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CREEEEEEEEEEK.

Five heads snap toward the boom as an eerie sound emanates from the gooseneck on our Freedom 30. There were once four bolts binding the boom to the fitting, but now only two remain, and, judging from the groans of the metal-on-metal joint, this is one marriage that will likely be separated by death. And soon.

“Traveler up, main out two inches,” barks Rod Johnstone. I glance over at our skipper. It’s obvious that he’s weighing the benefits of good sailing strategy against the prospect of mechanical failure. The Caribbean trade winds are blowing a constant 15 knots, and two other Freedom 30s, one skippered by boat designer Bruce Kirby and the other by Olympic great Keith Musto, are in close pursuit. Our boom may be self-destructing, but our skipper isn’t about to concede defeat. After all, we handily won our class’s morning distance race from the Bitter End Yacht Club to The Baths, on Virgin Gorda’s southwest coast, and now we’re on track to top the entire fleet. Provided, of course, our boom holds together. While the annual Pro-Am regatta is about meeting new people and casual racing with the world’s best sailors, there’s nothing relaxed about the rivalry playing out here in North Sound.

The Bitter End Yacht Club (BEYC) is situated on Virgin Gorda’s northern shore on sheltered North Sound, bounded by Prickly Pear Island, Saba Rock, and Mosquito Island. Biras Creek bisects the island’s mountainous rise to the southwest and serves as a constant wind funnel, providing tricky inshore conditions. The clichd descriptions are all accurate: Yes, the water is turquoise; yes, the trade winds blow a crisp 10 to 15 knots all day long; yes, the islands rise like jewels from the sea; yes, the hardest decision you’ll make all day is whether to take out a Laser or a Hobie Wave before lunch. Life can be rough.

What isn’t clichd, however, is the cast of characters who have gathered for the BEYC’s 20th annual Pro-Am Regatta. Many greats, from “Juniors” like Russell Coutts and Paul Cayard to “Masters,” whose ranks include Lowell North, Rod Johnstone, Butch Ulmer, and Bruce Kirby, are on hand, eager to participate in four days of casual racing and socializing with the “amateurs,” many of whom are excellent sailors in their own right.

“There are plenty of professional sailors who aren’t nice people,” said John Glynn, the BEYC’s Director of Public Relations and Special Events, one morning before racing. “And they don’t get invited to the Pro-Am. We give invitations only to people who are not only great sailors, but also excited about sharing what they know.” Glynn’s words prove true. Where else can a visiting sailor sit beside the Curmudgeon himself (Tom Leweck) at breakfast, get invited to sail with racing great Lowell North in the morning, crew for Dawn Riley in the afternoon’s fleet racing, and then enjoy drinks with everyone in the evening?

As exciting as crewing for the pros may be, it is the amateurs who often provide the most entertainment. One of the Pro-Am’s draws is that every Am has a chance to earn a free return trip the following year by winning the Musto Scuttlebutt Sailing Club Championship. As might be predicted, this sub-event has its own set of ringers, many of whom arrive with just one goal in mind: to win a free ride back to paradise the following year.

Take, for example, Chris Fretz from New Jersey. In 2004 he and his wife, Mary, visited the BEYC on their honeymoon, unaware that the Pro-Am was taking place. Chris came close to winning that first year, so they returned in 2005. The second year he was successful, and now, in their third consecutive year, they are enjoying the benefits of last year’s victory. But Chris is a racer’s racer and already has his eye on next year’s vacation.

Enter James from England. He and his wife arrived at the Bitter End on their honeymoon (they were on a charter), content to cruise for a week and also unaware that the Pro-Am was unfolding that same week. “My whole world is sailing,” James said one night over dinner. “So you can imagine my surprise when I arrived and saw Paul [Cayard] sitting with his wife and daughter. Then I saw Rod [Johnstone], and I knew something was up.” While James might have been caught unaware by the club’s guest list, he was more than prepared for the Musto Scuttlebutt championship, in which he placed well during the first few days, even though he wasn’t, as normally required, a BEYC guest (the club is generous when it comes to sailing). A friendly competition unfolded between Chris, James, and Jim Durden, a Martin 242 sailor from San Diego, but this didn’t keep these foes on the course from having multi-hour dinner conversations that encompassed all aspects of sailing.

Considering the fact that James’s new wife planned the entire honeymoon, plus the fact that she doesn’t race, it’s safe to say that their marriage is off to a good start. Short of honeymooning in Valencia, Spain, in July of 2007, James could not have found himself in better sailing company.

“So, is this your first year at the Pro-Am?” This is the question everyone asked everyone else during my stay. Further investigation revealed its source: Many of the Ams are returning veterans, lured back by the promise of perfect sailing conditions, the opportunity to learn from the world’s best sailors, the chance to socialize with other amateurs from around the world, and the magical experience that is the Bitter End’s trademark. Several of them have crested the one-decade mark: Jibby, a Yngling sailor from New York, has been a repeat customer since 1989; Linda, from St. Louis, is celebrating her twelfth Pro-Am. Even among the Pros I sensed a certain hint of legacy as they recalled the fun of previous years.

The Pro-Am encompasses fleet racing, distance racing, and match-racing events. Many of the returning Ams already have their schedules planned out, and it soon becomes obvious who has this event dialed in and who is experiencing it for the first time. “The best part about sailing with the Pros is watching them screw up,” says Chris Fretz. “You don’t learn much when everything goes well because they have things under control. It’s when they have a bad start or blow a layline that you learn the most. Seeing what they do to reel in their boats—that’s what I love most about this event.”

Apparently this apprenticeship paid off, as Chris managed to beat out Jim by a mere point for the winning ticket to the 2007 event. There were handshakes and smiles all around, the runner-up (Jim) was awarded a beautiful Corum watch, and the unofficial bronze-medal winner (James) took home his lovely bride with a fantastic sense of vacation planning. When everyone emerges a winner, the normal boundaries of competition collapse, replaced with a sense of sharing that is rare in the world of competitive sailing.

Tink. I watch with a sinking feeling as one of the now-sheared bolt heads plunks onto the deck, bounces once, and tumbles overboard. A mere half-mile separates our tired rig from line honors, but this glorious outcome is hardly certain; a quick glance astern reveals Keith Musto’s Freedom 30 just four boatlengths behind us, with Bruce Kirby’s bow an equal distance behind Musto. I know that if the bolts sheer, our heady lead will dissolve into the Caribbean ether.

“Let me know if Musto tacks,” Rod says, not taking his attention off his task as skipper for a second. His eyes automatically glance from mainsail to jib to horizon, seeking any subtle change that might further threaten our delicate fitting. I death-grip the mainsheet, waiting to bleed slack if necessary. The separation between the boom and the gooseneck is now so great that I could pass my entire hand through the opening, and I know that if it weren’t for our unconventional use of upwind boomvang pressure, our boom would likely be joining the bolt head at the bottom of the sea.

BAM! The gunshot ricochets around the protected bay, and cheers erupt from our crew. I glance over at Rod, who is obviously pleased with his crew’s performance. “Let’s get that main down,” Rod says, the grin still fresh on his face. “The boom doesn’t owe us anything else.” With that the sail is lowered, the iron genny is fired up, and our intrepid crew retires to the bar for mudslides (Rod’s favorite), beer (the crew’s favorite), and a happy recap of the day’s event. That is, until someone mentions that there are still three more days of racing. Then all attention inevitably turns to Pro-Am veterans to get the scoop on tomorrow’s activities. We clink glasses and savor the fact that here, at the Pro-Am, all sailors emerge better off than when they arrived, bolstered by the experience of sailing with their heroes and by the friendships they form.

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