Dawn Riley is one of the most successful racing sailors in the world. 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, she first campaigned with Bill Koch’s victorious defending syndicate America3, as the only female sailor, in 1992. In 1995, Koch sponsored Mighty Mary, where Riley was the team captain for the first all-female crew. In 2000, she was CEO and captain of America True, whose parent foundation is still dedicated to putting at-risk kids on the water, and she was general manager of K-Challenge in the 2007 America’s Cup.
Riley, originally from Detroit, is now the executive director of Oakcliff Sailing Center in Oyster Bay, New York. Oakcliff is a high-performance sailing facility, founded to bolster the sport in America and build leaders through sailing.
First memory of being on a boat: I don’t have a first memory on a boat because I’ve kind of always been on one. My family always cruised extensively — since I was a baby. The year I turned 13 my mom, dad, younger sister Dana, brother Todd sailed for a year from Michigan, through the Erie Barge Canal to New York, up to Maine and then down to Florida and the Bahamas, through the Caribbean to Grenada and back — on a wooden 36-foot sailboat! That set me up to understand the full scope of what was possible on a boat.
First boat you owned: I have only owned two boats in my life, a Fireball with a significant other and Wanderbird, a Passport 40. The first boat I raced on without a relative was an Etchells at age 13 and I quickly moved on to the hot boats of the 1970s, a C&C 35 and then a C&C 65 and a few Choates and Frers.
Your dream boat: I already own my dream boat, a Passport 40. Unfortunately (or fortunately) Oakcliff has over 100 boats, so I really don’t need her. She’s actively for sale.
Most rewarding professional experience: Probably America True from a high-profile perspective. This was my America’s Cup team for the 2000 Cup in New Zealand. I was the CEO and captain. After being the only woman on Bill Koch’s winning America3 in 1992 and the team captain of his women’s team in 1995, I was able to not only talk about but show that the best teams are coed or mixed: The spirit of the team, the efficiency of using every resource to the fullest and the results proved it. I literally put my money where my mouth was, putting half of the entry fee for the America’s Cup on my credit card. So worth it. This is closely followed by what Oakcliff is doing. It is rewarding and challenging, but we do keep adding and morphing, so it is not over yet, but man is it a place where we can change the world.
Scariest adventure aboard: I honestly have only been afraid once on a boat. That time is quite well documented and in my book, Taking The Helm. We had lost half of our rudder, had rounded Cape Horn and were beam-reaching in 50 to 60 knots of wind with 3 to 6 knots of current with us. The ultimate wind-against-tide situation with waves breaking over us at the level of the first spreader. Lots of injuries, and it wasn’t that I was afraid for me, but the weight of the responsibility sank in. I was 29 years old.
Most memorable experience aboard: The 2000 Louis Vuitton race in New Zealand against Japan. We started with two penalties in 20 knots with gusts over 30. We finished with two holes in the boat and no penalties and in front, and we solidified our spot moving into the semifinals of the 2000 America’s Cup. Talk about adrenaline!
Longest time you’ve spent aboard: 38 days in the 1989-90 Whitbread. This was the first leg from England to Punta del Este, Uruguay. When we finished, it was the first time I actually had sea legs and had trouble walking. It might have had something to do with the sponsor, Beefeater Gin, though. Looking back, it was long, but we could have just kept going. That race was the last that was truly an adventure. We had limited communications through SSB and a “kind of daily” weatherfax report when it was working. We sailed through a hurricane and didn’t know until a journalist asked us how it was. We were just out there making a boat go fast 24/7 and taking it as it came. Quite a pure existence.
Favorite destination so far: New Zealand is by far my favorite place on Earth. But as I get older it seems farther and farther away from family. So a close second is northern Michigan (yes, I like the Kid Rock song) and across Lake Huron to Georgian Bay. If I could, I’d summer in Michigan and winter in New Zealand. It is good to have dreams and goals.
Favorite nautical book: I think my favorite is Endurance about Ernest Shackleton’s voyage. It was especially impactful, as I read it while we were sailing the second Southern Ocean leg of the Whitbread. It was truly incredible to be reading about the primitive gear they had while I was freezing in modern gear.
Favorite nautical cause you support and why: Oakcliff is my life. I thought I was staying here for my normal three-year campaign and moving on, but I think I’ve found a home. We have been able to build a place that is helping people discover and develop their futures both inside and outside of sailing. We are open to sailors of all levels, ages 15 to 100, and the sailing world is taking notice. We had six boats entered in the Bermuda Race and host multiple high-performance nationals and more match racing than anywhere else in the country.
Favorite quote about the sea: Not about the sea, but I use it in coaching all of the time. “Whether you think you can or you think you can’t, you are right.” — Henry Ford (also from Detroit).
This article originally appeared in the November 2016 issue.