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Friday 11th August 2023

When Rob and Theresa Roden chartered a boat in the Caribbean for their honeymoon in 1995, the couple fell in love with Antigua and Barbuda, their people and their culture. Rob Roden, a surfer in his early days and later an avid boater, saw the similarities between Sag Harbor and English Harbour in Antigua, ports both world-renowned for their rich nautical historical significance and modern yachting convenience.

From that, he envisioned an event that would bring the distant ports together and thus, along with the help of the Honorable John Maginley MP, Antigua and Barbuda’s minister of tourism and civil aviation — the Antigua and Barbuda Hamptons Challenge.   Since the inaugural regatta in 2012, those who have won the Antigua and Barbuda Hamptons Challenge have taken home the prize billed as the biggest of its kind on the East Coast: a week-long, all-expenses paid trip for the winning captain and five crew members to participate in Antigua’s Sailing Week. The package includes airfare, all-inclusive accommodations and the use of a sailboat to compete in the week — which will be April 27 to May 3 — all provided by Antigua and Barbuda’s ministry of tourism.

Following the sudden death of her husband in August 2018, just one week before the regatta he helped to create was scheduled to take place, Theresa Roden has taken the reigns of the event and has continued to steer the ship, so to speak, which continues Saturday, August 12. The regatta carries even more significance to her as the Antigua and Barbuda Hamptons Festival, which makes it an all-day event, doubles now as a fundraiser for her organization, i-tri, an empowerment program for adolescent girls on the East End of Long Island.

The festival, hosted this year under the tent at Marine Park on Bay Street in Sag Harbor, will include a Caribbean-themed party and craft fair that kicks off the day and runs from 10 a.m. to 3 p.m. The skipper’s meeting, hosted by the Peconic Bay Sailing Association, will be at 11 a.m., with a scheduled noon start time for sailing. The post race party, which anyone can purchase a ticket for, will begin at 5:30 p.m., and run until 8 p.m.

It’s at the post race party where the winner of the ultimate prize is announced. Last year’s victor was Big Boat, captained and owned by Breakwater Yacht Club Commodore Bud Rogers. On Sunday, Rogers recalled that he and his crew “were a little bit lucky, but we sailed fast.”

“There were a number of other boats out there. Noyack Bay can be a little complicated, but Cris Brodie, our tactician, kept us going in the right direction,” he said. “Steve Kenny and his boat Gossip were our main competition, but we managed to sneak over the finish line before them. Of course, with all of the different boats in the race, you really don’t know you’ve won until it’s all over.”

A single handicapped race using ratings provided by Performance Handicap Racing Fleet of Eastern Long Island, an overall winner cannot be determined until all boats return. Results are tabulated at the end of the race based on a formula that takes each boat’s handicap into account. Rogers said this is similar to the weekly Wednesday night sailing events at Breakwater Yacht Club.

When it was announced that Rogers and his Big Boat crew had won, to say there were some happy people would be an understatement. Sarah Nightingale was a part of the crew and almost couldn’t believe it.

“How lucky was that?” she said this past weekend when recalling the victory. “It was so awesome, so fantastic.”

Nightingale was part of the crew that headed down to partake in Antigua Sailing Week this past May and said it was certainly a memorable trip, one she thinks she would do again, even if it meant paying out of pocket this time around.


Unfortunately for Rogers, with a family event already planned, he couldn’t make the trip with his crew down to the Caribbean, so he had the unenviable task of deciding who to choose to skipper the boat, which is provided by Dream Yacht Charters. Rogers said he took the list of everyone who was part of the winning crew, crossed off everyone who couldn’t make the trip to begin with, then went down another list of people he had sailed with, either regularly or irregularly. Eventually he settled on Seth Barrows.

“He’s a very good sailor,” Rogers said. “He was the right choice to be the skipper for that regatta.”

“My gosh, what a great experience,” Barrows said. “Just the build up to it, the fact that the prize alone is to an all-inclusive in Antigua, and then Theresa’s foundation behind the cause, it’s just a joy.

“I want to go every year,” he said of Antigua’s Sailing Week. “It’s a great island, it’s a great country. The way it’s all set up, it’s very well organized and it was a lot of fun.”

“I love that kid, he’s so awesome,” Nightingale said of Barrows, whom she sailed with in Antigua. “He’s so young, but such a great leader for us.”

Nightingale explained that a lot of the boat crews wore similar clothing to distinguish themselves from each other, which is how she would tell them apart when talking about them with someone. “Oh, there go the blue hats.” Or, “there go the red hats.”

Nightingale and the crew that went down to Antigua would hang out at a local watering hole in the harbor there, the Loose Cannon Beach Bar. Someone bought a shirt, which was bright orange, easy to pick out while on the water, so Nightingale decided that everyone should buy a shirt, and they would be the “orange shirts.”

“We kind of took on that Loose Cannon identity,” she said, with a laugh. cause of another commitment, Rogers won’t be able to helm his own boat this time around, so it’ll be up to the crew who will be on hand to try to get back to Antigua.“We’d love to repeat,” Rogers said. “But it depends on a lot that happens between now and then. Either way, it’ll be a lot of fun.”For more information, to sign up for the regatta, or to purchase tickets to the post-race party, visit For more information on Antigua Sailing Week, go to

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