Dawn Riley, the first woman to compete in both the America’s Cup and the Whitbread Round the World Race, is this year’s recipient of Mystic Seaport’s America and the Sea Award. In 1989-90, Riley was the watch captain/engineer on Maiden, the first all-women team in the Whitbread Round the World Race (now the Volvo Ocean Race). In 1993-94 she returned to the Whitbread as the skipper of Heineken, leading the only all-women team in that race.
A four-time America’s Cup veteran, Riley first campaigned with Bill Koch’s victorious defending syndicate America3, as the only female sailor, in 1992. In 1995, she was team captain of America3-backed Mighty Mary, with the first all-female crew. In 2000, she was CEO and captain of the America True syndicate, and she was general manager of K-Challenge in the 2007 Cup.
Riley is the executive director of Oakcliff Sailing Center in Oyster Bay, New York, which trains sailors for the Olympics, America’s Cup and other high-level competitions.
This article originally appeared in the May 2018 issue.