Oakcliff Sailing

Oakcliff Sailing was founded in 2010 by Hunt and Betsy Lawrence to raise the caliber of sailing in the United States - and put American sailors back on top of the podium. Located on the North Shore of Long Island in Oyster Bay, we boast an expert collection of directors, coaches, and industry leaders; as well as the largest fleets of Nacra 17s, 49ers, 49er FXs, and Match 40s in the US. Our facilities include an impressive sail loft, rigging and composites shop, gym, and a state-of-the-art bunkhouse. Oakcliff continues to grow leaps each year, with programs ranging from inshore racing, to high performance, to offshore and match racing. Beginning in 2020, Oakcliff expanded to partner with the U.S Performance Academy to bring an accredited high school to Oakcliff’s campus in Oyster Bay. The clinics and coaching at Oakcliff are unparalleled thanks to the world-class staff and graduates. Executive Director Dawn Riley, who was the first American to compete in three America’s Cups and two Whitbread Round the World Races (now the Ocean Race), runs meetings, coordinates activities, fundraises, and lends her expert experience to trainees and staff. Board Member Dave Perry, a widely respected match racer, frequently hosts match racing clinics throughout the season. Thanks to our extensive resources, we are able to provide a wide variety of opportunities to every type of sailor. If you are looking for a short-term program specifically designed for high-performance dinghy sailing, offshore sailing, match racing, or Maxi yacht racing, you might consider the Acorn Programs. Adults interested in getting involved can look into our program intensives or consider becoming an Oakcliff Supporter. To read more about our history: