Skip to main content

Dawn Riley: A Life of Sailing

It’s 0900 on the dot, and Dawn Riley is starting the morning meeting. With military precision, she scrolls down an agenda she’s been working on for the past three hours. How’s that fiberglass repair? What’s up with the shipment of boats to Abu Dhabi? She scribbles a diagram on a whiteboard denoting proper anchoring technique.

It’s 0900 on the dot, and Dawn Riley is starting the morning meeting. With military precision, she scrolls down an agenda she’s been working on for the past three hours. How’s that fiberglass repair? What’s up with the shipment of boats to Abu Dhabi? She scribbles a diagram on a whiteboard denoting proper anchoring technique. At 0915, a young woman shuffles in, apologizes for her tardiness and mumbles something about the traffic. Dawn shoots back, “Well, you should have left earlier.” Then she asks everyone to say what they did the day before and what they are planning to accomplish today. She does not waste a minute. The meeting ends as abruptly as it began.

It’s a meeting Dawn has conducted a thousand times before, with teams racing in one-design fleets, the Whitbread Round the World Race and the America’s Cup; teams located in San Diego, New Zealand, France, Spain; teams that include the likes of Buddy Melges and Dave Dellenbaugh. Today she’s leading a team of 10 salty sailor-types, all clad in work clothes, all employees at the Oakcliff Sailing Center on Long Island, New York, which has been training serious sailors since Dawn dreamed it up in 2009.

Allegedly, Dawn is 50 years old, but you’d never guess it by looking at her. Five and a half feet tall, she wears her blonde hair long and natural, without a trace of makeup on her tanned face. She has a pair of swimmer’s shoulders and toned legs that could only be attached to someone who has worked out six days a week for the past 35 years. She’s tough, opinionated and, in her own words, intimidating. “People think I’m scary,” she says. “But sometimes it’s just more efficient to be scary.” She conducts herself with the confidence of a sailor who has “been there, done that” because, well, she has.

You might have first heard about Dawn Riley in 1989, when she sailed on Maiden with the first all-women team in the Whitbread Round the World Race, or in 1992, when she became the first woman to play an active role on an America’s Cup team, America3. Maybe she crossed your radar in 1993 when she took over as skipper for the all-women Heineken team following a mutiny partway through the race, or in 1995 when she captained the first all-women’s America’s Cup team. Then again, maybe it was in 2000 when she was CEO of the America’s Cup team, America True, or in 2007 when she was general manager of the French Cup team, Areva Challenge. She is the first American, male or female, to sail in three America’s Cups and two Whitbreads. She was the first woman and youngest person ever to manage an America’s Cup team. Her list of sailing accomplishments is only eclipsed by the trail she blazed to create it.

This One’s for the Girls

It’s the last night of Wednesday night racing at Oakcliff Sailing Center, and 19 sailors are signed up to race in Match 40s. As competitors trickle in, director of training Liz Shaw assigns them to boats and says, “Hope, you’re skippering the all-ladies’ boat.”

“WOMEN!” Dawn yells from across the room, fingers typing like mad on her laptop, a Bluetooth secured in her right ear. I’m shocked to realize she isn’t just double, but triple tasking. Who knew she was even paying attention?

“What’s wrong with calling them ‘ladies’?” laughs Ladi Oguntoyinbo, a 30-something man who’s been with Oakcliff from the start.

“It would be like me calling you ‘boy,’” explains Dawn.

“Huh, right. I guess you have a point,” says Ladi.

Soon afterward, the teams head to the water, only to find the breeze has completely died. “No sailing tonight,” however, is not a part of Dawn’s vocabulary. “We’re going to do dry-run spinnaker practice on the mooring!” she announces. “This is something we used to do in America’s Cup training.”

Before long the teams are all receiving lessons in setting, gybing and dousing their kites as Liz and Dawn zoom around coaching in RIBs. At one point, Dawn tells a young team: “If you’re ever trying to sail a spinnaker in super-light winds, like say on a Bermuda Race, you can actually optimize it by gathering the clew in your arms and minimizing the amount of kite that’s trying to fill.”

Be it the America’s Cup or the Bermuda Race, Dawn’s coaching is constantly peppered with references to a lifetime of sailing experience.

As we drive the RIB back to the docks, I ask Dawn if her earlier reaction to the “ladies” comment might have been a little defensive. But she explains: “The minute you start accepting prejudice as ‘just the way people talk’ is the minute you start to be defeated. On the other hand, if you decide you’re going to change the way people talk, you have a responsibility to move the conversation forward. And you can never let down.”

She also tells me a little about what it was like being a grand-prix racer back when it was a field open only to men. During her 2000 America’s Cup campaign for the America True team, for example, Dawn says: “We would have a potential sponsor dinner, and I would find the waiter and tell him or her specifically to bring me the bill because I wanted to pick up dinner. Many times, he or she would still bring the bill to the most senior-looking man at the table. I would take it, sign it, and not leave a tip. Maybe that was a little cruel, but if you don’t stand up to what’s wrong, no one will change it.”

Years before, she was signed up to race at Miami SORC. Because crew organization was completed over the phone, the boat’s owner thought it was “Don” sailing with him instead of “Dawn.” Upon seeing Dawn, he promptly kicked her off the team and said, “I don’t need to have any goddamn c***s on my boat if I don’t want to.” Dawn’s reaction? “He was right. He didn’t have to. So I got on another boat, in a different class, and we won.”

In the 20 years since Dawn started racing, she says there has been a quantum shift in the way women are viewed both in sailing and in business. In her book Taking the Helm, which tells the story of racing Heineken in the 1989-90 Whitbread, Dawn writes about practices in which the team’s boyfriends would come on board, and Dawn would have to kick them off so they would stop taking over for the women. Today, she says, when she creates teams of young sailors at Oakcliff, “I swear they don’t even see gender.”

Of young women pursuing professional sailing, she says, “They’re part of a generation that is starting to get it. They know they’re strong, and they’re good, but they also have respect for those who came before them. There were some ridiculous times, but thank God I’m a person who can fight,” she says. As she does so, I swear I see her tear up. But we have no time for mushy stuff. It’s off to the next event.

Saving Sailing

Dawn Riley can change from sailing clothes to formal attire faster than any woman I’ve ever known. You wouldn’t guess it from her tomboy tendencies, but Dawn has a few closets full of red-carpet dresses, most of which she’s acquired for galas for the Women’s Sailing Foundation, of which she is a former president. She goes from sporty to sultry in under five minutes, although even in a gown and heels her well-defined muscles give her away as a jock. This evening she throws off her Oakcliff uniform, throws on a dress, and we’re off to a fundraiser for Oyster Bay Main Street, an organization dedicated to preserving downtown Oyster Bay, where Oakcliff Sailing Center makes its home.

After a round of drinks, a speaker takes the microphone and gives Oakcliff a significant nod for what it’s brought to the town: the business (45 full-time summer residents, plus 1,000 transient racing sailors) and the energy. Afterward, a father of an Oakcliff trainee raves to me about Dawn and how much she’s done for sailing. Another friend tells me emphatically, “She’s amazing! I go by that place and find Dawn doing everything! She paints, she fixes boats, she teaches sailing—she even does the laundry!”

So how does a Cup veteran from Detroit, Michigan, end up in Oyster Bay, Long Island? Following the 2007 America’s Cup, Dawn decided her next move would be to run the America’s Cup, run the Volvo Ocean Race (successor to the Whitbread), or run for office in Michigan. Then she received a call from Hunt Lawrence, a successful businessman with a peculiar problem: he had too many sailboats and didn’t know what to do with them. He hired Dawn as a consultant, and in a matter of months she had combined her decades of sailing experience to create the Oakcliff Sailing Center, a training center for adult sailors seeking to improve their skills. The idea was to have a facility that taught competitive sailing as a whole—the racing, the fitness, the boat and systems maintenance, the fundraising and the business. She wanted serious sailors to come for months at a time, live and breathe sailing on a variety of boats, and eventually start careers as pro sailors or in the sailing industry. She wanted to build future Olympic, America’s Cup and Volvo sailors and generally “up” the U.S.’s place in global competition.

Not only did Hunt and his son, Bryan, love the idea—they loved Dawn too, and they asked her to move to Long Island to launch it. Within a month, she’d packed up her life in Michigan and was on her way. “I came out here with a three-year vision to get it up and running and then hand it off to someone else,” says Dawn, “but it kept growing and becoming what it is today,” which is a living, breathing, incubator for the future of the sport as a whole.

This year, Oakcliff hosted 26 events, including the U.S. Women’s Match Racing Championship, the ICSA Sloop Nationals, and the Nacra, 49er and 49erFX Nationals. It also hosted 13 full-time trainees, or “Saplings” for four to five months, each with unique goals. One former Sapling, Liz, told me about her summer: “One day we’d be racing against Rambler; the next day we were learning how to scrub the bilge. Another day [Puma racing veteran] Kimo Worthington walked in the door. [Multihull champion] John Casey coached us on the Nacras. Olympic sailor Kristen Lane trained with us, and lived with us in the bunkrooms. Everything about the program was so relevant, so now.”

Since Dawn helped open Oakcliff in 2010, the fleet has expanded to include Melges 24s, Farr 40s, offshore racing boats, Olsen 30s, Match 40s and the world’s largest collection of Olympic class Nacra 17s, 49ers and 49er FXs. Next year, they’re thinking of adding two 30-foot foiling cats. Oakcliff is an official training center of US Sailing Team Sperry Top-Sider, and it regularly competes and places in grand-prix events worldwide. Alumni include Volvo Ocean Race sailors Mark Towill and Charlie Enright.

Clearly, Oakcliff is actively achieving its mission of “raising the level of sailors and sailing in the United States.” And Dawn is actively at the helm.

Something’s Gotta Give

Thirteen hours after our day began, Dawn and I are driving home, and I’m pretty exhausted.

“Dawn,” I ask, “do you even take vacation?”

She laughs. “I’m too busy to have a life! When everyone is working normal hours, things are falling through cracks, so I use my holiday breaks to get caught up.”

“Well, do you ever take breaks?”

“I kind of suck at that,” she says candidly. “But if you’re going to be successful, you have to always be working on the next project, so there’s very little time to enjoy the one you’re in. I do try and take a moment here and there to reflect. Like for instance, last week a local yacht club sunk two of our boats, and I went out there to re-float them. It was in the 50s, and we were in and out of the water, soaking wet. At 11 o’clock at night I jumped down below to see if the sails were on board, and when I stepped on the sails, the entire cabin lit up with bioluminescence. It was so cool! Those are moments I stop for.”

As it turns out, bioluminescence on a half-sunken boat doesn’t actually count as a “break” for the human body, and this past year, after decades of pushing, Dawn’s body started to push back. Following a month of flu-like symptoms, Dawn ended up in the hospital with a diagnosis of diverticulitis, an intestinal condition that occurs when the lining of the colon becomes inflamed. Often stress-related, it can result in an extremely painful perforated intestinal track, which is what happened to Dawn.

During the next 10 months she was in the hospital five times and had 18 inches of her colon removed. Throughout this period, she followed the recovery protocol precisely and, once she was feeling better, allowed herself to start working out again, a decision that led to a whole new disease: rhabdomyolysis, or swelling of the muscle that, if left untreated, can cause kidney failure. Back to the hospital.

“Oakcliff nearly killed me,” says Dawn. “I think it was a wake-up call for everyone.”

At the next morning’s meeting, someone requests a new scissors sharpener for the sail sewing machines. Someone else asks about “adult supervision” during the upcoming ICSA sloop championships, to which Dawn replies, “When I was racing in college, we didn’t have coaches or adult supervision. But I do remember once being in the trunk of a car with a keg…”

She addresses every question with precision, flies through her inbox, which she keeps below 300, and ends the meeting with: “Before the Acorns arrive for training next summer, I want to make a list of things they must be able to do, including tie a bowline and do 25 pushups in under a minute.”

Save for her recent year of poor health, Dawn has never not been fit. When she was working out with the 1992 America’s Cup team, her upper body was stronger than some of her male teammates. Though she’s experienced many decades of “the latest fitness rage,” she now works out five to six times a week, doing sailing-specific cross-training. She tells a great story about a black-tie fundraiser for the Women’s Sports Foundation a few years back, where Lila Ali (pro boxer and daughter of Mohammed Ali) announced that her table would donate $10,000 if a woman could come on stage and do 25 push-ups. Dawn jumped up, sprinted to the front and busted out 25 pushups, all in a gown and heels. Since then, the challenge has become a tradition.

You have to wonder: is someone like Dawn born this way? How does a person become so fierce, so focused and so enthralled by sailing? Dawn didn’t grow up racing, but she did sail with her family on their 36-foot wooden boat. Her mom was a sailor, as was her father, his mother, and her father before that. Dawn’s parents met on a boat at a regatta. The family spent every summer sailing together, and when she was 13 they cruised from their home port in Detroit, through the Great Lakes, up to Maine, down the East Coast, through the Caribbean, to Grenada and back. In Taking the Helm she recalls long nights on watch with her sister Dana, enveloped in a spectacular starry sky. She writes: “When I was growing up, my parents were strict about things like doing the dishes and saying please and thank you. But when it came to adventure, the idea of fear was never introduced.”

That cruise gave her a sense of ownership and taught her to respect equipment. “It was a 36-foot wooden boat, and there were five of us. You had to stand watch. You had to roll up your sleeping bag and put it away every day. It didn’t matter if you were four years old.” To this day, she expects that level of discipline from everyone who walks through the door at Oakcliff. She’s been known to conduct random room-checks for tidiness in the bunkhouses, even when Olympic athletes are in town.

By age 15 Dawn had her first summer job captaining a boat, as well as her first experience telling her father what to do on said boat. That power struggle ebbed and flowed over the years and was compounded when her parents divorced, although both mom and dad stayed involved in Dawn’s sailing. Her mother was an enthusiastic fan—in the front row at Whitbread stopovers—and her father served as development director of America True, a 501c3 entity that Dawn helped found in 1997 when she was campaigning for the 2000 Cup. The organization still introduces sailing to young people across the nation.

In college, she picked up dinghy sailing, joined the team at Michigan State, and was team captain by senior year. While others were studying biochemistry, Dawn was researching how to apply for grants, which she used to purchase 10 new suits of sails. She then bargained with the local Hood sail loft to let the team help sew the sails in order to save money. Even then she was an innovative fundraiser.

In the years between college and Maiden, she worked on boats around the world and established a home base in Florida. Then, as Maiden became America3 became Heineken became America True, Dawn’s roots spread around the globe. At one point she fell in love with both New Zealand and a Kiwi who was also a career sailor. Though the two were engaged for a number of years and owned a house together in New Zealand, he eventually decided against marrying a sailor. Interestingly, in all of her stories, including the Whitbread Race in which her broken boat finished last, Dawn claims her only actual “failures” have been in her personal relationships.

Up on the Roof

Over the past few years, Dawn has cleared out her storage units in New Zealand, San Francisco and Europe. She still owns a house in Detroit, a condo in Annapolis and a Passport 40 on San Francisco Bay (which, by the way, is for sale). She also rents a charming one-bedroom apartment in Huntington, New York, which is decorated simply with remnants of her past: a painting by her best friend and college sailing partner, Renee, a winch-style pepper grinder from a Pro-Am Regatta. The outside patio, as large as the apartment itself, is bordered by potted plants—herbs and vegetables that Dawn uses to cook, when she has time to entertain.

She strolls around the perimeter of the roof, touches the basil, checks on the zucchini and talks broadly about her next five years. In the wake of her recent medical scares, Dawn is hoping to take a slightly different tack. She wants become a full-time fundraiser who sometimes coaches for Oakcliff and explains, “There was so much pressure in the beginning. Now it’s big enough and strong enough to go forward without me.”

So what’s the lesson in all this, Dawn Riley? By now I know there’s no question she doesn’t have an answer for, so I wager. She thinks only briefly and replies, “I don’t believe there is a strategy for living life. I think you just have to try to stay focused on doing the right thing. That’s all you can do. And if you’re always doing the right thing, you’ll be fine.”



What's it Like to Sail a Legend?

At 110 years old, the storied pilot cutter Jolie Brise powers off the wind. In 1851, the New York pilot schooner America sailed to England, beat the Brits at their own prestigious yacht race (which came to be known as the America’s Cup), and launched an evolution of the East more

Alexforbes Archangel1-1 (14)

Cape2Rio Draws to a Close

With just four boats still on their way, it has been a long road to Rio for the fleet competing in this year’s Cape2Rio. Larry Folsom’s American-flagged Balance 526 Nohri took line honors and a win in the MORCA fleet, finishing with a corrected time of 18 days, 20 hours, and 42 more


Close Encounters: A Star to Steer By

I first met Steve and Irene Macek in the proper way—in an anchorage full of bluewater cruising boats. This was in St. Georges, Bermuda, in the spring of 2019. Theirs, without doubt, was the most distinctive boat there—an immaculate, three-masted, double-ended Marco Polo schooner more


The Ocean Race Leg 2 Kicks Off

After a trial by fire start to the race and only a brief stop for limited fixes, the five IMOCA 60 crews in The Ocean Race set off for Cape Town, South Africa, early on January 25. Despite arriving somewhat battered in Cabo Verde, an African island nation west of Senegal, the more


Cruising: Smitten with a Wooden Boat

I was sailing down the inner channel of Marina del Rey under a beautiful red sunset when Nills, one of the crew members on my boat, pointed out an unusual and unique-looking 40-foot gaff-rigged wooden cutter tied to the end of a dock. Its classic appearance was a stark contrast more


Racing Recap: Leg One of The Ocean Race

New to spectating The Ocean Race? Managing Editor Lydia Mullan breaks down everything you need to know to get started. more


From the Editor: Keeping the Hands in Hands-On

SAIL Editor-in-Chief Wendy Mitman Clarke enjoys a sunny autumn cruise in her Peterson 34 on the Chesapeake Bay. It was late afternoon just after the U.S. Sailboat Show in Annapolis when I climbed aboard the last boat on the schedule. I and others who review and sail boats for more


B&G Announces New Zeus S Chartplotter

B&G has long been putting out top-of-the-line electronics, but the new Zeus S Chartplotter is a new take on the best way to give sailors the exact information they need, when they need it. “So many more people sail shorthanded these days, whether as a couple or when they’re more