Oakcliff Sailing Center is shaping the future of competitive sailing, and at the helm of this innovative training ground is Dawn Riley—one of the most accomplished figures in the sport. In this interview, Riley shares insights into Oakcliff’s unique programs, the skills they develop, and how the center is preparing the next generation of sailors and industry professionals for success on and off the water.
Article by Ty Christopher Olsen, March 10, 2025.
Inside Oakcliff: Dawn Riley on Training the Next Generation of Sailors
TCO: Your sailing career is marked by incredible achievements, including being the first female to manage an America’s Cup team, competing on four America’s Cup teams, leading two Whitbread Round the World teams, and serving as president of the Women’s Sports Foundation—just to name a few. What drew your interest to Oakcliff?
DR: Well, in addition to those you mentioned, I was also inducted into the Michigan Sports Hall of Fame, adding to my honors in the National Sailing Hall of Fame and the America’s Cup Hall of Fame.
What brought me to Oakcliff Sailing is interesting. Sixteen years ago, the Lawrence family invited me to Oyster Bay as a consultant, to look at some boats and equipment they had acquired. Together we created the concept of a national sailing center to serve aspiring athletes both on and off the water. Recognizing the need and more importantly, the potential for such a place, I agreed to a three-year role to help implement the vision. Thanks to a great plan and strong support, that vision has taken off—and now, 15 years later, I’m still working with them and Oakcliff has produced notable athletes and encompasses nearly every aspect of the sport.
TCO: Tell me what Oakcliff does and what programs that you guys offer.
DR: We have such an incredible range of programs that it can be overwhelming. We focus on racing, but also cover the technical aspects of sailing. One of our standouts is the Sapling Program, which is an apprenticeship designed for experienced sailors who want to advance in the sport. It provides a comprehensive sail and job training, allowing athletes to explore all areas before focusing on their specific path of being a collegiate sailor or coach, a professional boat captain or a boat owner.
We also offer the Acorn Program, tailored for sailors aged 15 and older. This program provides a well-rounded curriculum that includes on-the-water training, race preparation, physical conditioning, and classroom sessions in a specific area, offshore, high performance or match racing.
The Sapling and Acorn programs are just two of our most popular offerings. In addition, we provide specialized training in high-performance racing, offshore racing, boat repair, and a range of technical disciplines. Our hands-on curriculum equips students with essential skills, including small line splicing, composite repairs, winch maintenance, sail making, and engine and electronics work. Whether you’re aiming to compete at the highest level or develop expertise in boat maintenance and repair, our programs offer the knowledge and experience you need to excel.
TCO: I can imagine that you have some challenges with the weather up in Oyster Bay, do the programs run year around?
DR: Yes, our programs do run year-round. The Sapling Program is customizable, with fall, spring, and summer semesters. Participants are full-time, and during the fall and winter, they spend less time on the water and focus more on sail-making, electronics, composites, program management, databases, accounting, and other essential business aspects of the sport.
In the summer, the emphasis shifts heavily to on-the-water training, making it harder to dedicate time to administrative skills—though these are crucial, especially for those considering an Olympic campaign.
TCO: What facilities does the Oakcliff Center offer?
DR: We have a bunkhouse, a full-service gym, workshops, classroom facilities, and more. The center is essentially self-contained with everything a sailor needs. While staying in the bunkhouse isn’t mandatory, nearly everyone chooses to. In fact, over the past 15 years, only about seven people have opted to live elsewhere, and all of them ended up moving into the bunkhouse within three days. They quickly realized they wanted to be part of the team 24/7.
The camaraderie here is great. Early mornings, when the breeze is good, we often start with a sunrise sail, turning it into a fun challenge to see how quickly everyone can get on the water. We sail until about 10:30 a.m. when the wind is best, then come in for breakfast, do some boat work, hit the gym, and head back out in the evening to catch the second-best breeze of the day at sunset. There’s always something to do—if the wind is too strong, we’ll get out on a WASZP; if it’s too light, we’ll tow out some Nacra 17s. And when the conditions aren’t ideal for sailing, we might even set up a game of rugby in the water with a greased watermelon. There’s not a lot of down time.
TCO: With such a broad range of programs, covering just about every angle of sailing, how many instructors or staff do you have on hand?
DR: Right now, we’re operating with a small team—just eight staff members managing 100 boats. Many of our instructors are graduates, who we hire back to take on various roles. Additionally, some of our programs, particularly those involving high-performance boats or Olympic-class boats, are led by contract coaches.
Our resources can be stretched thin at times both internally and externally. It is surprising how many people don’t realize the high demand for experienced professionals in this industry. Just this morning, I spent a good portion of my time working with the Navy and Bayview Yacht Club, both of whom reached out for help finding qualified personnel. There are so many opportunities available, and often when someone needs a skilled individual, they call us first. These are just two of the many respected organizations that regularly contact us looking to fill well-paying senior positions in the sailing industry.
TCO: How do sailors get involved with Oakcliff? Is there a recruitment process or is it all application based?
DR: Our program is entirely application-based, and we offer need-based scholarships. If you have the talent and the means to pay, go for it! But if you have the motivation and need financial support, we have scholarships in place to make it happen. Our mission is to train sailors and set them free to pursue their goals.
One of the unique aspects of Oakcliff is that we focus on long-term development unlike many youth coaching programs that prioritize immediate results. Too often, young sailors are pressured to win the next regatta or the next Youth Worlds because coaches are operating with a short-term mindset—focused on producing immediate champions to boost their reputation and income. That approach is flawed. At Oakcliff, we’re here for the entire journey. We never tell our athletes to “go out and crush the competition.” Instead, we emphasize having fun, learning, thinking critically, and putting in maximum effort. When sailors focus on those fundamentals, winning becomes a natural outcome.
Our approach is the opposite of the many programs, which often prioritize only top performers while overlooking those who are putting in their best effort. Those programs see nearly 50% of sailors dropping out, wasting an incredible amount of potential talent. This issue is particularly evident among female sailors. Girls tend to mature earlier and excel in smaller boats like Optis, often overachieving at a young age. However, as they stop growing physically, they may not fit into roles like 49er FX crews and conversely if they outsize an Opti early – they are pushed out into the wild with no support and also wash out of sailing. This is a well-documented pattern, yet I still face resistance from professional coaches when I try to discuss it with them.
TCO: Out of the broad range of programs that Oakcliff offers, is there one that is sought after over others?
DR: I would say that the Match Racing program is definitely up there in terms of popularity. Oakcliff Sailing has earned a reputation as one of the top match racing centers globally. We are lucky to have the World Match Racing Tour endorse our program. One young standout sailor who came through our program is Timothee Rossi from France, who joined about two years ago. He’s now ranked in the top 10. Another popular program is our Offshore Racing Program. Just last year, we sent 95 Oakcliff sailors on the Newport to Bermuda Race.
The hardest program to fill is our High-Performance Program. This is mainly due to the fact that it tends to attract younger sailors who are just discovering their path. Many of these aspiring high-performance racers initially focus solely on a narrow aspect of the sport. When they join us, it’s often a challenge to help them open up to the broader world of sailing and realize that there’s much more to the sport than just high-performance racing. That said, we are fully supportive of the high-performance world, and if there’s a demand, we will do everything we can to provide the necessary resources to meet it.
TCO: On average, how long are the programs that you offer?
DR: The shorter programs last about 10 days, while the Offshore Programs run from 3 to 5 weeks. If you’re enrolled in the Sapling Program, some schedules may overlap, but you’ll have the flexibility to choose your activities—we make it work. For example, if a High-Performance Program is running on-site while you opt for an offshore program, we might arrange an overnight trip around Long Island for the offshore group to free up bunk space. When you return, you can jump right onto a Nacra.
TCO: What about the Oakcliff fleet, what classes of boats do you have to offer?
DR: Our extensive fleet is entirely donated and includes a diverse range of vessels. We start with UFOs, Lasers, Sunfish, and various beach boats, followed by a fleet of WASZPs, 49ers, FX, Nacra 17s and 20s, 470s, Melges 24, Shields, and Match 40s. Additionally, we have four Farr 40s, a Class 40s, and various shorthanded offshore boats. Among our larger vessels, we boast a Ker 50, a JV 66, OC86’ the “old” Windquest. And, I am sure that I might be forgetting some! Suffice it to say, our fleet is impressive—we often joke with the Navy about who has more boats!
TCO: Does Oakcliff have boats for charter to individuals that are not involved with the program?
DR: Yes, we do offer boats for charter, but specifically to Oakcliff alumni. While we have occasionally chartered to individuals and organizations outside of our network, it hasn’t always worked out well. We believe that alumni, having gone through our training, are not only skilled sailors but also know how to care for the boats properly. This gives us greater trust in them.
We encourage our graduated alumni to charter our boats for a season down south, or wherever. We will even help them with the program in organizing and preparing.
In addition to the boats for charter, we do have a few of the boats that are not being actively used, that are for sale.
TCO: With all of the sailors that have gone through the different programs that you offer, what are some of the more notable success stories?
DR: There have been many successes, at all levels. Olympians Ian Barrows and Hans Henken both sailed here. If I remember correctly, the first time Ian stepped on a skiff was here at Oakcliff. Both Paris Henken and Anna Tunnicliffe trained here with the high-performance group, and all the Olympic Class 470 sailors sailed here as well. Then there’s Mark Towill and Charlie Enright who won The Ocean Race, and Canadian Peter Wickwire, who is now ranked 8th in the world. Chris Poole and Gavin Brady also race regularly here.
We have many great success stories, but Oakcliff offers more than just sailing. We provide athletes with valuable leadership skills, teambuilding, hands-on marketing, and general skills that can be applied throughout their lives.
Dawn, thank you for taking the time, especially during your vacation! I hope that you guys continue to have the same success that you have over the past several years. We will be looking for the names of future professional sailors coming from Oakcliff.
