Riding the rail of a classic sailboat while racing off Antigua’s southern coast, the scenery alone is enough to overwhelm the senses. The 20-knot trade winds, the rolling swells and the bright blue sky are pure magic. Add 41 classic yachts to that scene, and a sailor can feel as if he’s been transported to the 19th century.

The conditions and the extraordinary boats are why sailing enthusiasts have been coming to the Antigua Classic Yacht Regatta (ACYR) for 32 years. The event, which evolved out of Antigua Sailing Week to give classic-boat owners an opportunity to race against similar vessels, is considered one of the year’s premier regattas for classic yachts. It shares many elements with other classic sailboat races—camaraderie at the docks, a concours d’élégance and parties—but in the end, the ACYR is about the sailing and the yachts.

“We have it all: a welcoming island, perfect weather, competitive racecourses and stunningly beautiful yachts in pristine condition,” says Carlo Falcone, race chairman for the 2019 event, and owner/captain of the 80-foot Fife Mariella.

In Antigua, the word “classic” is loosely defined. Fiberglass boats, for instance, can participate in the Classic GRP class, while other non-wood vessels can enter the Spirit of Tradition class. “As long as the boats are beautiful,” one race committee member says.

There are ten classes to ensure everyone races competitively against like boats, according to Antigua Yacht Club Commodore Franklyn Brathwhite. “The emphasis is on fairness and fun,” he says. Boat sizes range broadly. This past spring, the Andre Hoek-designed Holland Jachtbouw Athos was the largest yacht at 203 feet, while the Carriacou-built sloop New Moon at 32 feet was the smallest. And while Athos had professional crew, local kids with the West Indies Sail Heritage Foundation sailed aboard New Moon. “Everyone here is on the same level, whether you come in flip-flops or a private jet,” says ACYR co-founder Kenny Coombs. “We are all here for the sailing.”

Queen of the Classics

This year, four boats with ties to New England turned heads at ACYR, and one of them took center stage: Arrluuk, a 58-foot Bounty model by L. Francis Herreshoff that Legendary Yachts built in 1997. She sailed under the New York Yacht Club burgee and snagged the Grande Dame trophy for best overall yacht in the concours d’élégance.

The yacht, whose homeport is Jamestown, Rhode Island, is the Caribbean liveaboard home of owners Steve and Tricia Frary and their two children, 13-year-old Elizabeth and 11-year-old Nathaniel. The Frarys raised the kids on a succession of Herreshoffs. They started with a Herreshoff 12½, moved up to an L. Francis Herreshoff Stuart Knockabout, and then cruised a 1951 42-foot Sidney Herreshoff ketch in New England before buying Arrluuk.

Arrluuk gave the Frary family the interior space they needed for extended cruising, with a split rig that let the family handle the sails and boat themselves. After a 2017 refit, they had Arrluuk shipped to Antigua. Within months, the family won two consecutive races in 20 knots of wind at the Carriacou Regatta Festival.

At the ACYR concours d’élégance judging, the Frarys knew they had serious competition. “We think the judges were very generous in considering that we were a family program that had been living on board for over a year.” Steve said.

But, Arrluuk wasn’t just a pretty face. Her name is Inuit for killer whale and she slayed the competition by winning all four of her class races at Antigua. The kids worked as staysail and jib sheet trimmers and handled the main runners. “They used the skills and knowledge they gained over the year of living on board,” Steve says. “They take pride that they are often the only kids who have significant responsibility in the race.”

With hurricane season on the way, the Frarys plan to make their way to Barbuda, St. Barts, St. Maarten and the British Virgin Islands. They hope to head to Panama at the end of 2019 and sail the Pacific in 2020. They’ve been wondering if a more modern boat might be better suited for the long passages of the Pacific, but having had so many rewarding experiences on Arrluuk, they know that leaving this yacht won’t be an easy decision.

“We planned a six-month itinerary,” Steve says, “but we are having such a great time that as a family we decided to extend it. For me, Tricia and the children, cruising the Caribbean has been the most amazing life experience.”

Northeast Pedigree

Blackfish, a 49-foot racer/cruiser sloop built in 2017, is a New England boat through and through. Carolyn Grant and Ronald Zarrella of Nantucket, Massachusetts, commissioned her from Maine’s Brooklin Boat Yard, and designer and naval architect Jim Taylor of Marblehead, Massachusetts, designed her.

Blackfish combines classic looks and modern touches. Her mast and boom are made of carbon-fiber but finished to look like wood, and below the waterline her underbody has deep, high-aspect-ratio appendages, including a fin keel with a bulb. With her cold-molded hull—a Brooklin Boat Yard specialty—and a minimalist interior that doesn’t even include a shower, she weighs in at a svelte 16,750 pounds.

“I tried to give her lively performance, handsome aesthetics, a comfortable cockpit and ample stability,” Taylor says. “I hope her long, graceful overhangs, sweeping sheerline and small counterstern are seductive, but the focus remains on contemporary performance.”

Inside, other than the electronics, Blackfish gives little hint of modernity. With a Herreshoff finish that includes a cabin sole made from a diseased English black oak and quarter-sawn oak for the furniture and trim, she could have been built in the 19th century.

Blackfish won the concours d’élégance Spirit of Tradition class and with her owners and designer on board, took second in her class on the racecourse. To celebrate Blackfish’s
performance, Brooklin Boat Yard owner Steve White threw an Antiguan-themed party for
clients and other attendees, including representatives from Maine-based yards Yachting Solutions and Lyman-Morse. The gathering was an important reminder of New England’s
substantial boatbuilding capabilities.

Mah Jong, a 52-foot Sparkman & Stephens yawl, was built at Cheoy Lee Shipyard in Hong Kong in 1957, but Gannon & Benjamin Marine Railway in Vineyard Haven, Massachusetts, completely rebuilt her. She was relaunched in 2017. The boat’s owner, Pat Ilderton of
Charleston, South Carolina, had commissioned the restoration and was pleased that his captain, Alex Goldhill, won the single-handed race. “My crew of family and friends sailed well and had fun,” says Ilderton, who plans to sail Mah Jong to Maine and Nova Scotia for the summer. “We loved the regatta.”

Eros, a 115-foot, 185-ton staysail schooner, offers charters in New England and the Caribbean as part of the Nicholson Yachts fleet. She was built by Brooke Marine Construction Co. in Lowestoft, England, in 1939, but now she spends the summers sailing out of Bristol, Rhode Island.

Originally built out of Burmese teak over a steel frame for an American businessman who was marrying a British lord’s daughter, the yacht was long owned by Greek shipping tycoon Stavros Niarchos. Subsequent owners gave her an 18-year restoration and relaunched her in 2010. Now, according to Cameron Riddell, one of her current owners, she is “in perfect condition.” While her museum-quality restoration included a complete overhaul of her hull, her original Burmese teak hull planks remain.

Eros also races at classics events in New England during the summer, but Riddell is an especially big fan of Antigua. “There’s a lot of camaraderie. You meet people on the other boats, you talk about the sailing on the docks,” he says. “It’s social. if you like classic boats and you like sailing, you’re going to really enjoy the whole scene. It’s a stunning place to be and there’s lots of wind. Antigua is definitely the granddaddy of them all.” 

This article originally appeared in the July 2019 issue.