Oakcliff Sailing Programs
Oakcliff Sailing facility, 4 South Street, Oyster Bay, NY 11771
About
Oakcliff Sailing Programs include sailing, offshore racing, high performance sailing, inshore racing, high-performance dinghy sailing, match racing, Maxi yacht racing, foiling, on-board reporter training, boat work, and physical training. Program schedules include a mix of sailing, boat work, and physical training. Sailors at Oakcliff have access to nearly 100 boats, including large fleets of Nacra 17s, 49ers, 49er FXs, 470s, ILCAs, and Match 40s.
• Ages: 15–18 years old
• Schedule: Summer-long Acorn session, summer-long Sapling program, and shorter Acorn sessions
Oakcliff Sailing was founded in 2010 by Hunt and Betsy Lawrence after the idea was proposed in July 2009, and it was incorporated on February 25, 2010. Oakcliff Sailing is just over fifteen years old and has graduated over 300 sailors. Oakcliff Sailing is a youth and adult training center for athletes who have progressed beyond traditional coaching methods and want to take the next step in their career. Oakcliff accepts trainees with a wide variety of skill levels, from absolute beginner sailor to seasoned racer. Oakcliff’s summer-long Sapling program is for those who want to become leaders in the marine industry or sailing professionals and involves learning and working across all aspects of the marine industry. Programs have flexibility for trainees’ projects and goals, including interests such as sailmaking, managing a sailing team, or becoming a boat captain. Clinics and coaching are provided daily by staff and world-class top coaches.
Oakcliff’s goal is to Build American Leaders Through Sailing. Oakcliff is an official training center of the US Sailing Team, 11th Hour Racing, NYYC American Magic, IYRS, and the World Match Racing Tour. Oakcliff hosts more match racing events than anywhere else in the United States and organized and hosted 19 regattas including national championships and international events such as the Nacra 17/49er/49erFX US National Championship and the Oakcliff International. Oakcliff boasts the world’s largest collection of Olympic class Nacra 17s, 49ers, and 49er FXs. Oakcliff hosts sailors from around the world and sends competitors to events including the Mini Transat, Red Bull Youth America’s Cup, World Match Race Tour, Farr 40 Worlds, Caribbean 600, and others, and has sent teams to support the Volvo and America’s Cup World Tour. Oakcliff is a partner with Magic, the New York Yacht Club’s challenger for the 2021 America’s Cup.
Executive Director Dawn Riley is the first American to compete in three America’s Cups and two Whitbread (now Volvo) Races, and her experience includes being a professional sailor in the Whitbread Round-the-World Race and in the America’s Cup as a sailor, skipper, CEO and Team Manager. Founding board member Dave Perry has written several books on sailing and match racing. Graduate turned staff member Jacon Mayer used his experience as a NOLS instructor and his training in the beta Acorn program to re-design and run Oakcliff’s first summer-long Acorn session. Oakcliff’s leadership and founding group includes Executive Director Dawn Riley, founding board member Dave Perry, officers at incorporation David Halliwill and Bryan Lawrence, and original trustees Donn Costanza, David Halliwill, Bryan Lawrence, Corey Lawrence, Dave Perry, Dawn Riley and Ralf Steitz.
Last updated May 29, 2026.
• Ages: 15–18 years old
• Schedule: Summer-long Acorn session, summer-long Sapling program, and shorter Acorn sessions
Oakcliff Sailing was founded in 2010 by Hunt and Betsy Lawrence after the idea was proposed in July 2009, and it was incorporated on February 25, 2010. Oakcliff Sailing is just over fifteen years old and has graduated over 300 sailors. Oakcliff Sailing is a youth and adult training center for athletes who have progressed beyond traditional coaching methods and want to take the next step in their career. Oakcliff accepts trainees with a wide variety of skill levels, from absolute beginner sailor to seasoned racer. Oakcliff’s summer-long Sapling program is for those who want to become leaders in the marine industry or sailing professionals and involves learning and working across all aspects of the marine industry. Programs have flexibility for trainees’ projects and goals, including interests such as sailmaking, managing a sailing team, or becoming a boat captain. Clinics and coaching are provided daily by staff and world-class top coaches.
Oakcliff’s goal is to Build American Leaders Through Sailing. Oakcliff is an official training center of the US Sailing Team, 11th Hour Racing, NYYC American Magic, IYRS, and the World Match Racing Tour. Oakcliff hosts more match racing events than anywhere else in the United States and organized and hosted 19 regattas including national championships and international events such as the Nacra 17/49er/49erFX US National Championship and the Oakcliff International. Oakcliff boasts the world’s largest collection of Olympic class Nacra 17s, 49ers, and 49er FXs. Oakcliff hosts sailors from around the world and sends competitors to events including the Mini Transat, Red Bull Youth America’s Cup, World Match Race Tour, Farr 40 Worlds, Caribbean 600, and others, and has sent teams to support the Volvo and America’s Cup World Tour. Oakcliff is a partner with Magic, the New York Yacht Club’s challenger for the 2021 America’s Cup.
Executive Director Dawn Riley is the first American to compete in three America’s Cups and two Whitbread (now Volvo) Races, and her experience includes being a professional sailor in the Whitbread Round-the-World Race and in the America’s Cup as a sailor, skipper, CEO and Team Manager. Founding board member Dave Perry has written several books on sailing and match racing. Graduate turned staff member Jacon Mayer used his experience as a NOLS instructor and his training in the beta Acorn program to re-design and run Oakcliff’s first summer-long Acorn session. Oakcliff’s leadership and founding group includes Executive Director Dawn Riley, founding board member Dave Perry, officers at incorporation David Halliwill and Bryan Lawrence, and original trustees Donn Costanza, David Halliwill, Bryan Lawrence, Corey Lawrence, Dave Perry, Dawn Riley and Ralf Steitz.
Last updated May 29, 2026.
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