The Antigua & Barbuda Hamptons Challenge Returns!

What happens to a dream deferred? Some dry up, it is said, like a raisin in the sun. Others wait a year for another crack at it. Such it is with the dream of winning the biggest sailing prize on the East End. And in a few short weeks, boats from yacht clubs across Long Island will unfurl their sails with visions of taking the trophy (and the grand prize, but more on that later) in the second annual Antigua & Barbuda Hamptons Challenge—a sailing regatta borne of a blend of competition and Caribbean culture—in Sag Harbor on August 17.

“Last year’s event was such a success, we had 25 boats and it was a great time, so our expectations are higher this year,” says Antigua-Barbuda Tourism Minister John Maginley, filled with excitement about merging the sailing passion of the East End with the rich maritime tradition of his Caribbean home. “We are looking forward to expanding on that—in the race, but also in becoming even more a part of the Hamptons community and contributing in a variety of ways.”

The goal of the first Antigua & Barbuda Hamptons Challenge was to build for the future: in the sailing community, on the tourism front (“Hamptons in the summertime, Antigua the rest of the year” has been one of Maginley’s favorite mantras) and with the community at large here on the East End. Continuing that tradition, regatta organizers are particularly focused on the event’s support of two local charitable organizations—the Breakwater Yacht Club’s Junior Sailing Program and the I-tri Transformation Through Triathlon.

With iTri, the philosophy is rooted in teaching sixth, seventh and eighth grade girls skills in setting goals and working to achieve them, in athletic arenas and in all aspects of life. Sailing, Maginley believes from having seen its benefits from the time he was a youth in the Caribbean, offers much more than a nice day out on the water. It’s the work and dedication it takes to learn a skill, to find a balance and harmony between oneself and nature, and to learn how to handle unpredictable situations.

There are many luxurious sailboats cutting through out local waters, the kinds that turn heads and inspire audible oohs and aahs. But you don’t need to own one to enter the race. The Antigua & Barbuda Hamptons Challenge is open to monohull sailboats no less than 22 feet LOA (length overall) and a PHRF of 200 or less. For those who don’t speak sailing-ese, that’s Performance Handicap Racing Fleet, a handicapping system that allows boats of different classes to compete against one another—in this case, for bragging rights and glory, but also something much larger, a prize you won’t find anywhere around here.

As with last year’s winner, Jim Ryan—vice commodore of the Peconic Bay Sailing Association and one of the key race organizers from the start—the skipper of the winning boat and six crew members this year will be sent to compete in Antigua Sailing Week 2014, one of the biggest sailing events in the world. The flights, accommodations, entry fees, even a yacht, are included, along with the chance to experience island-style sailing culture.

Antigua Sailing Week is an international gathering of top sailors and people coming to celebrate the sport. It’s “five days of racing and five days of partying,” Maginley says, and that’s the atmosphere he looks forward to creating here. The 2012 Antigua & Barbuda Hamptons Challenge after-party was a reggae-music-and-libation filled affair.“This year we’re going to bring a little bit more of the Caribbean festival feeling to the after party, bring a little Antigua and Barbuda up here. This is going to be even more of a party.”

For more info, go to visitantiguabarbuda.com and antiguabarbudahamptonschallenge.com.