A Pair of Prizes, Surprisingly, Are Won at the 13th Annual Antigua and Barbuda Hamptons Challenge Regatta

Those who competed in the 13th annual Antigua and Barbuda Hamptons Challenge Regatta on Saturday saw just about every type of sailing conditions that could be had.

The race, hosted by the Peconic Bay Sailing Association and billed as the biggest of its kind in the Northeast with the grand prize a weeklong, all-expenses paid trip for the winning captain and five crew members to participate in Antigua’s Sailing Week, started under blue skies with typical southwest winds ranging from 8 to 12 knots. More than halfway into the race, clouds rolled in, eventually creating a totally overcast sky. Then, 10 minutes or so before the race ended, the sky grew dark when torrents of rain fell. Halfway back to Sag Harbor, onboard the VIP chase boat, the 50-foot yacht Jubilance, the sun reappeared to great applause.

Then the real fun began.

The post race party — the back end of the Antigua and Barbuda Hamptons Festival, a daylong celebration of the regatta — is where the winner of the ultimate prize is announced. Since the regatta is a single handicapped race using ratings provided by Performance Handicap Racing Fleet of Eastern Long Island, an overall winner is not 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.

When all was said and done and the results were finalized, it was Lunatic Fringe, owned and skippered by Bill Lehnert and crew out of Old Cove Yacht Club in New Suffolk, was declared the winner. Lehnert, whose daughter, Breckin Lehnert, was given the Rob Roden Memorial Award in honor of the crew having the most fun during the race, and his crew were the winners of the package that includes airfare, all-inclusive accommodations and the use of a sailboat to compete in Antigua’s Sailing Week — which is April 27 to May 3 — all provided by Antigua and Barbuda’s ministry of tourism.

The Antigua and Barbuda Hamptons Challenge was created in partnership between Antigua and Barbuda’s ministry of tourism and Rob and Theresa Roden. After the untimely death of her husband in August 2018, Theresa Roden has taken over and the event now doubles as a fundraiser for her organization, i-tri, an empowerment program for adolescent girls on the East End of Long Island.

To that end, this year’s theme of the post race party was about female empowerment, additionally fueled by the fact that Antigua has had a pair of triumphs for its own women recently. Last month, Team Antigua Island Girls, an all-female rowing team from Antigua and Barbuda, became the first all-female, Black team to row across the Pacific Ocean as part of the inaugural 2023 Pacific Challenge, a feat that included spending 41 days crossing the Pacific Ocean, covering approximately 2,800 nautical miles beginning in Monterey Bay, California, and finishing in Kauai, Hawaii.

More recently, on August 10, Keisha Schahaff and her daughter Anastatia Mayers of Antigua and Barbuda made history when they traveled to space via the Virgin Galactic 02 Spacecraft at the Spaceport America in Truth or Consequences, New Mexico. At 18, Ana is the youngest person, by two weeks, to ever to go to space, and Keisha and Ana are the first mother and daughter and the first people from the Caribbean to make the journey into the cosmos, and only the sixth and seventh Black women to travel to space.

To celebrate the empowerment and success of women, Antigua and Barbuda Minister of Tourism Charles “Max” Fernandez gave an additional special award, complete with its own all-expenses paid trip to Antigua’s Sailing Week, to the boat with a female skipper and the most female crew. That wound up being Faster Pussycat Kill! Kill!, owned and skippered by Beth Fleisher, with crew Caroline and Charlotte Keil, along with Beth’s son, Ben Claremont, all of whom typically sail out of Peconic Bay Sailing Association.

Fleisher met Theresa Roden at the after party, something she made sure to buy tickets for, for herself and all of her crew, and the two got to talking about big boat sailing and how there is a dearth of women who tend to compete in the sport. Roden asked Fleisher to stick around for the awards as she wanted to do a shoutout to her and her crew of nearly all women. Then it was announced that Fleisher and her crew would be going to Antigua, along with the crew of Lunatic Fringe.

“The next thing I know, I hear her giving out this great award to me and my female crew and we’re going down to Antigua,” Fleisher said. “It will just be incredible fun. The water down there is beautiful. I’ve never been there, but I’ve had a bunch of friends go there over the years and Antigua is really a lovely island. The people are wonderful, the racing is incredible and it’s something to look forward to. Charlotte is close to finishing up her college career with one last semester, so she’s got tests and everything going on, but she’s making plans and arrangements going on right now, getting her ducks in a row, and we all plan on making that trip.”

Fleisher, a Brooklyn native who summers in Southold, said she’s sailed the Antigua and Barbuda Hamptons Challenge a few times. What she likes about it is it’s different waters and a different group of competitors than she’s used to on the North Fork. What she also really likes about it is that the race is a fundraiser for i-tri, a cause she feels is very important.

“Obviously, as a woman who has been engaged in competitive sports my entire life, I’ve seen the benefits of being engaged in sports,” she said. “It’s very, very important for girls, and women, for building self esteem, self confidence, and getting to know your body and getting comfortable with it and how strong we truly are. It’s really only a benefit as you move forward in the world.

“So am I secretly proud to have competed in this race with these young women going up against a lot of these boats captained mainly by a bunch of men. You betcha!” Fleisher added. “It’s a sport that is so dominated by men, but last year we won our series at PBSA and regularly do really well. We just love that women empowerment and we embrace our pink. We wear hot pink vests. Barbie ain’t got nothing on us.”

Roden said it was a fantastic way to end what was an overall great day.

“It was an incredible day and night,” she said. “We are grateful for the wonderful partnership we have with the Antigua and Barbuda tourism ministry and the sisterhood we have between the ports of Sag Harbor and English Harbour.”