When million-dollar mega-yachts, Alerions and the occasional J-Class sailboat fill up Nantucket Harbor, some of the most competitive sailing can be found outside the Jetties, on $500 Hobie Cats. The fleet isn’t part of the Nantucket Yacht Club or the Great Harbor Yacht Club, but the Royal Nantucket Yacht Squadron, where the only dues to join are $50 and a 12-pack of beers.
“It’s exactly what sailing and racing should be,” said Jon Beery, a member of the Royal Nantucket Yacht Squadron—the beer league of Nantucket sailing. “I’ve sailed my entire life, and in racing you have two avenues. There are people who are very hardcore and rules oriented, and this is fundamentally opposite.”
On some Thursday nights, the Royal Nantucket Yacht Squadron has boasted more than 50 members. On some nights, only a handful of members show up to race on two or three 16-foot Hobie Cats—possibly the furthest thing from luxury sailing there is. When they’re out on the water, they’re sailing over 20 knots—fast enough to be considered some of the most competitive racing around, but casual enough for crew members to underhand-toss light beers to each other from a cooler.
“We could bump into each other and do $200 worth of damage, versus $200,000 worth of damage [on an Alerion],” said Brian Sager, who co-founded the Yacht Squadron in 2020 with Joe Lloyd. “It started attracting people. We started telling people to come on down to Jetties Beach with a 12-pack of beer. Some people took it seriously and some took it very informally, but it kept growing to the point where we had eight or nine boats racing. People asked what we were doing, and we would say it’s the most exclusive club on Nantucket.”
As the Royal Nantucket Yacht Squadron started to attract more interest from sailors, Sager and Lloyd didn’t hesitate to welcome them aboard, as long as those new members brought a 12-pack of beer. With the group growing, its members started assigning titles to each other, all to make the group sound official. Sager—a talented sailor in his own right who has raced on big boats like
Outlier
and spent a few years coaching the Nantucket High School sailing team with Lloyd—spent a year as the Yacht Squadron’s commodore. His current title is rear admiral, a title without responsibilities.
Sometimes the catamarans would capsize inside the harbor channel too close for comfort to the passing ferries. One time, a crew member was “launched like a trebuchet,” Sager said. She climbed back on board and had a beer.
“There’s no serious attempt at maintaining the rules, but everybody has to know the rules and know when they’ve fouled,” said Posie Constable, a member of the Yacht Squadron. As Beery puts it, “It’s competitive fun racing but at the same time it’s chill. We enforce the rules but we don’t get angry on the water and if someone does, the person who does get angry is the one who’s in trouble.”
At the end of every season, the Royal Nantucket Yacht Squadron awards one member of the fleet with a brass cannon with a scrimshaw engraving, the group’s equivalent of a trophy. But this trophy is not given to the member with the most victories or the single fastest time. Instead, it’s given to the crew member who recruited the most members over the course of the summer.
Beery, who purchased his Hobie Cat for just $500 with a “hole on the side and a bent mast,” won the trophy several years ago. He couldn’t recall exactly when he won it. The group doesn’t always keep track of when awards were won, and that’s the point. While the racing is competitive, the whole idea is to sit back with your friends while you’re out on the water, crack open a beer and race back to the beach. “We all rally together, no one has deep pockets,” Beery said. “But we do have professional sailors and some of the top racers are out on the water with the RNYS.”
