Race to Kick Back, or Kick Back and Race

A diehard cruiser takes to tropical waters for a regatta and likes this new twist on the bareboat theme. A feature from our August 2010 issue

October 6, 2010

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Bareboats stripped of their biminis and dodgers are kitted out for competition as they spar in Sir Francis Drake Channel off Tortola, in the British Virgin Islands. Todd Vansickle

I was guilty as charged. A red Mount Gay cap, an impressive tan, half a dozen T-shirts, and a passport stamped by a Caribbean customs official were only part of the damning evidence.

Yet they were proof positive that my mission-to race as many boats and meet as many crewmembers as possible during the annual British Virgin Islands Spring Regatta & Sailing Festival-was a resounding success.
Proudly, at times mischievously so, I hopped from boat to boat; at innumerable shoreside cocktail parties, my behavior earned a more pejorative name. I loved every varied bit of it, wrangling rides aboard a local’s Hughes 38, a snowbird cruiser’s Swan 57, and a Catalina 42 Mark II chartered by a group of British doctors who race a 5.5 Meter in Cowes in the summer.

This whole adventure got going in earnest during the winter of 2009, when the British Virgin Island Tourism Board thought the best way to gain exposure for its little corner of paradise would be to invite foreign journalists to come down and sample the festival and ensuing regatta firsthand. And that’s just what I did. That March, I hopped on a plane and left slushy New England far, far behind, and started my escape on a bareboat at the Sailing Festival. For this series of warm-up races intended to help crews work out the kinks, our steed, courtesy of the Tourism Board, was a chartered Jeanneau 362 that was part of the Sunsail Sailing Vacation bareboat fleet.


It’s the board’s belief-and I’m now a believer-that the treasures of the 60-island territory are best explored via a bareboat charter devoted either to racing or cruising, your pick. And to further convince us of that fact, the board pulled out all the stops and supplied us with food, drink, and landside accommodations-with the boat, of course, as the central attraction.

Well, after spending a week afloat in the Caribbean under sunny skies and steady trades and running off to hike a trail and get a massage on lay day (see “Spring Regatta Info,” see below), I’m more than convinced that this was a no-brainer indoctrination. The entire week, from the festival through the regatta, was nothing less than a blast, the crews of each boat endowed with equal measures of the spirit of fun competition and joie de vivre.

What I came away with, besides the T-shirts and the tan, was the certainty that the crews of the bareboats fought and played as hard as the crews aboard their own boats. Heck, even I started getting into the gymnastics of racing teamwork, and I’m a diehard cruiser. Go figure.


While this brand of vacation-full-on fun, competition, and phases of intense activity intermingled with loads of self-indulgent relaxation and partying-was new to me, it’s well-known to regatta organizers and participants, who are as committed as the tourism officials to finding new ways to make the event and the destination appeal to snowbound sailors in northern climes.

“We want to get the word out that it’s fun, competitive, and easy to do,” says Bob Phillips, speaking in his dual role of regatta chairman and head of the race committee. “You can reserve a boat, fly down, spend a day or two preparing and practicing, and race in competitive classes against competitive sailors.”

A bit of perspective is appropriate: Over the course of its 39-year history, the B.V.I. regatta, along with the festival, has evolved to attract a combined fleet easily exceeding 120 boats, and sometimes hovering near 130, with the bareboats contributing heartily to that total. Notable is that even in recession-burdened 2009, the event drew 122 boats, 33 of them bareboats; constituting the largest class, they were split into two divisions.


Organizers hope one day to hit a peak of 150 boats, which Tortola’s Nanny Cay Marina, site of the regatta village, can accommodate. To that end, according to regatta director Judy Petz, regatta organizers in 2010 debuted a new charter class called the International Yacht Club Challenge as a way to encourage yacht-club members worldwide to participate in the racing. Three teams, one representing the Royal B.V.I. Yacht Club, one from Puerto Rico, and one from Boston, took the challenge; each raced aboard a new Sunsail Jeanneau 42i.
Adds Phillips: “This is a great way to get growth in the class and bring in a group that otherwise wouldn’t consider sailing on bareboats. You get to come down and have a great time. What’s there not to like? The B.V.I. is just a special place to come sailing.”

Crew Dynamics
To those who still find it odd that someone would suggest hightailing it to the Caribbean and racing a boat other than his or her own, Phillips and others have the unassailable comeback.

“The bareboat class is as competitive as all the others,” says Phillips, who runs Doyle Sailmakers B.V.I. Limited when he’s not racing or serving as an international race officer. “We have more Olympic medalists sailing in the bareboat classes than in the racing classes.”


Aside from the rock stars, the regular charterers fly in from Europe and North America ready to race, Phillips adds. “They come early, and they prepare. They can’t change the gear on the boat, so they’re limited. If the boat comes with seven forks, there better be seven forks at the end. If it came on the inventory sheet, it has to be on board. We have access to all the sheets, so we know the boats.”

Charterers will dive on the hulls to make sure there are no barnacles, tune the rig to ensure it’s right, and basically “make the adjustments they’re allowed to make,” says Phillips.

“They can take biminis off, but frames must stay aboard and can’t go below. Sail covers can be rolled down to the top of the boom or taken off completely. Anchors have to be removed from the bow. In general, the anchor and chain get moved to the base of the mast. We want anchor and chain to stay in the anchor locker, but it isn’t always possible. Serious crews put the chain and anchor at the base of the mast. Some teams will check the sails thoroughly and make sure the charter company has reasonable sails on the boat.”

That’s the nitty-gritty. Take a step back and hear this vote of confidence from Josie Tucci, brand manager for Sunsail Sailing Vacations, one of the companies that offers race packages for the event.

“It creates a match-race effect,” Tucci says. “You’re racing like-for-like boats, so it all comes down to skipper and crew.”

From the P.O.V. of Participants
Consider the circumstances of these two bareboat crewmembers, on teams that took top spots in the 2009 regatta.

First is Gustavo Pinto, from Puerto Rico. Despite his background as a sailing instructor and racer of F18 Hobie Tigers, he and the crew he wound up with-fellow members of the Latin American press-were largely strangers to one another, and they were further handicapped by language barriers: Each sailor spoke a different Spanish dialect.

Aboard a 36-footer supplied by Sunsail (Gustavo, like me, is a journalist, and his trip was also sponsored by the territory’s tourism board), the skipper ran into more complications.

“Coming from multihulls, it’s kind of difficult to race monohulls,” he said. “And with the language problem, we had to make an effort to understand each other. I teach kids sailing, and in this boat, I did the same thing: I explained to everyone what and how I wanted everything to happen. ‘This is our goal and that’s it,’ I said. It came together well for us.” To say the least: Team Puerto Rico II aboard a Jeanneau Sun Odyssey 36i placed fifth in Bareboat Division B and won the Tourist Board prize for the best Tourist Board Team.

For David Downie of Britain, who won Bareboat Division B aboard a Beneteau Cyclades 43, the experience offers up a bit of everything. “Our crew is a pretty mixed bag of age and experience, and I find chartering a bareboat enables us to enjoy the thrill and excitement of regatta racing without being concerned about crew ability and handling a racing boat,” he says. (For more from Pinto and Downie, see “Winning Ways,” below.)
Perhaps the regatta’s Petz best expresses the feelings about the bareboat class.

“When you start cranking at seven or eight knots, you get just as excited as if you’re on a tricked-out raceboat,” she said. “It’s a wonderful way to have a vacation plus step it up a notch. And after the race, you get to tell the tales. You still have the thrill. When you pick up the wind and you’re sailing fast with your crew, it’s ‘Woohoo!’ I think that’s where a bareboat has a wonderful advantage for those people who can’t ship boats in and campaign.”

Winning Ways
Before you even think about taking your place on the starting line, hear this concerning charter boats:

Bob Phillips, 2009 Regatta chairman: “Read your sailing instructions! They’re clear in the notice of race in Caribbean regattas, where bareboats are prevalent.

“We’ve had people who sent spare halyards up on messengers,” Phillips says. “It’s not, perhaps, a violation of written instructions, but it’s certainly a violation of the spirit, and we frown on that. Some of the smaller charter companies have special suits of sails they hold for owners of the charter boats to use in the regatta. It’s just flat not fair. People think they can get away with this stuff, but there are no secrets in this industry.”

Gustavo Pinto, sailing instructor and journalist: “If you know the basics, you can do it. It’s good to have the skipper with his eyes always on the boat, and someone he can trust to look ahead off the bow to the other boats. I watched only the boat and the sails, and the guys who were racing with me watched the field, the lay lines, and other boats,” Pinto says. “I concentrated on getting boat speed. If you try to do both, you’ll lose time.”

Pinto’s advice: Find crew you can trust and with whom you can communicate. You need strong sailors to trim the sails as much as you need crew with enough weight for the high side. And you need people who are committed. “When it’s time to stop drinking and get ready for the next day, you need team players.”

David Downie, Bareboat Division B winner: “Racing on a chartered bareboat is never going to be as exciting as campaigning one’s own boat, but that, however, is expensive and time-consuming.”

Downie advises you charter from a reputable company, make sure the bottom’s clean, and do the best you can with your sails. Try to get your main as flat as possible. Get good halyard tension on your genoa. Experiment with block positions on the genoa. Bareboats aren’t raceboats, so concentrate on speed to windward rather than trying to point as high as possible. And work on getting a good start. It’s very important, particularly on short regatta courses.

Spring Regatta Info
The 2011 B.V.I. Spring Regatta & Sailing Festival, running from March 28 to April 3, marks the event’s 40th anniversary. For details, log on to the website (; the site also includes details about chartering.

For information about visiting the British Virgin Islands, consult the B.V.I. Tourism Board website (

For details about trails, consult the B.V.I. National Parks Trust website (
For more details, including water-sport rentals, visit the Bitter End Yacht Club website (, the Leverick Bay Resort & Marina website (, and the Nanny Cay Resort, Marina, & Boatyard website (

Elaine Lembo, CW’s deputy editor, had a blast chartering, cruising, and racing in the B.V.I.


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