It has been nearly two decades since a year-round Nantucket resident won the Opera House Cup Regatta. Chris Magee, owner of the Zingara, was the last year-round winner back in 2005. Bill Liddle—with his 26-foot Alerion, Fortuna—hopes to break that two-decade drought after a third-place finish in 2023 has him heading into 2024 with plenty of momentum. “To win the Opera House Cup I would be ecstatic given the people I am racing against,” Liddle said. “I’m mostly familiar with the Alerion sailors, all of whom are really competent and highly skilled individuals who have been doing it for a while. To be able to actually beat all of them would be pretty fantastic.” Liddle moved to Nantucket as a teenager in the late 1970s and was quickly introduced to sailing by family friends Vladdy Kagan and Erica Wilson. They were passionate sailors, and it didn’t take long for that passion to rub off on Liddle. He said the idea of getting on a boat gives him the ultimate sense of freedom.

“I remember sailing up the harbor. There used to be a barge up there, and I just remember going up to it, tying up and hanging out there and throwing shells in the water,” Liddle said. “That was a strong memory. I suppose I have many memories exploring Polpis Harbor on a calm day. It’s pretty unique. The world slows down when you’re on a boat.”

Sailing continues to be an escape for Liddle. He recently took time away from his work to sail with Alfie Sanford from the Azores to Bermuda. He has also sailed in the Caribbean to partake in some clinic work and competed in regattas in St. Petersburg, Florida, this past winter.

“I would sail just about anywhere if given the opportunity, but I will say that Nantucket for day sailing is still the best,” Liddle said. “There is no doubt. But sailing with Alfie from the Azores to Bermuda was an extraordinarily memorable time with him just as a teacher, but also looking at stars in the middle of the night in the middle of the Atlantic. Then when it was calm the next day, being able to swim in the ocean while seeing an outback whale breaching in front of you.”

Liddle’s love of being on the water has never waned. Windsurfing became his main hobby after graduating high school and helped him discover his love for speed on the water. Liddle knew that one day he would return to his sailing roots, and this hobby helped him come to the realization he wanted to do more than sit back and relax on his boat while exploring the picturesque island when that day came.

Liddle has been selling real estate on the island since 1992, and after a brief two-year sabbatical from 2000 to 2002 to work in New York City as a real estate project manager, he returned to the island and co-founded Great Point Properties alongside Greg McKechnie, where he remains to this day.

As his career and family began to shape into form, he found himself desiring to get back out onto the water to sail. It led to him purchasing a 38-foot Alerion Express Fiberglass boat with a modern design and small living area below.

“I quickly learned that my family didn’t really want to sail with me,” Liddle joked. “They had no interest and just didn’t embrace it the way I thought they would. So I then started racing the boat and we would do these handicap races out of Nantucket Sound. I quickly realized that all of the other boats were much more serious sailors and much more serious boats. I decided that if I want to race, I should get into the one-design fleet where there are other boats within the same ZIP code as me.”

It led to Liddle giving Alfie Sanford a phone call in 2016, over 40 years after Liddle had first expressed his interest in an Alerion boat to Sanford.

“Fortuna is an Alerion, and Alfie and Edward Sanford reintroduced the class in the 1970s to Nantucket because they were building them,” Liddle said. “It was the reintroduction of a boat that was designed around 1914. In 1980, when I was around 14 years old, I wrote Alfie a letter asking for a brochure. He lived right around the corner and sent me a brochure. Then in 2016, I called him and said I’d love for him to build me a boat. He’s like, ‘You might have taken longer than any other client I've ever had.’”

He will be putting aside the leisurely approach and replacing it with a more business-like mindset, with two experienced sailors by his side, including a young local sailor named Sam Turner, who has been on the Nantucket Yacht Club sailing teams in the past.

The boat’s construction began in Chatham in 2017. The Pease Brothers began building it before being sold to First Light Boatworks, who completed the work under Woody Metzger.

“The boat is made out of cedar and teak wood,” Liddle said. “It’s what’s referred to as a cold-mold construction, where they layer laminates of wood over a shell or form of the shape of the hull, and then they put laminates of wood on and follow the form. It’s just one thin veneer after another and then it’s finished with mahogany and teak and other species of wood.”

Looking ahead to the 52nd Opera House Cup on August 18, Liddle will be taking a slightly different approach from years past where he has been accompanied by friends with little to no sailing experience. He will be putting aside the leisurely approach and replacing it with a more business-like mindset, with two experienced sailors by his side, including a young local sailor named Sam Turner, who has been on the Nantucket Yacht Club sailing teams in the past.

“He is a local kid but away at boarding school now,” Liddle said. “Then I have a friend named Andrew Kotchen, who is an architect out here and in New York looking for some peace of mind, so we are going to provide that in some way. Andrew has been a racer since he was a child.”

Liddle says that while he will be taking a more serious approach to this year’s regatta, his top priority remains having fun and appreciating all of the beautiful boats he hopes to see behind him.

“I always prioritize having fun, but look, if I feel like all of a sudden we have some competition being reeled in, my focus might change from fun to trying to place well and beat them out,” Liddle said. “But being out on that Alerion is just pure joy. It is a simple boat and absolutely elegant. I enjoy looking at every square inch of the boat, appreciate the design and love the smell of the wood. Being out and being able to see all of the beautiful boats around me as well as the natural beauty surrounding us is a wonderful escape and, on race day, is really quite meditative—especially if we can win. All the little worries in my head seem to go away and I am just fixated on what is in front of me.”

“It’s so invigorating to be surrounded by boats where some are new and just beautifully designed and beautifully engineered, while others are stunningly gorgeous and have history,” Liddle said. “It is a real joy. I am looking forward to it.”