Dawn Riley

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Home / News & Notes

Beneath the Surface

July 14, 2016

Beneath the Surface is a documentary short, featuring Dawn Riley, Betsy Alison, and Amanda Callahan, is about the discrimination faced by women in the sport of sailing.

Taking the Helm Released in Paperback

October 8, 2013

Taking The Helm

Oyster Bay (N.Y.) October 8, 2013 — When it comes to breaking barriers in big-boat sailing, few women can be compared to Dawn Riley. She was the first woman to manage an America’s Cup campaign, and the first American, male or female, to sail in three America’s Cups and two Whitbread Round-the-World races. Today, she serves executive director of Oakcliff Sailing Center in Oyster Bay (N.Y.), a unique school that grooms the next generation of world-class sailors. But the bedrock of her leadership skills were developed during a round-the-world race that took place 20 years ago, in a grueling contest that for Riley was not unlike getting an MBA during a game of survival.

This month, Riley is reissuing the story of that seminal race with her book Taking the Helm, written with coauthor Cynthia Goss.  Her adventure memoir tells the tale of skippering the 60-foot Heineken in the Whitbread Round-the-World Race. The next running of this race, now called the Volvo Ocean Race, begins in Spain in October 2014.

“I am amazed at how relevant the lessons of Heineken still are,” said Riley. “That race taught me how to lead, how to trust my own decisions, and how to overcome challenges—many of which threatened our lives … I hope a new generation of readers will become armchair sailors with this book and, like me, experience a great adventure while getting a crash course in what it means to take a leadership role.”

Taking the Helm tells the story of Riley and her crew in the 1993-94 Whitbread Round-the-World Race. Riley was telephoned after the first leg of this ocean marathon, when the crew on the only all-female entry in the race was riven by dissent, financial problems and personal conflicts; only a new captain could save this team from mutiny and lead the women to a successful finish. Riley quickly packed up her life and flew to Uruguay. After four days of hasty boat preparation and group training, the women set sail from sunny Punta del Este, unprepared for the perils of the treacherous Southern Ocean. The crew not only braved near-hurricane-force winds, numbing temperatures and jagged icebergs in the face of physical injury, dwindling supplies, equipment failure and overall exhaustion; they also faced bitter dissent amongst their crew. In the end, these women traveled much farther than the race’s 32,000 miles: with each leg and each new test, they learned to rally under their captain’s leadership. In recounting how she took responsibility for the lives of eleven other women, Riley tells an extraordinary story of self-discovery within the gripping context of the world’s most demanding sailboat race.

Riley wrote Taking the Helm during a landmark era in women’s sailing. After competing with Heineken in the Whitbread, she relocated to San Diego to sail with America3, the first all-women’s America’s Cup team. In the 2000 America’s Cup, she used her leadership skills to launch and become CEO of the co-ed Cup team America True, which for Riley was the next evolution for women in sailing: the team set out to do something unique by finding the best sailor for each job onboard, whether male or female. Leading a team of talented sailors hungry to compete on the world stage who earned their spots by talent and not gender remains a highlight of her career. But as Riley surveys the state of women in sailing today, she sees some amazing achievements but also slow progress for truly integrating women into the sport.

“Women have done great things in sailing—and will continue to do great things,” says Riley. “But as with any disadvantaged group, realizing they are disadvantaged is the first step, and  then it’s like a jolt, a wake-up call, and you make huge progress and have some successes; but you can get complacent and assume, we are just going to keep moving forward. That does not always happen. It takes energy, and it takes young people who will put themselves out there and make a difference.”

At Oakcliff Sailing Center—located 30 miles from mid-town Manhattan in Oyster Bay, New York—Riley is busy grooming those sailors. Oakcliff is a high-level training center with a specialty of teaching 15- to 30-year-olds to become leaders in the sport (other adult programs are also available).

Riley is the mastermind of the Oakcliff program, and in 2009 was contacted by the Lawrence sailing family of Long Island, who had amassed a fleet of boats and shoreside facilities. They asked Riley to propose ways they could utilize those assets. One of her ideas was to create a top-level educational center that would train sailors not only on the water, but teach them the many skills needed to become a leader in the sport—such as an understanding of sponsorship and the business of racing, boat construction and technology, teamwork, and leadership and management skills. Riley’s education was more a trial by fire: with Oakcliff, America now has a center where students learn all the skills needed to take a leadership role in competitive sailing.

Taking the Helm (originally published by Little, Brown and Company) is available in paperback ($17.95) and e-book ($6.99) formats from Amazon.com. The book has been republished by DR Ventures.

Dawn Riley is a past president of the Women’s Sports Foundation and a sought-after motivational speaker. For more information, visit www.dawnriley.com. For more on Oakcliff Sailing Center, visit www.oakcliffsailing.org.

The 2014/15 Volvo Ocean Race starts in October 2014 from Alicante, Spain; the all-women’s Team SCA will be competing in the race.

Our Friend Bart

May 13, 2013

Last August a few friends and I were sitting around a bottle of Moet at the St.FYC talking about the state of the America’s Cup. I don’t have a dog (or cat) in this race so I have purposefully tried to stay quite in public but in private I voiced my opinion. Stating you are going after the Facebook, not the Flintstone generation was one of the worst marking moves ever. It alienated the base of fans and funders in one sound bite. The claims of less cost were outright lies and the concept of making super sized yachts to make sailing super exciting doesn’t make sense. The 45s and the 72s look just about the same when watching them on a television set. I was and am worried about the future of the America’s Cup, an event that has consumed much of my adult life and provided most of my friends and one that I cherish.

I obviously have opinions including that from a management perspective, there was no adult supervision. One person was given all the keys to the castle with little or no checks and balances. There are some amazing things going on, specifically with television. But with at least initially unlimited funds they were never forced to make hard and well fought out choices.

That reckless decision making was foreshadowed by my friend Craig Monk on that night last summer. He said, Dawnsie someone is going to die on these boats, someone is going to die. Katie and I looked at each other and at Percy and Bart and got chills.

When a member of management says – “this was never on our radar” I have to ask, why the hell not? Every sailor did and now our friend is gone and I can’t imagine the sadness of his true best friends who were there and could do nothing. My heart is broken on multiple levels and I’m having a hard time finding the silver lining.

A Window Seat Away from Oakcliff is St. Barth’s

April 3, 2013

If anyone has been checking in on this site regularly they will have noticed that I haven’t updated it very much.  This is because for the past 3 plus years I have been fully immersed in starting up Oakcliff Sailing in Oyster Bay New York.  This is a full time project and we are doing amazing things.  Everyone should sign up for the newsletter and read more at www.oakcliffsailing.org or you can click on the logo to the right.

Every once in a while I escape the day to day craziness of the fast growing non-profit that Oakcliff is and get to go sailing on my own.  This latest time was the St. Barth’s Bucket.  I sailed on a Perini Navi again and the owners of this boat were first timers and they were wonderful.   The rest of the story although was a story of team building.

Shortly after arriving, I met the Captain and we realized that we were short racing sailors, a minimim of 5 sailors short.  So for three days between arrival and practice we scrambled and trolled the docks.  Our local helmsperson Fritz Bus was able to find two friends, Garth from St. Maarten and Vincent from St. Barths. One of our Spanish crew found Diego off of a charter catamaran.  And Bif the first mate called in Aussie rock star Nicky Souter.  I was lucky enough to connect with German Wolf Dietz who I knew from Morning Glory Days as well as Valencia where he was leading the German America’s Cup team when I was in charge of the French.

Across the 10 hours of practice time we managed to pull together a pretty good, if short handed team to hoist the absolutely HUGE sails on this 50 meter yacht.  We got them up and down, worked on hand signals and leadership and systems and procedures.  Oh and we learned each other’s names.

Race Day One:  We led for over 2 hours and 23 minutes and then eventually in this pursuit style racing the rest of the boats started to catch up.  For a while it looked like we were being invaded as the 35 boats, all 100 feet and over were sailing sails spread, downwind coming for us.  We managed to hold on to 5th place. Smiles all around.

Race Day Two:  It poured with rain.  The winds picked up well into the 30s and we split the leech of our main and were forced to retire.  This is when the team really pulled together.  We worked from a little after noon until dark, in the pouring rain to remove the 1200lb mainsail from the boom, get the 50 foot battens out, pack up the sail, winch it into the tender, which didn’t quite sink but came close. Then it was all hands onto the make-shift North Sail Loft to push and pull and roll and muscle the sail under the huge sewing machine, then flake and pack and load and winch it back up onto the deck.  This was all done in the pouring rain.  It was COLD and we worked until we couldn’t see anymore.  And we were truly becoming a team – the race crew, the permenant crew and the owners – together.

Race Day Three:  Up and at it by 6am and we managed to get battens in, tensioned, onto the boom, rolled onto the mandrel and then hoisted and lowered and only pulled out of the pre-feeder once and we were ready for the start!  The chef made sausage and bacon and some kind of a stick food and eggs and coffee so everyone was able to get nourishment before we headed around the Island.

The start was magic.  We got a good line sight, after three days of sailing this huge but slow accelerating and fast decelerating yacht we had a better idea of what 4 minutes on the water looked like.  It was a downwind start with about 25 knots of wind and we were pushing it very close. At 40 seconds we hoisted the spinnaker and kept the sock down.  At 30 seconds we were early and turned the ship towards the pin which was further downwind. At 20 seconds Fritz on the helm wanted to come up and I held him down.  At 10 seconds we yelled ‘Bucket Up’ and the spinnaker began to be unveiled.  We collectively held our breath and as the gun went off we were less than 3 feet from the line with the spinnaker up and a huge exhale and cheer went up.    The rest of the race had excitement.  A blown spinnaker sheet had all leap into action but the team handled it like they had been working together for months not days.  Even the guest and owners were in the mix running the 30 meters forward and pulling the sail in.  We finished mid-fleet but considered it a success.

As I mentioned to the owners, to me you win sailboat races and you loose sailboat races but what really matters is that you always work hard, through the finish line and improve as a team.  That is the magic of sailboat racing to me no matter if it is on a Match 40 or a gorgeous Perini Navi.

A Different Bucket

March 29, 2012

St. Barth’s felt very familiar this year and yet it turned out to be a whole new experience.  This was my third Bucket Regatta with the Perni Navi family and probably the 10th time I have sailed into the Port of Gustavia.

On Monday, we joined the boat in St. Martin and had a bit of work to get done, plus the passage over to St. Barth’s arriving well after dark.  A quick bite in town and up to the Auberge to assign rooms and cots and make sure that everyone had a place to sleep and we hit the hay.

Headed to St. Barths

The Wednesday before I found out that Hank Halstead or normal helm and one of the founders of the Bucket was too ill to make the trip.  On Thursday the Captain was fired.  On Friday the fired Captain got married so it took me until Saturday to find out that the four other racers he had organized would not be joining us. In a bit of a panic, I managed to convince Meg Gaillard–Myles to join us.  She had to bring her daughter Kate and their nanny Kendra.  Thus the shuffle to make sure that everyone had a bed!  I posted on Facebook: New team – fingers crossed!

The next morning I woke BRIGHT and early and feeling great as I headed down the road and up and down the mountains on a 55 minute hike to the end of the island and back.

Hill Houses

 

Last year this was a quiet hike. This year there were construction workers every hundred yards or so as they were repairing the walls along the road.  The craftsmanship was impressive as they were 3 or 4 artisans working in the quarry by the side of the road, hand chiseling local stone.  A pretty hard job but in a beautiful setting and these guys have skills!

Handmade Stone Walls

Now they probably weren’t that used to seeing a woman in black shorts and a hot pink jog bra walking, at pace, past their job sites.  But I am positive that they weren’t used to seeing what they saw on the second day.  I was inspired by all of the rocks around and choose two similar ones and proceeded to do 10 reps each of, bicep curls, triceps extensions, military presses, and a full set of shoulder sets continuously through the hike.

Road to the Tip of the Island

The first rock day, they kind of looked at me sideways.  The second a few giggled and commented “Elle est forte!”, after that they just started offering me bigger rocks to carry :-).

Tuesday was a scheduled practice day but it turned more into a boat-work day as three of our people had missed their connections and there was a fair amount to do.  Wednesday was finally  had a real practice day and we learned each other’s names as we pulled together a training session.

Thursday the owners arrived so the permanent crew was fully in owner prep and the race crew helped with a few odd jobs and then got out of the way.  This was the first time we had three women on board and I decided that in honor of that, instead of going to the most beautiful and natural beach, Saline Beach that we should find one where there were men in tight or no shirts who would serve us drinks.   We ended up at Nikki Beach.

It turns out that when I was rubbing the belly of the genie and making my wish I wasn’t quite specific enough.  Turns out that there was a cruise ship in town with 2000 men!  All men! Doh

Boys All Around and Not a One to Touch
The Mojitos Were Good!

Meg’s husband Rob arrived to race with another boat and when he joined us  their daughter Kate ran up to him to tell him about this great place where you can get drinks and then dance on the table.  Double Doh!  🙂

Finally it was race day.   Friday started out sunny and then went downhill from there.  The rain started – torrential rain! – and it was cold.  I shivered around the race course and the boat started to show some strain as well.  Something shorted out in the electronics and on one reaching leg the on-deck crew pointed out that our boarding ladder had deployed and it was stuck!

No Virginia this is Not Fast

Not a normal racing situation.  We managed to fix it within about 15 minutes and had 5 minutes to spare before we hoisted the kite.  We finished 4th and decided that the next day was going to be better.

Saturday was sunnier and we set off on the wiggly course.  In a ‘normal’ racing boat it would have been a fun little 19-mile jaunt up and down and between the islands. In a cruising superyacht it was a handful, especially when we ended up with Bucket Issues – not as in the race but as in the bucket and spinnaker sock that is used to snuff these massive asymmetric sails.  She wouldn’t go up and then she wouldn’t go down and then she wouldn’t go up and then we twisted the spinnaker HARD.  Just after we averted a shrimping incident I ran up to the bridge only to find Meteor headed towards us on Starboard.  We immediately started the gybe, which is NOT a fast process on these boats and just as our main flopped over they radioed ‘Consider Yourself Protested!’.  Our day didn’t get much better. After the finish as we had some mainsail issues and had to take her off of the mast.  This sail must weigh in over 1000lbs.

Thousand Pounds of Mainsail on the deck

We got to the dock only to rush up to defend ourselves at the protest meeting.    It was a very hard one to defend being a Port / Starboard and two of the jury weren’t really familiar with the operation of the different boats and we lost.  At that point I also knew that the owners had decided not to race and go to the beach on Sunday … with the boat!

I tired to put a positive spin on the day to the rest of the team but it was difficult.  We managed to get home and take a shower and the girls decided to put party dresses, with a smile on our face and head into town.  Meg and Suzy decided that they weren’t going to sail the final day but I knew if I was sitting on the beach watching the races I was going to feel horrible.  Luckily enough one of our team, James knew the captain of a 56 meter Perini named Panthalassa and they had two spots open, for me and James.  I told them that I was keen as long as they did need me.  I wasn’t into sitting around drinking champagne. At least not when racing!

Sunday morning I didn’t work out, and I was a little bit nervous.  I was also momentarily jealous of my roommate Suzy still sleeping and with a glorious beach day ahead of her.  I got to the boat and we left the dock and we got stuck into racing.  Very quickly my reservations all lifted and I slotted into the bridge with Pablo steering and Talpi tactician and Greg and Captain Greg as the safety officer and Clive navigating it was amazing to be surrounded by a tight team of great sailors and I was honored to be accepted in on the last day in the role of strategist.

The Fleet Behind Us

We had a great start and started working our way through the fleet, picking off the other boats one by one.  We came around the corner of the island and were happily in 4th place in fleet an 1st in class by a long way – like 20-minute lead!  Going into the day we had to beat the boat in 1st and put 3 boats in between us to win.  Unfortunately there ended up being only two boats in between so we tied in class and they won the tiebreaker but it didn’t really matter.  We had done the best we could.  We won the race and we ended up 2nd in class and we won the Perini Cup as the Perini Navi who finished highest in the overall standings.

There was a little bit of celebration!  I didn’t swim with a turtle or dance on the table 6” from Jimmy Buffett but the evening turned out to be extra special none the less.

It also turned out that it was a very good thing I had been hiking the mountains as on Sunday night the taxis really don’t run and Pablo and I ended up hiking up all the way past the airport and up and down two more crests to get to my apartment and car to go back and rescue the rest of the team so in the end I DID get my workout in and then some.

Monday I managed to miss my return flight and had a fun day with the Spaniards here are a few photos of the cultural experience they received 🙂

Pool Bars
And Beach Bars
Feeling the Jet Wash from a 747

So as I reflect I realize that there are some days and some regattas that are like slow train wrecks but then one good day of sailing and meeting like-minded good people who happen to sail and it is like sorbet for the mind.  We are truly blessed to do what we do!

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About Dawn

Dawn Riley is one of the best-known sailors in the world. She was the first woman ever to manage an entire America's Cup syndicate, the first American, man or woman, to sail in three America's Cups and two Whitbread Round the World races and is one of the forerunners in providing community access into the sport of sailing. See her biography for more information.

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Oakcliff Sailing Center
Raising the level of sailors and sailing in the US. Visit Oakcliff Sailing to learn more.



America True

Making sailing accessible to all.
Read more about America True.



America True DAY ON THE BAY at India Basin Shoreline Park



Ensuring Fair Play!
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