Baring It

“You must never forget that you are in the Caribbean while your friends and family are freezing their behinds off back home, and you therefore owe it to them to enjoy all aspects of the Caribbean lifestyle”
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Most sailors charter a boat in the British Virgin Islands for a relaxing, sun-kissed Caribbean sailing vacation. I’m thinking that splashing about at 0630, scrubbing slime off a boat’s bottom with a Scotchbrite pad while trying not to get reacquainted with the previous night’s rum drinks, would be considered neither relaxing nor a vacation by most people. And yet here we are, a bunch of otherwise normal middle-aged guys from New England, swiping away at the bottom of a charter boat in a bay on Peter Island. Welcome to the wonderful world of bareboat racing, or condo racing as it’s becoming affectionately known. 

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 The crew looks pensive

The crew looks pensive

Basically, instead of (or as well as) chartering a boat for a week’s lazing around the islands, you charter it for a week of racing in a Caribbean regatta. During the day you race it—as hard as you can, or want to—and après-sail, well, you kick back and snorkel, enjoy a few cold ones, or hit one of the numerous parties for which these regattas are renowned. Doesn’t sound too bad, does it? Most hardcore racers turn up their noses at the thought of racing a production family cruising boat, which is what most charter boats are. But unless you’re talented enough to be paid to sail on one of the real raceboats, or lucky enough to have friends with boats invite you down to crew for them, this is the only way most of us will get to enjoy taking part in a famous Caribbean regatta. 

It’s a Tuesday morning at the tail end of March, and the BVI Spring Regatta and Sailing Festival is about to get under way. The five of us bobbing about in the warm waters of Great Harbor—Charlie, Scott, Alec, Tom and me— usually race on Charlie’s J/105, Merlin, in Marblehead, Massachusetts. Our ride for this regatta is Kief, a Sunsail 41, aka a Jeanneau Sun Odyssey 409 decked out as a comfortable vacation platform complete with air conditioning, an all-encompassing bimini, full water and fuel tanks, main and genoa sheets led aft to a pair of winches at the helm, and—thanks to Charlie’s thoughtful shopping—many cases of beer.

 The competition, Dundee, flies to the weather

The competition, Dundee, flies to the weather

How are we going to turn this sheep into a wolf? Easy—strike the canvas and stow it belowdecks, take the anchor off the roller, shower profusely to use up the water, and drink the beer. The boat will therefore become lighter by the day, ideally reaching peak performance mode by Friday, the first day of the regatta. Hopefully the same will be true of the crew, though given the amount of beer we have to get through, this is doubtful. 

We also re-lead the jib sheets to the halyard winches on the cabintop while Charlie and Scott tune the bejesus out of the rig to get the sag out of the forestay. The sails look a little tired, so we dispatch Tom—the only one of us with what might be called a “winning smile”—to sweet-talk the sailmakers at the Sunsail rig shop. To our surprise and delight, his plaintive descriptions of frayed stitching leading inevitably to expensive damage bear fruit in the form of a crispy new main and jib.

 Kief is reefed down for the last-day cold front

Kief is reefed down for the last-day cold front

Since Charlie, Scott and I have some experience in Caribbean bareboat racing, we know that getting to know your boat is essential if you’re going to have any hope of doing well. This is where the Sailing Festival part of the regatta comes in. We have two races, one around Tortola and another across Sir Francis Drake Passage to Norman Island, to use as warm-ups, plus a lay-day to work on weight reduction. It will also give us a chance to get the measure of the competition, which is always tough. We settle into the usual groove—Charlie driving, Alec and Scott trimming, Tom and me lending a hand when needed and offering gratuitous advice/insults from the rail when not.

Our 12-boat class, Bareboat B, includes two other Sunsail 41s plus a handful of Sunsail 44s—Jeanneau 44i’s, which I know from experience are quick boats—along with some bigger Beneteaus. Even though they have to give us time, beating them will be a tall order. 

 Local music enhances the Caribbean parties

Local music enhances the Caribbean parties

The opening event, a counter-clockwise race around Tortola, starts in picture-postcard conditions and by going inshore around the top of the island, out of the current, we slip past not only most of the bareboats, but a good many of the cruising class boats. At the end of the five-hour race we correct out to second place, just 19 seconds behind the Sunsail 44 Dundee, crewed by a gnarly-looking bunch of Dutchmen. The takeaways are: sailing wing-and-wing the length of Tortola is very hard work; you cannot stop trying to keep the boat going fast; our main competition, in addition to Dundee, is The Whalers, a group of veteran sailors from New Bedford, Massachusetts, on Tatjana, another Sunsail 41. The next day, when we squeak past Dundee to win the second “fun” race, the Caribbean Insurers Island Invitational, the grudge match is well and truly on. 

But these regattas are not just about the racing; you must never forget that you are in the Caribbean while your friends and family are freezing their behinds off back home, and that you therefore owe it to them to enjoy all aspects of the Caribbean lifestyle—rum drinks, assorted beautiful anchorages, regatta parties, snorkeling, generally having a laugh—without holding back. With this in mind, we continue working very hard to lighten the boat’s liquid load, visit the renowned full moon party at Trellis Bay, and make sure to drop by Nanny Cay for a spot of partying. It is here I meet some of the Dundee crew, who turn out to be very pleasant gentlemen of a certain age—“the youngest of us is 65,” one informs me proudly. 

 The apres-race parties are an integral part of any Caribbean regatta

The apres-race parties are an integral part of any Caribbean regatta

This intel leads us to hatch a nefarious plan—to camp on them after the starts, force them into tacking duels, and see how quickly these AARP-eligible Hollanders tire of scrambling to and fro across the cabintop. (Unfortunately this is a two-edged sword, as my own creaking joints testify after the first day’s racing.) On Friday, the regatta’s opening day, we quickly find that once they break free from our cover Dundee points higher and sails faster, but we are as fast reaching and downwind. As long as we don’t let them get away we have an excellent chance of beating them on corrected time. 

In boxing, a good big guy will beat a good little guy every time, but in sailing, handicaps let little guys punch above their weight. The Jeanneau 409 is fast and nimble, and the Dutch find it hard to put enough water between us to beat us on time. We go into the last day a single point ahead, with two bullets and two seconds to Dundee’s two bullets, a second and a third place. As for the New Bedford crew on Tatjana, they’re sitting in a comfortable third, having themselves beaten Dundee the previous day. 

 The crew shirts struck fear into the hearts of the competition

The crew shirts struck fear into the hearts of the competition

On the final day a cold front muscles its way over the islands, bringing 35-knot squalls and stinging horizontal rain. But some excellent helming from Charlie keeps us ahead of Dundee for most of the first race, and when they do slip past we hang on for another bullet. The final race is a repeat, minus the squall, and The Whalers on Tatjana also slip ahead of Dundee for a Massachusetts one-two. 

That night’s prize giving is a soggy affair, but we don’t care. The rain is warm, we’ve finally won a bareboat regatta, and under the Boston Yacht Club colors we’ve also won the International Yacht Club Challenge, with its prize of a Sunsail charter. That will be auctioned off for charity, but not the trophy, which turns out to hold an inordinate amount of rum punch. It’s just as well there will be no bottom scrubbing at 0630 the next morning. 

Peter_Nielsen2011-thb95x120

Peter Nielsen, SAIL’s Editor-in-Chief, is

hooked on Caribbean cruising and racing

Bareboat Racing 101

• There are three regattas with strong bareboat classes. They are (in 2014) the Heineken Regatta in St. Maarten (March 6-9), BVI Spring Regatta (March 31-April 6), and Antigua Sailing Week (April 26-May 2).

• Check regatta websites for information on charter companies. Sunsail and The Moorings offer race packages, and other companies—notably Marinemax and BVI Yacht Charters—also allow their boats to race.

• You will typically have to put down a $5,000 security on the boat. Some canny skippers insure that bond.

• Bareboat racing is just that—stock charter boats. No spinnakers or poles are allowed.

Contact: Sunsail Yacht Charterssunsail.com

Club Challenge

The International Yacht Club Challenge, sponsored by Sunsail, is a unique race-within-a-race that pits yacht club teams from around the world against each other on matched Jeanneau charter boats. For more information call 877-799-3675, bvispringregatta.org/iycc-invitation

Do you want to read about more charter destinations? Try another story.

• If by Land

• Thin-Water Paradise

• A Boat of Their Own

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