NANTUCKET RACE WEEK

Nantucket Race Week is eleven days of sailing in August off the island of Nantucket, twenty-six miles out from Hyannis, in the six-mile harbour and on Nantucket Sound beyond it: youth racing first, then the island’s one-design fleets, a women’s regatta, a celebrity invitational and the two-day Nantucket Regatta, and on the last Sunday the Opera House Cup, for classic yachts with wooden hulls. It is run by Nantucket Community Sailing with the island’s two yacht clubs, the Nantucket Yacht Club and the Great Harbor Yacht Club, and raises about a quarter of the charity’s yearly budget.

The Opera House Cup began in 1973 as an informal race to cheer up a widow, and its first trophy was an old champagne bucket.

The Champagne Bucket

In 1973 a group of island sailors gathered at the Opera House Restaurant, where its owner, Gwen Gaillard, “was holding court”. She had just lost her husband, and the sailors decided on a race to cheer her up. They all had wooden boats, and many were living on them. Nine boats were in the first race; the scoring was done by a participant’s wife who was good at mathematics. Mariner, a fifty-four-footer built in 1950, won it, sailed by Henry and Bob Tiedemann, father and son, and Gaillard put the winner’s name on a wooden plaque on the wall. The restaurant has since closed.

The organisers call the Cup the first all-wooden, single-hulled classic yacht regatta on the East Coast, and the grandfather of all wooden boat regattas. Today a boat must have a hull of wood, or of cold-moulded wood, and be at least twenty-four feet long to race for the Cup; others may be asked into a division of their own. Intrepid, Weatherly and Columbia, each a winner of the America’s Cup, have sailed in it.

Race Week grew around the Cup. The Nantucket Yacht Club put on a 12 Metre regatta as a prelude to it, then a handicap race, then racing for the International One Designs, for juniors and for the one-design classes, and a celebrity invitational, and in time all of it was combined as Race Week. Nantucket Community Sailing, founded in 1994 by island educators, sailors and community leaders, counts it among its signature events, and it is the charity’s largest fundraiser.

The island raced long before the Cup. By the summer of 1906 a group calling itself the Nantucket Yacht Club was holding races off Brant Point, and the Rainbow Fleet dates to the 1920s: catboats with coloured sails, which grew out of the club’s search for a boat for children to learn in. A postcard of 1929 shows them being towed round the point in a dead calm.

The Pursuit

There are two waters. The harbour is six miles long, with tricky currents and ever-shifting sandbars; the Sound has deep water, subtle currents and a consistent sea breeze. The youth series opens the week in Club 420s and Optimists. From the first Saturday the island’s ten one-design classes race, from Beetle Cats to the International One Designs, with kiteboards and wing-foilers among them. The Women’s Regatta follows midweek, and on the second Thursday the Celebrity Invitational puts guest tacticians aboard, “America’s Cup legends, hall-of-famers, and world champions”.

The Nantucket Regatta takes the Friday and Saturday on the Sound: keelboats of twenty-two feet and over, classic wooden boats, spirit-of-tradition yachts and modern racer-cruisers, with 12 Metres and TP52s in classes of their own and the schooners on a course apart. On the Saturday evening the classic yachts lie at the docks of the Nantucket Boat Basin, and the public may go aboard.

On the Sunday morning, at nine, the fleet parades past the lighthouse at Brant Point, and the Rainbow Fleet sails round it, before a crowd of fifteen hundred or more, an announcer and a printed programme. Then the Cup is sailed on the Sound with a pursuit start: the lowest-rated boats go first, so that in principle every boat should finish at the same time, over a course of eleven to twenty-three miles as the wind allows. Two winners are declared, the first boat home and the first plank-on-frame boat home. In the evening the awards are given at a party on Jetties Beach, “often called ‘the party of the season’”.

In 2026, its twenty-third year, Race Week ran from 6 to 16 August. The fifty-fourth Opera House Cup waited some hours for wind, several sailors of the Rainbow Fleet paddled and were towed round the lighthouse to keep the tradition, and Sea Horse, sailed by Ronald Zarrella, won it again. A new Lighthouse Trophy, after the Great Point Lighthouse, was given for the first time to the boats without wooden hulls.

What to Know

It runs through the middle of August and ends with the Opera House Cup on the last Sunday; in 2026 it ran from a Thursday to the Sunday of the following week. The 2027 dates have not been announced.

The parade at Brant Point is free to watch from the beach; from the water, boats must keep outside the racecourse. The awards party is for competitors, sponsors and invited guests; in 2026 each Cup entry, at five hundred dollars, carried two tickets.

Nothing is published, for the racing or for the party. A navy blazer and soft soles by day, on the docks and aboard; a lounge suit without a tie for the evening on the beach.

The ferries run from Hyannis: two hours and a quarter on the traditional boat, an hour on the fast one, which should be booked well ahead for August weekends. Nantucket Memorial Airport, three miles from the town, has seasonal flights from LaGuardia, Kennedy, Newark and Washington National, and charters from Teterboro and White Plains. The White Elephant on Easton Street has stood on the harbour since the 1920s; staying in the town puts the docks and Brant Point within a walk.

The mistake is to wait for the start. The sight is the parade of yachts past the lighthouse at nine, before the fleet goes out to the Sound, and the start itself waits on the wind.

The Court

Nantucket Race Week is not the Court’s own. A place aboard a classic yacht for the parade and the Cup, and tickets to the awards party, are sought on a member’s behalf, and the Court arranges the whole of it: getting there, where to stay in the town, and the table afterward. The Court is on the water out of Sag Harbor the same month, for the Harbour Lunch.

How one becomes a member is set out under Admission.