Photo: Nantucket Community Sailing

The Northeast sailing season kicks off in about three months and the CYOA’s Classic Yacht Challenge Series (CYCS) will be here before you know it! To continue our regatta spotlight series, we’re heading to the Islands of Massachusetts, home to Nantucket’s Opera House Cup.

To tell us more about these exciting events, CYOA caught up Phil Smith of the Opera House Cup:

CYOA: What is the history and tradition behind this regatta, and how does it influence the experience for participants?

Phil Smith: The Opera House Cup (OHC) was founded in 1973 by a group of local Nantucket sailors at the Opera House Restaurant, where Gwen Gaillard, the owner of this wildly popular watering hole, was holding court. She had just lost her husband, and the sailors, a rag-tag group reportedly quite well served at that point, decided to have an informal race to cheer her up. They all had wooden boats which many were living on, and the condition of several of the boats was sketchy, and not exactly in “Bristol condition.” An old champagne bucket was declared the trophy on which the winner’s name would be inscribed. One of the participants at the table offered that his wife was good at math and she could handle the scoring. (This quaint feature of the race would drive future competitors crazy, and it is only in the last few years with the CRF ratings that grumbling about the OHC “black box” handicap system have subsided.) Nine boats were in the first race, and our 50th annual race was celebrated three years ago. The OHC race holds the honor of being the first all-wooden-hulled classic boat regatta on the East Coast, if not the U.S.

CYOA: What sets the fleet of classic yachts at your regatta apart from other similar events? Are there specific types of yachts or notable vessels that regularly participate?

PS: The Opera House Cup attracts some of the finest classic wooden sailboats in the country and consistently includes over 20 Vintage (designed before 1940) beauties, the largest concentration of that Division in all the CYOA regattas. Past participants include former America’s Cup winners (Intrepid, Weatherly, Columbia), well-known competitors (Ticonderoga, Wild Horses, Blackwatch, Dorade, Santana and Valiant) and other notable yachts including the Mystic Seaport schooner Brilliant, Gleam, Marilee, Spartan and the J Class yacht Ranger. On the smaller side, boats in the Wianno Senior class and the classic Herreshoff-designed and Nantucket-built Alerions challenge the big boys, with Alerions winning the cup on three occasions.

CYOA: What is special at your event to celebrate the classic yacht racing community during the event?

PS: Opera House Cup weekend begins with a Classic Yacht Exhibition along the docks of the Nantucket Boat Basin on Saturday evening. The boats invited to be in the exhibition represent about 15 of the most prominent and famous designers of the last 125 years. The public is invited to stroll the docks and go aboard the magnificent boats, where the owners can answer questions and share the boat’s history.

CYOA: What aspects of your regatta make it a must-attend event for sailors and enthusiasts—whether it’s the location, race format, social atmosphere, or something else?

PS: Based on popular demand, a few years ago the OHC was changed to a pursuit start, and two winners are declared – the boat that finishes first and the plank-on-frame boat that finishes first. In 2023 ONAWA won the trophy on both counts. In 2020 a 26 foot Alerion, Scheherazade, held off a blazing fast Outlier by 1 minute and 44 seconds to win the trophy. Boats that don’t meet the Opera House Cup qualifications such as having a wooden hull and white sails, may be invited to race in the Invitational Division if they are historic or otherwise add to the spectacle of the race. The Opera House Cup Regatta is the grand finale of Nantucket Race Week. Social events include an informal dinner on Saturday night at Nantucket Yacht Club with food trucks and an awards party Sunday after the race on Jetties Beach.

CYOA: How does your regatta engage the wider community, and are there unique activities or events that connect spectators and non-sailors with the world of classic yachts?

PS: Sunday morning starts with the Rainbow Parade of about 20 disorganized Beetle Cats clogging up the channel off the Brant Point lighthouse, and the Parade of Wooden Boats leaving the harbor as they head out to the starting line. There is always a large crowd on the beach at Brant Point (estimated to be over 1,500) to see the boats sailing by and in the last two years we have added an announcer with a sound system on the beach that provides a brief overview of each competitor. Every year a printed program is distributed on the beach with pictures and thumbnail sketches of the boats, adding to the public engagement. In addition to providing a spectacular day on the water, The Opera House Cup serves as the primary fundraiser for Nantucket Community Sailing, a non-profit program that teaches sailing to over 1,000 kids, approximately 50% who live year-round on the Island and benefit from a generous scholarship fund, so anyone who wants to learn to sail can, without financial concerns.