A Hamptons Regatta by Way of Antigua and Barbuda

The maritime history of the East End is a rich one, filled with legends of pirates and whalers from days gone by, tales that have given way to stories now shared by locals and tourists alike about the it-was-so-big-you-won’t-believe-it yachts that pull into marinas along our shores. For all that, though, there has been a decided lack of lore surrounding modern-day sailors.

At the American Hotel in Sag Harbor, close enough to the namesake waters to catch a waft of salt in the air, Antigua and Barbuda Minister of Tourism John McGinley is discussing the event that is changing that—the Antigua and Barbuda Hamptons Challenge sailing race. Thinking back on the day two years ago when “I sat in this same hotel, figuring out how we could get this Antigua and Barbuda thing going in the Hamptons,” he admits he was hopeful, but not entirely sure what to expect.  “It worked out a lot better that we imagined,” he admits.

Some 25 boats signed on last summer when the inaugural Challenge set sail from Sag Harbor’s Breakwater Yacht Club, with Jim Ryan and the crew aboard Wasn’t Me emerging victorious. Perhaps more surprising that the instant popularity of the event was the fact that there was, and remains, nothing like it on the East End.

“Nobody could believe the Hamptons didn’t have a regatta before,” Maginley says with a sense of genuine wonder. “It’s strange that for all these years, with so many sailors and yacht clubs here, that they never got together to have a regatta. Well, we changed that.”

This August, the second annual Antigua and Barbuda Hamptons Challenge will again turn the waters off Sag Harbor into one of the most significant sailing destinations in the world. For one day, boats from yacht clubs and sailing associations that are part of the Eastern Long Island Yachting Association will compete for one of the top prizes of any regatta in the Northeast: the winning captain plus up to six crew members will be flown, all expenses paid, to the Caribbean next year to compete in the 2014 Antigua Sailing Week, one of the world’s most prestigious sailing events.

The size of the field, on the other hand, will dictate the future. “We would like to grow—if we get up to 50 boats this year, we’ll be doing very well,” Maginley says. “We just want to race to continue to get bigger, for the people of the Hamptons and the East Coast of Long Island to take an active part in it. And they will. Many, many people, not only in the sailing community but the community in general, say they want to be part of this.”

That is a testament to the underlying philanthropy of the race. Since Maginley and Captains Guide magazine publisher Rob Roden conceived of the regatta, the goal has been not only raising the profile of Hamptons sailing, and raising awareness about the cultural offerings of Maginley’s island home, but also raising funds to support the Breakwater Yacht Club Junior Sailing Program and i-Tri, an organization that helps teach at-risk girls discipline, teamwork and self-respect through triathlon training.

This charitable aspect, the potential to reach deep into the heart of the community, is important to Maginley, as the similarities between his island home and this island are not lost on the minister. “People who come to the Hamptons are often people who are leaving the madness of Manhattan and other places to get away—it’s close to the ocean, it has a simplicity to it—and we have the same type of thing in Antigua. Sailing is a way to bring these two places together. ”

The 2013 Antigua & Barbuda Hamptons Challenge will be held Satruday, August 17. For more information, including a schedule of events and the Notice of Race, visit antiguabarbudahamptonschallenge.com and breakwateryc.org. To read more about Antigua Sailing Week and Antigua-Barbuda, go to visitantiguabarbuda.com.