Driving Interest & Success in Junior Big Boat Sailing, Part 2

Story & photos by Rick Bannerot

Some sailors are born into it. Others wander in by accident, and then there are those who moved up from dinghies to the world of “big boat” sailing. The November/December 2021 edition of WindCheck recounted many notable junior big boat victories that generated headlines around the sailing world, including Young American winning the Vineyard Race in 2013, High Noon winning the 2016 Newport Bermuda Race, and Dreamcatcher’s victory in the 2018 Newport Bermuda Race (windcheckmagazine.com/article/the-rise-rise-of-junior-big-boat-sailing/).

Heady stuff, to say the least, but certainly not the be-all, end-all when it comes to making junior big boat sailing something that is not only fun, but also functionally instructive; building self-confidence, improving decision-making, and fostering more lifelong sailors.

A frequently mentioned goal is encouraging more young people to “go to sea.” Beyond that, regardless of the various paths available, is to have young men and women develop a sense of pride and identity themselves as “sailors” not only as teenagers, but eventually as adults.


Young American at the start of the Block Island Race   © Rick Bannerot/OntheFlyPhoto.net


Talking with Peter Becker (Founder of the Young American Sailing Academy and the Young American Foundation in Rye, NY), about his experience with juniors on big boats, he keeps coming back to the concept of young sailors “becoming salty” to describe gaining effective problem-solving techniques, learning and using sailing skills appropriately, and developing confidence. Becker strives to make the rather daunting idea of teaching teenagers to transition from going for a sail on a big boat into a teaching/learning process that breaks down the roles and responsibilities of the entire crew so they can all eventually sail the boat as a team.

From one side of Long Island Sound’s successful junior big boat sailing programs, we cross to Oyster Bay, NY where uber-accomplished sailor Dawn Riley is the Executive Director of Oakcliff Sailing. She has envisioned and successfully willed into existence through grit, determination, sweat equity, brains, fundraising, business acumen and no small amount of well-earned self-confidence what we see today.

Listening to Dawn speak about her experiences becoming a big boat sailor at a young age, you quickly come to understand she was raised in a big boat family and learned, literally at her father’s knee, onboard their 36-foot Great Lakes Cutter and then a “racier” C&C 35, around Michigan. Dawn cut her bluewater teeth at 13, sailing from Detroit to the Caribbean and back with her family, and earned her captain’s license at 15.

Oh, then were some of those other “offshore stints” like doing the Whitbread Round the World Race at the tender age of 26 on Maiden, as documented in the excellent film of the same name. Dawn was named skipper of Heineken in the ‘93-‘94 Whitbread before she turned 30, which is recounted in her first book, Taking the Helm.

Of particular interest is how she continues to be influenced by her experiences, whether racing dinghies at Michigan State, Whitbreads, crewing on the Maxi Matador, or being deeply involved in three America’s Cup campaigns (in a multitude of positions and responsibilities on and off the water). To be successful, Dawn firmly believes most people need to have a sailing vocation, as well as a passionate avocation, regardless of the boats they “like to sail.” Addressing the best young junior women Laser Radial sailors at US Sailing’s Leiter Cup at Stamford Yacht Club in 2018, she noted (with a knowing twinkle in her eye), “Very, very few people are paid to sail a 420 or a J/24.”

Dawn’s vision, which she has turned into reality at Oakcliff, is to bring a holistic learning approach to not only junior big boat racing, but also to match racing, foiling dinghies, cats and boards, and classic yachts, not only making better sailors and also teaching them how to work and make a living in almost any aspect of the industry.

Oakcliff accepts trainees (known as “Acorns” or “Saplings” depending on the program) from absolute beginners to seasoned racers, but Riley believes in a Socratic process of self-selection: “Am I good enough?” as well as the pure motivational standpoint: “Do I want it badly enough?” Sailors as young as 15 come and learn to sail a huge range of boats from 49ers to Match 40s and offshore racers.

Oakcliff schedules a mix of sailing, boat work, and physical training while encouraging and supporting trainees that show initiative in their own sailing-related projects, whether it be learning the art and skill of making period-perfect cotton sails for classic sailboats, learning to write software for state-of-the-art CAD/CAM sail design, acquiring the knowledge to manage a sailing team, or becoming a qualified boat captain.


This Class40 is one of many boats on which Oakcliff Acorns and Saplings gain offshore experience.  © Rick Bannerot/OntheFlyPhoto.net



The results generated by Oakcliff’s program in the last decade are impressive, ranging from a slew of racing sailors working in, and even running sail lofts (when not racing), and successfully fielding the first ever all-women’s team in the offshore double-handed Atlantic Cup. Oakcliff juniors have participated in several offshore events including the Newport Bermuda Race, Marblehead to Halifax Race, Ida Lewis Distance Race, Block Island Race, Vineyard Race and the Around Long Island Regatta (which an Oakcliff team won in 2021.)

“Most everyone comes here knowing what they want to do,” says Riley, “but they leave with so much more!” To that point, a popular t-shirt around the Oyster Bay campus and Oakcliff boats proudly proclaims one of Dawn’s key philosophies: “Oakcliff Sailing…Too Good to be True!” One can’t help but be reminded of a similar quote from Muhammad Ali, “It ain’t braggin’ if you can back it up.” And Oakcliff is certainly is backing up their view on sail training with real results. Just ask sailors like Charlie Enright and Sean O’Halloran (11th Hour Racing), Cormac Murphy (US Match Racing), Elizabeth Shaw (Atlantic Cup), and Robyn Lesh (American Magic).

Another key component to getting more young sailors involved in big boat sailing and dynamic race training experiences, is “simply” getting access to boats that are not only safe, but also able capable of racing ‘round the buoys (i.e. a local “Summer Tuesday Night Series” or the Junior Sailing Association of Long Island Sound’s annual Dorade Race, as well as offshore distance events like their Beach Point Overnight Race. Oakcliff has appropriately equipped charter boats for both. To charter for junior big boat sailing programs, the boats need to have their own qualified adult sailors onboard and working with the juniors to get them up to speed. For up-and-coming programs, Oakcliff can provide experienced sailors to provide additional training, coaching and mentoring.

Sailing (virtually) back to the northern side of the Sound, as promised, there are some valuable lessons learned over the course of the development of the Young American Sailing Foundation. Some of these are external land-based learnings, while others are gleaned in the space between the forestay and the tiller/wheel.

For a junior big boat program just getting started, one of the most common misconceptions Peter Becker has observed is “a misplaced emphasis on what boat to use.” Inevitably, it seems, the shoreside decision-making process leans towards a boat that ‘should be fast’ rather than a boat this is forgiving and can be tuned extensively for different kinds of sea and wind conditions, both with the rigging and the sails available. This gives young sailors the opportunity to get involved in learning boat dynamics, and they can see for themselves what works and doesn’t work. This not only builds ‘ownership’ in the decision-making process, it teaches them to think and to solve problems. A boat is but a tool; pure speed is not the first need. It has to be a focus on the ‘how’ and ‘what it takes’ to make the tool work…then learn how to let the tool be the best tool it can be.”

“Hire or utilize instructors that are not only experienced bluewater big boat sailors, but are also familiar, skilled, and enjoy teaching teenagers,” Peter continued. “Too often junior big boat programs, especially under the auspices of well-intentioned yacht clubs (or adult members with altruistic deep pockets and juniors they’d like to see gain some big boat experience) take on the responsibility of getting the program going within or in parallel with a club’s junior sailing program.”

“Too frequently they put the junior sailing instructor with ‘some big boat experience’ in charge of coaching the juniors in the big boat program. Unfortunately, this is almost always a recipe for failure in the long haul. There are actually very few skilled big boat instructors with the experience, passion and patience to effectively teach teenagers the art and science of big boat sailing, let alone racing. If you find one, hire them and pay them well. They are worth every penny, and then some.”

Under Peter Becker’s leadership the Young American Sailing Academy has introduced quite a number of junior sailors to big boat sailing, and assembled both successful (and by his own admission, some not-so-successful) racing teams. Peter draws some interesting conclusions about team dynamics, what makes for a “good team” versus a “great team,” and how quickly it can occur (in both directions). Having great big boat instructors that relate well with young sailors is a fundamental element, but it goes beyond that.

An interesting observation that Peter routinely puts into practice is building a mixed crew of young men and women. He finds they usually work better as a team, especially in offshore sailing and distance races. Testosterone-rich boats may be fast on occasion, thanks in part to the collective strength being applied during sail changes and grinding winches, but the presence of young women often brings fresh new analytical skills, and frequently better intuition on both driving a boat with, and actually flying a spinnaker. One only needs to look around a downwind start of a Vineyard Race to see how many women are handling the spinnaker sheet, calling the start sequence on the bow, and helming the boat as they fly down Long Island Sound.

Successful mixed teams have a very high level of respect for each sailor’s particular skills and special flair, whether it be intuitively calling wind shifts, sensing foul currents, playing a spinnaker sheet “just so,” or effectively synthesizing a weather report with the conditions at hand and making the optimal tactical calls. Peter has also noticed that when conditions get “snotty” for an extended period of time, the young women usually outnumber young men in terms of their physical endurance on deck and their positive attitudes throughout the boat. When young men see the exemplary examples being set by their female counterparts, the results can go either way. Usually, the guys suck it up and pitch back in; other times, not so much…and the whole process of effectively sailing a big boat starts to fall apart.

As part of the team-building approach, Young American’s sailors are actively encouraged to have full run of the boat, essentially a “free-range jungle gym” and have any position on the boat be a learning opportunity, even if they learn they do not “like” doing a particular job. No position should be off limits. At least they learn how to do it and should they be needed to fill in, they can. The added bonus is the respect it engenders when someone else on the crew does a job someone else isn’t as keen on doing. (Obviously, the exception to this in the aforementioned points is that during particularly adverse weather or sophisticated sailing maneuvers specific young sailors that have not yet learned these finer points should first be exposed to it in less stressful situations, and once they have demonstrated their understanding and competency, only then will they will be better prepared to test new, higher limits.)


Successful mixed teams, like the crew of the C&C 30 Spicy, develop much respect for each sailor’s particular skills. © Rick Bannerot/OntheFlyPhoto.net


An “all hands on deck” (and in the sewer, or the pit, or standing a midnight-to-0400 watch) philosophy underlies the process of becoming “salty.” “Obviously it takes time, patience, encouragement and support from the experienced big boat sailing coaches and mentors,” Peter asserts. “One sure sign of a crew beginning to gel and move towards synchronous teamwork is when the more experienced sailors begin to take on the mentor’s role with less experienced teammates and explain the ‘how and why’ to do something, or show a personal ‘hack’ they use to make something better.”

These experiences and teaching moments are part of the process for appearing to casually toss the equivalent of the “keys to a Ferrari” to junior sailors. In next month’s edition, we’ll see what’s it like for a young sailor to actually “catch” those rather expensive keys. Please join us as we board a Beneteau Figaro 2 and seek to re-live the trepidation, making mistakes, gaining confidence, and learning how to lead a teenage team as they prepare for sailing not only around the buoys, but also overnight. Our profile is a 15-year-old high school sophomore who, by her own admission, came to really dislike sailing Optis, but “found her salt” on big boats. ■