Inaugural St. Maarten Hamptons Sailing Cup Arrives in Sag Harbor

Regatta Sailing Boat
Come sail away...maybe all the way to the Caribbean! Photo: duha127/iStock/Thinkstock


Few sights on the East End compare with the colors of wind-filled sails unfurled against a late-summer sky, sun glinting off the surf as boats cut through the water. It fills onlookers and participants alike with a sense of freedom and adventure and the promise that open water holds. Indeed, sailing has an emotional resonance here in the Hamptons, particularly when more than a nice day on deck is at stake—as it is this weekend. One of the biggest sailing prizes in the Northeast is up for grabs in the waters off Sag Harbor when the inaugural St. Maarten Hamptons Sailing Cup goes off this Saturday, September 6, from the Breakwater Yacht Club.

Of course, mariners from across Long Island will want the bragging rights that come with victory in a local regatta, not to mention the trophy that will grace their own yacht club for a year. But let’s be honest, bragging rights only get you so far. Winning this regatta will get you a little farther—the Caribbean. The grand prize in the St. Maarten Hamptons Sailing Cup is an all-expenses-paid trip for the captain and a crew of six to the island of St. Maarten to sail in the 2015 HeinekenRegatta.

For more than 30 years, the St. Maarten Heineken Regatta has drawn sailing aficionados from around the globe with the island’s beautiful waters and prime sailing conditions, not to mention the celebratory atmosphere surrounding the event. Taking the regatta’s original tagline, “Serious Fun,” to heart, what began with just a dozen boats in 1980 has evolved to include hundreds of competitors from points as diverse and Russia and Brazil, along with thousands of spectators and revelers who come to the island to enjoy the many parties—which have featured such musical talents as the Black Eyed Peas, the Marley Brothers, Maxi Priest and Wyclef Jean.

“There’s no other prize like this around here,” says Captains Guide magazine publisher Rob Roden, whose long-held passion for sailing and bringing a regatta to the Hamptons helped make the St. Maarten Hamptons Cup a reality this year. And any boat that enters has a true chance to grab the brass ring, as all yachts will be scored using Time on Time—using the Eastern Long Island Yacht Association (ELIYA) Scoring Formula. For the purpose of explanation to landlubbers, this is essentially a handicapping system that applies a mathematical formula by which boats of varying sizes can compete against one another. In evening the playing field, it gives smaller vessels a shot at the big time.

And this is big. “They get flights, accommodations, entry fees and a yacht provided to race down there. This is the largest amateur sailing prize on the East Coast, and it’s happening right in our backyard,” Roden says. The event also helps two youth groups in that same backyard. Monies raised will go to support both the Breakwater Yacht Club Junior Sailing Program and i-Tri Transformation Through Triathlon, which works with adolescent girls on the East End in teaching self-esteem through athletic training and teamwork.

Once the race is done, it’s off to the Breakwater Yacht Club for the post-race party. In an island-inspired celebration where steel-drum music will be playing, drinks will be flowing and the anticipation will be growing as everyone awaits the moment that the grand prize winner is announced, the Hamptons and the island of St. Maarten will be connected by a spirit of “serious fun” that only sailing can create.

The inaugural St. Maarten Hamptons Sailing Cup will be held on Saturday, September 6, at 11 a.m. The public is invited to attend the post-regatta celebration at 5 p.m. at the Breakwater Yacht Club (15 Bay Street) in Sag Harbor. Party tickets are $45 in advance or $50 at the door. For more information on the party and the regatta, visit

More from Our Sister Sites