Some of the best sailors in the world make their way to the island every summer for Nantucket Race Week, a nine-day event held every August. Co-hosted by the Nantucket Yacht Club and the Great Harbor Yacht Club, the races and social events that comprise race week raise money to support the Nantucket Community Sailing Center and its efforts to teach and promote sailing.

The two most prominent races are the IOD Celebrity Invitational Regatta and the Opera House Cup. The IOD pits 14 One Design International class sailboats against each other over two days of racing aboard 33-foot boats.


The Sumurun won last year’s Opera House Cup.

“They are thoroughbred racing machines sailed with crews of five people,” says Diana Brown, the executive director of Nantucket Community Sailing.

The catch is that each team gets to sail with a luminary from the sailing community on board as tactician. These include past America’s Cup competitors, Olympic team sailors and former college sailing All-Americans.

The Opera House Cup Regatta consists entirely of antique wooden sailboats. Last summer, 48 classic boats presented a spectacular profile of old-school craftsmanship and sailing skills as they competed in the waters around Nantucket. Last year’s winner, the Sumurun, is a 94-foot ketch built in 1914.

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