Down a rickety dock at the Sea Cliff Yacht Club, a pair of motorboats named the Iliad and the Odyssey bobbed in Mosquito Cove, waiting to transport maritime enthusiasts to the finish boat, Breathless, to watch sleek sailboats as they finished the 42nd Around Long Island Regatta, a three-day race that ended in the village last Saturday.
The Iliad, steered by the launch captain, cut across the placid water, past anchored vessels with drawn sails, through Hempstead Harbor in pursuit of Breathless, a beaming white Hunter sailboat with an array of nautical flags. Glen Cove’s Morgan Memorial Park, with its tree-covered hills, was in the background, and farther down shore Sea Cliff’s Victorian mansions dotted the cliffs.
The race, hosted by the Sea Cliff Yacht Club, is designed for sailors of all skill levels, with 10 divisions. There are crews of weekend cruisers, blue-water competitors, academy teams and even a junior- division sailing along a 205 nautical mile course. More than 60 crews took part in this year’s race.
The regatta begins in New York Harbor and heads east past Brooklyn and Long Island’s South Shore, before winding around Montauk, across Gardiner’s Bay, and then into the Long Island Sound, before ending in Sea Cliff, explained Doug Wefer, of Glen Head, who co-chairs the event with fellow resident James Aikman.
“Each leg has its own element of trickiness,” Wefer said.
The harbor start is challenging, and prepares the crews as they head for the Verrazano Narrows and into the Atlantic Ocean. As they follow Long Island’s South Shore, some boats choose the shortest distance, due east, hugging the shore, while others opt for deeper water in search of stronger wind.
After rounding the South Fork, sailors judge the wind, tides, and current as they head northwest to Plum Gut, where they enter the Long Island Sound. For the final leg, the crews rely on reading wind shifts and currents in order to cross the finish line in Hempstead Harbor with the quickest time.
Aboard Breathless were the Kramer and Rasweiler families, of Glen Cove. “This is our first year on the finishing boat,” Cherise Kramer said. “We record as the boats are coming in, so they can be scored accordingly.” Competitors are scored based on their finishing time.
Kramer and her family are members of the Sea Cliff Yacht Club. They aren’t sailors, but as boaters they enjoy the camaraderie the sport inspires among coastal communities, especially during the regatta.
“To watch this event is the coolest thing ever,” Kramer said. “At the end of it, the sailors are battered, they’re coming in from the cold, but the triumph on their faces is so nice to see.”
Wefer’s favorite part of the weekend, he said, is the awards ceremony, when all of the participants come ashore to the yacht club on Sunday night. “We get to celebrate the winners, as well as the experience and the accomplishment of sailing,” he said. “It doesn’t matter whether you win a trophy or not. It’s a big deal to have to sail around Long Island without stopping.”
While aboard Breathless Saturday morning, the Kramers and Rasweilers saw from their starboard side a 37-foot spinnaker sailboat materialize on the horizon, before making its way into Hempstead Harbor from the Sound. As it drew closer, its pink sails whipped in the wind, leading Jordan Kramer, 13, to declare that they were “fluffing too much.” The sailboat, Shadowfox, finished fifth in its division.
As a three-year member of the yacht club’s junior sailing program, Jordan has learned the ins and outs of maritime maneuvers. Her job on Saturday was to communicate with the race committee ashore and sound an air horn when racers crossed the finish line.
“Learning to use the walkie-talkie and see how it all works is a fun experience,” Jordan said. “You have more respect for it.”
Referring to the sense of friendship exhibited by Jordan and the other junior sailors who volunteered, Kramer remarked that they are “as thick as thieves.” Wefer said all of the regatta volunteers demonstrate a deep camaraderie, working around the clock to cater to the sailors participating in the race.
“Of the 65 boats, only two of them are from the Sea Cliff Yacht Club, so we put a very high priority on hospitality,” he said. “It’s an honor to lead the volunteers that make this event a success.”