Years from now, a crowd will be gathered at the Sag Harbor waterfront on an August afternoon, marveling at a parade of sailboats and cheering their favorite onto victory in yet another running of the Antigua-Barbuda Hamptons Challenge. It may be the 10th or the 25th anniversary, but somewhere in that crowd you’ll hear voices talking about the first time they saw this race. You never forget your first time.
The 25 boats that made up the inaugural Antigua-Barbuda Hamptons Challenge regatta set sail from the Breakwater Yacht Club amid rainy skies and fickle winds this past Saturday, but in the glow of the awards party back at the yacht club hours later, reggae band in the background, you’d never know the day was awash in anything but Caribbean-worthy sunshine. “No matter where those spinnakers fly, it’s always beautiful,” said Antigua-Barbuda Minister of Tourism John Maginley, and nobody in the onlooking crowd could argue. “Everybody came home safely, yeah? We haven’t lost anybody? Then we’ve had a successful race.”
Those are fine standards, to be sure, but the bar set by Maginley and Captains Guide magazine publisher Rob Roden when they conceived of the Antigua-Barbuda Hamptons Challenge last year were far loftier. “We set out to combine Antigua and Barbuda with the Hamptons,” said Maginley. What they dreamt of was a race that would promote East End sailing and the sailing haven that is the Caribbean country, then linking those two cultures beyond the rigging and mainsails.
“Hamptons in the summertime, Antigua the rest of the year,” Maginley says. “That’s what we’ve been saying all along.” The first ambassadors of that notion are the recipients of the regatta’s top prize—an all-expenses-paid trip for the winning captain and six crew members to fly to the Caribbean and compete in Antigua Sailing Week 2013 next spring—and the announcement of that winner was the highlight of the day.
The handicapping system governing the race meant that not only could smaller boats have a chances of upsetting the big boys, but that the first boat to cross the finish line was not necessarily the overall grand-prize winner. Beer and wine and camaraderie flowing at the yacht club gave way to a moment of American Idol–worthy anticipation as Maginley handed out awards to each of the sailing divisions before pausing to reveal the overall champion.
If Maginley ever goes looking for another career, Ryan Seacrest had better watch his back. “Yeah, I tried to add in a little fun, a little suspense to it all,” the Minister admits with a laugh. And when he announced that the boat led by Jim Ryan—the vice commodore of the Peconic Bay Sailing Association and one of the key race organizers from the very beginning—had earned top honors, cheers exploded.
Even some 15 minutes after jumping up-and-down with such enthusiasm that his phone popped out of his pocket, Ryan was aglow. “I’m shocked. I’m ecstatic. Ultimately, I guess I got lucky. I sail any time I’m not working. Literally. I sail all winter long, I sail every Wednesday and Saturday and Sunday in the summertime. And this is special. It was a tough day out there. I was shivering at one point—it was cloudy, it was raining, I was in shorts. We came into the party and everybody said, ‘You did well.’ But I’ve heard the “you did well” thing before. And when it comes to the big trophy it’s Ooooohhhhh…you came in second. But not today.”
With the sun starting to set over Sag Harbor, Maginley finally takes a moment to sit and reflect on it all. “When you come up with an idea and start working on it, you always think, I hope this works and doesn’t fall flat on its face,” he says. He chuckles, but he’s serious. Launching a new endeavor of this magnitude in the Hamptons is no easy task. “Now this is something unique. It’s the only regatta in the Hamptons in the summertime, there’s a prize that nobody else can offer. And when I see commodores of yacht clubs and experienced sailors saying yes, this is something I want to be part of, that’s important.
“Also very important is the iTri Triathlon charity,” he continues, lauding the program that helps adolescent girls build self-esteem and other life skills through triathlon training. “While we’re promoting Antigua, we’re also helping underprivileged girls in this area—there’s a social side to it. So the racers have a good time—and you can see they’re all partying here!—iTri develops and can support the young ladies. And for Antigua and Barbuda, we’re fixing our presence in this community in a very positive way.”
It is a presence the race organizers only see growing. “We had 25 boats this year,” says Ryan. “I see 75 boats next year. Everybody’s going to want in—it’s a huge prize. It’s going to ramp up sailing on the East End dramatically. This is going to be a Hamptons event, like the Hampton Classic horse show. This is something people are going to want to be a part of.”