Age and Beauty: The Opera House Regatta Sings

For fans of classic wooden sailboats, the Opera House Regatta is a feast for the eyes and soul off Nantucket.
Blackfish sailboat at the Opera House Regatta
The Jim Taylor-designed 49-foot cold-molded sloop Blackfish won the Spirit of Tradition class. Roger Vandenberg Photography

This past August, the 52nd Annual Opera House Cup attracted an eclectic mix of 47 beautiful wooden yachts for an 11.3-mile race around Nantucket Sound in Massachusetts.

The concept for this classic-­boat race was hatched in 1973, when Gwen Gaillard, owner of the Opera House Restaurant, and maître d’ Chick Walsh hosted a group of sailors to ­discuss the idea. Legend has it that famous singers such as Frank Sinatra and Judy Garland sang at the Opera House. Well-known patrons have included Senator Ted Kennedy, a long list of prominent writers and, of course, many sailors. Gaillard posted the winning boat’s name on a wooden plaque on the wall.

Sadly, the Opera House Restaurant closed several years ago, but the regatta lives on and often includes excellent racing for 500-plus sailors who are lucky to be aboard one of the yachts. Winning is important, but the larger mission is to celebrate classic yachts and encourage owners to bring them to Nantucket.

The formation of the Opera House Cup took place during a difficult period in America’s history. The Vietnam War was winding down, and President Nixon was the focus of a congressional inquiry. Nantucket seemed a world away, with classic yachts as a celebration of yesteryear. Most of the yachts were in good shape, even though keeping a wooden boat in Bristol condition often requires major intervention every 30 years or so. The first Opera House Cup was won by Mariner, a 54-footer built in 1950, sailed by father-and-son team Henry and Bob Tiedemann. 

Nowadays, on the day before the regatta, the public is invited to view the boats at a Classic Yacht Exhibition. Onlookers also motor around the harbor to get a close look. This year’s exhibition honored distinguished designers whose yachts competed in this year’s race: Olin Stephens, W. Starling Burgess, L. Francis Herreshoff, Nathanael Greene Herreshoff, John Alden, Philip Rhodes, Clinton Crane, Alfred Luders, Jim Taylor, Aage Nielsen, Joel White, Nicholas Potter and Alfred Mylne.  

Opera House Regatta
The 1956 Alden 39 Abigail rounds the mark in close pursuit of the 1957 K. Aage Nielsen 34 Annie. Roger Vandenberg Photography

Many of America’s most iconic yachts have raced in the Opera House. A list of the winners includes 12-Metres: Valiant, Heritage, Intrepid, Weatherly, American Eagle, Gleam and Onawa. Other great yachts that have raced include Ticonderoga, Black Watch, Columbia, Nirvana and Spartan. More recently, a few Herreshoff-designed Alerions—Sea Horse, Owl and Scheherazade—have won the race.

The race committee can set a course ranging from 11.3 miles to 23.4 miles, depending on the strength of the wind. This year, the course was short because of forecast light 5- to 8-knot winds. At the start, racers crossed the line depending on their handicap rating. The lowest-rated boats—in this case, the International One Designs and Alerions—started first. For the next 1 hour and 6 minutes, yachts crossed the starting line. The theory is that every boat should finish at exactly at the same time. 

Theories are good on paper but not always in practice. Unfortunately for the larger boats, the wind was considerably lighter by the time they started. Sea Horse, skippered by Ron Zarrella with crew Chris Magee and Courtney Koos, rounded the first ­turning mark in third and sailed fast on the 3.1-mile ­upwind leg to take the lead. The Sea Horse crew was the first in the history of the Opera House Cup to be the overall winner two years in row.  

Opera House Regatta
Dorade passes the Great Point Lighthouse in the 2023 OHC. Roger Vandenberg Photography

An exhausted but happy Zarrella told the press after the race: “Doyle Sails did a terrific job with new sails. We had the boat hauled, the bottom burnished a couple of days before the race, so we were going to do everything we could to repeat.”  

Caroline Grant Zarrella, who is married to Ron, won the Spirit of Tradition class in their Jim Taylor-designed, 50-foot Blackfish. Jeff Tucker, sailing the Alerion Physalia, finished second, just 21 ­seconds behind Sea Horse.  

One of the fun things about a pursuit start is seeing different boats under sail as you pass or get passed. Of course, no one likes to be passed, but the camaraderie among the competitors was heartwarming. I think every sailor was just happy to be there. On the way out to the starting line, the crew of Blackfish gave the crew of the 1930 Olin Stephens design Dorade a spontaneous three cheers for no other reason than anticipating a great day on the water.

For many years, the Opera House Cup organizers struggled to create their own handicap rating rule. Help came along in 2015, when a group of classic-yacht owners formed the Classic Yacht Owners Association to promote classic-yacht racing. An important part of the mission was to adopt a suitable handicap rating rule so that boats from vastly different vintages and designs could compete fairly. Naval architect Jim Taylor heads the Classic Rating Formula committee made up of nine sailors with technical backgrounds. They work to establish consistent rules and ratings that are updated annually. The goal is to have a system based on seconds per mile.

The CYOA coordinates race schedules and regatta promotions in Maine, Rhode Island, Connecticut, Massachusetts and New York. More than 225 boats are registered on the CYOA website. The Opera House Cup is one of 14 classic-­yacht regattas sanctioned by the organization, whose board of directors includes representatives from the regatta organizing committees. The mission is “to promote regional cooperation by sailors who are dedicated to owning, maintaining and racing sailing vessels.”

With the Opera House Cup, the regatta is open to boats with wood or wood-based cold-molded hulls and a minimum overall length of 24 feet. Trophies are presented to overall fleet and individual class winners. Author and previous Opera House Cup winner (2006) Nat Philbrick says that the Opera House Cup is a little like the Macy’s Thanksgiving Day Parade: “It is really one of those events that is as much an aesthetic thing as it is a competitive event.” 

Opera House Regatta
Alerions, including Seahorse round the mark. Roger Vandenberg Photography

The Opera House Cup is one of several events during Nantucket Race Week in late August. Race week is hosted by Nantucket Community Sailing, which gets more than 1,000 young people on the water for instruction and recreation every year. Executive director Diana Brown says, “Thanks to contributions and support we receive from Opera House and race-week competitors, about 25 percent of our budget is covered for the year.”

Nantucket is one of the finest places in the world to sail. On most summer days, a reliable breeze fills in across Nantucket Sound. At a time when foiling boats have taken over the America’s Cup, and foils are on five of the 10 classes in the Olympic Games, it is refreshing to see classic yachts racing and cruising in such a great place, giving sailors the joy of being on the water.