In the tailwind of tropical storm Dorian, a strong and consistent breeze propelled sailors through the 42nd annual Moffett Race on Sunday.

Alan Wilson won the race aboard his 28-foot Stuart Knockabout, Altius. This is Mr. Wilson’s third time winning the race, each time with a different boat of unique design.

It is an impressive feat to win the rugged 15-mile course once. A 15-second handicap placed on boats that have won in the recent past makes it even more difficult to repeat. There are only two other sailors who have won the Moffett more than once, but no one else has won the race in a different boat, let alone two different boats.

“Well, I guess you might say it was luck,” Mr. Wilson said following the race. “Every different type of sailboat has a perfect wind speed and condition to trim the sail just right. Part of finding the sweet spot is knowing what boat sails best in what conditions, and Sunday was a perfect day for a Stuart Knockabout.”

Roger Becker, master-handicapper of the Holmes Hole Sailing Association, the organization that hosted the Moffett Race, confirmed Mr. Wilson’s claim.

Tango and Apres navigate the course. — Louisa Gould

“Everybody had a fair tide up the sounds to Makonikey. But because there was an ebbing current going towards Gay Head, those who were there early were turned into the foul-current and had to run downwind against it,” Mr. Becker said. “The slower boats that didn’t get down until an hour later had a fair tide coming back, which made the race more favorable for the smaller boats in the end.”

Mr. Becker continued: “What makes this race unique is that no matter what kind of boats show up, there is only one prize. So all monohull boats, from 18 to 70 feet, race as if there is only one class.”

The first time Mr. Wilson won the race was in 1993 on his 27-foot Soling. The Olympic-class boat was also named Altius. His second win in 2001 was aboard his boat Chantey. The stout, 38-foot wooden boat weighed over 37,000 pound and was originally built in 1927. Mr. Wilson has since sold Chantey to join the classic fleet of wooden ships owned by Capt. Bob Douglas.

Mr. Wilson’s new Altius is similar in size to the first Altius, but much different in design with her moderate rig, light helm, open cockpit and long sweeping hull.

But the history behind it is what makes the boat special,” Mr. Wilson said “The original boat was designed by L. Francis Herreshoff in 1932. . . She lived in Maine for 40 years in obscurity until she was discovered by a company out of Mattapoisett, who reproduced her in fiberglass.”

Mr. Wilson has sailed his new Altius in the Moffett Race the last five years, placing as high as third. This was the year, he said, that he finally feels like he has found the “sweet spot” of his new vessel.

“I’m a knucklehead to have gone through so many boats. Some people take a lifetime to learn the qualities of just one. But I love messing around with different boats. It kind of feels like getting to know a new friend.”

At the awards ceremony following the race, many sailors were curious if Mr. Wilson would try to win his fourth Moffett Race in a fourth boat.

Mr. Wilson said he has no such plans. “I’m 66,” he said. “I think I have the boat that I will sail the rest of my life. It’s a perfect boat for me.”

“But then again. If something comes along that’s even more perfect, I guess we’ll have to see.”