Sailing on the North Shore of Long Island offers a remarkable experience, where the blue waters of Long Island Sound meet the green coastline. Sailors glide gracefully along the gentle breezes, navigating past historic lighthouses and charming seaside villages. The coastline’s rugged beauty provides a picturesque backdrop as seafarers revel in the tranquility of the open waters.
Oakcliff Sailing Center in Oyster Bay has been capitalizing on this appeal since 2010 with two missions: to fill Oyster Bay with sails and to build leaders through sailing. I spoke with Dawn Riley, executive director at Oakcliff about this amazing opportunity. Here is what she had to share.
CH: Tell me about Oakcliff Sailing Center.
DR: There is nothing like Oakcliff or Oyster Bay sailing in the world; Oyster Bay is truly a golden gem on the Gold Coast. Oakcliff serves anybody who knows how to sail, on up to Olympic- and America’s Cup-level sailors.
CH: Who are your students and what makes a good sailor?
DR: We actively recruit through multiple scholarship funds, specifically at community sailing centers around the country. We are also looking for those who are interested in sailing but are from underserved communities. Interestingly, a lot of our students tend to come in clusters, like Wisconsin, Oklahoma and Southern California, usually by way of young people and word-of-mouth. Sailors are athletes; we work out regularly and sailing requires different skills for different types of sailing, but in general, sailors are fit and flexible; that is key. More than 50 percent of our graduates are in the marine industry, building boats, sailing in the America’s Cup and going on to the Olympics.
CH: What are people more surprised to learn about sailing?
DR: Younger sailors are surprised when they fall in love with the sport; they are teens and it helps them focus on one thing; they discover the wide breadth of opportunities that there are. Students love learning about how we train, how all the parts of the boat work, and managing the sails. They often leave with a completely different idea and career path.
CH: Describe sailing on the Long Island Sound.
DR: Some days are civilized and some days, like today [nor’easter on Wednesday, April 3], are wild and wooly. I went out to the beach this morning and it’s like the Southern Ocean [Antartic Ocean]. When you get a good nor’easter, it’s wild. You need two different skill sets to sail the Long Island Sound. You end up with two different [weather] masses, the north shore of Long Island versus the south shore of Connecticut. The sea breeze is quite tricky. Sailing Long Island Sound requires you to believe the unbelievable in terms of what the wind is doing, or could potentially do; this is a pretty good training ground for the finesse of the sport of sailing.
CH: Do you train with the students in this weather?
DR: If this weather was happening during the regatta, we would be sailing in it, so yes, no matter what the weather is doing. Last fall, it was blowing 30 knots and we sent students out knowing that it was going to be way past some of their limits. We train past the limits; we train on the schedule that we will compete on. Billie Jean King is a friend of mine and she talks about that when she speaks about “The Battle of the Sexes.” That’s exactly what we do. We train on the race schedule.
Riley is a renowned figure in the world of sailing, celebrated for her pioneering spirit and remarkable achievements. As one of the few women to break barriers in professional sailing, Riley has left an indelible mark on the sport. She is a member of the National Sailing Hall of Fame, the International America’s Cup Hall of Fame and the State of Michigan Sports Hall of Fame. She is the only person to achieve this.
Her impressive résumé includes four America’s Cup campaigns and two Whitbread Round the World races, making her one of the most experienced sailors globally. Beyond her competitive prowess, Riley is also a dedicated advocate for gender equality in sailing, empowering women to pursue their passions on the water. With her fearless determination and leadership, she continues to inspire countless individuals to chase their dreams and navigate uncharted waters.
Riley is the past president of the Woman’s Sports Foundation and is a much sought-after motivational speaker.
Oakcliff offers unique programs from corporate teambuilding to a tuition based residential program for athletes who want a career in the marine industry. Through these programs, Oakcliff is helping America regain its leadership position in the sport and “Building American Leaders Through Sailing.”
Oakcliff Sailing Center is located at 4 South Street in Oyster Bay. Visit www.oakcliffsailing.org to learn more.
