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.