, according to a joint announcement from the host and US Sailing. "We have had a very long working relationship with US Sailing and look forward more


Cruising: Reflections of an Old Salt

I am 90 years old, dwindling in mind and body and fear living too long. Twenty years have passed since I last weighed anchor. Still, when a Carolina blue sky is polka-dotted with billowing cumulus clouds and the wind blows fair, I sorely miss raising sail and setting forth. I more


Waterlines: Solo Sailing Again, Naturally

In spite of the fact I came to the sport of sailing alone and untutored, in a boat I acquired on my own, I never really aspired to become a solo sailor. It just sort of happened. All these years later, I still never explicitly plan to sail anywhere alone. I’m always happy to more


Racing The M32 Class

This year the M32 celebrates its 10th birthday. Swedish Olympic bronze medalist Göran Marström and Kåre Ljung designed the M32 in 2011 as the latest addition to an already impressive portfolio that includes the Tornado, M5 A-Class, M20 catamaran and the Extreme 40. Two years more


Know how: Cleats, Clutches and Jammers

Since the invention of rope, there has also been a need to belay or secure it. Every sailboat has rope on board so, unless you own a superyacht with captive reels or winches, you’re going to have to find a way to make it fast. (As a side note—and before you reach for your more


Antigua Sailing Week Announces Women’s Mentorship Program

In partnership with the Antigua and Barbuda Marine Association, Antigua Sailing Week is launching a mentorship program to encourage women and girls to join the sport of sailing. President of Antigua Sailing Week, Alison Sly-Adams says, “When we devised the program, we looked at more


Experience: A Badly Snagged Prop in Haiti

When a winter norther blows through the Bahamas, the northeast trades can reach gale force as they funnel through the Windward Passage between Cuba and Haiti. After waiting for a lull, though, we had a fabulous beam reach aboard our Liberty 458, Distant Drummer, from Santiago de more


Charter Cruise to La Paz Mexico

Just 24 hours before our scheduled charter in the Bahamas, the government clamped down again on visitors from the United States. Having endured two Covid-19 brain swabs in preparation, I looked at my packed bag on the floor and reached for the rum. I could, at least, pretend I more