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. The programs include both shorter Acorn sessions and longer options such as a summer-long Acorn session and a summer-long Sapling program, with Acorn Programs focused on high-performance dinghy sailing, offshore racing, match racing, and Maxi yacht racing. The Sapling program is for those who want to become leaders in the marine industry or sailing professionals, and Oakcliff has graduated over 300 sailors.
• Ages: 15–18 years old
• Schedule: Short-term programs, shorter Acorn sessions, a summer-long Acorn session, and a summer-long Sapling program
Oakcliff Sailing Programs were founded in 2010 by Hunt and Betsy Lawrence after the idea for Oakcliff Sailing was proposed in July 2009 and Oakcliff Yacht Center (OCYC) was incorporated in September 2009. Dawn Riley accepted an offer to consult with OCYC on November 16, 2009, was hired as Executive Director in January 2010, and Oakcliff Sailing was incorporated on February 25, 2010. Oakcliff Sailing is just over fifteen years old, and the Bunkhouse used by the program was built in 2016. Oakcliff’s officers at incorporation of OCYC were David Halliwill and Bryan Lawrence, and the original trustees were Donn Costanza, David Halliwill, Bryan Lawrence, Corey Lawrence, Dave Perry, Dawn Riley, and Ralf Steitz.
The program’s mission is stated as “Oakcliff’s goal is to Build American Leaders Through Sailing.” Oakcliff 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, and it accepts trainees with a wide variety of skill levels at a wide range of ages, from absolute beginner sailor to seasoned racer. The training environment is flexible, with program schedules that mix sailing, boat work, and physical training, and trainees are encouraged to pursue their own projects and interests such as sailmaking, managing a sailing team, or becoming a boat captain.
Oakcliff has an expert collection of directors, coaches, industry leaders, and alumni, and clinics and coaching are provided daily by staff and world-class top coaches. Executive Director Dawn Riley is the first American to compete in three America’s Cups and two Whitbread (now Volvo) Races and has experience as 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 and leads match racing clinics throughout the season. 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. Programs are coached by both Oakcliff staff and outside experts.
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 boasts the world’s largest collection of Olympic class Nacra 17s, 49ers, and 49er FXs and hosts more match racing events than anywhere else in the country. Sailors at Oakcliff have access to nearly 100 boats, including large fleets of Nacra 17s, 49ers, 49er FXs, 470s, ILCAs, and Match 40s, and there is a High Performance beach with direct launching access to Oyster Bay for an ever-growing fleet of Olympic Class boats. The on-site dormitory, called the Bunkhouse, can house up to 40 sailors.
Oakcliff Sailing is an official training center of the US Sailing Team, 11th Hour Racing, NYYC American Magic, IYRS, and the World Match Racing Tour, and is a partner with Magic, the New York Yacht Club’s challenger for the 2021 America’s Cup. Oakcliff hosts sailors from around the world and organized and hosted 19 regattas including the Nacra 17/49er/49erFX US National Championship and the Oakcliff International. Oakcliff has sent competitors to grand prix events including the Mini Transat, Red Bull Youth America’s Cup, World Match Race Tour, Farr 40 Worlds, Caribbean 600, and many more, and has sent teams to support the Volvo and America’s Cup World Tour. Oakcliff Saplings work and sail on America’s Cup and Ocean Race teams, manage sail lofts and rigging shops, and run offshore racing programs around the world.
Last updated February 8, 2026.
• Ages: 15–18 years old
• Schedule: Short-term programs, shorter Acorn sessions, a summer-long Acorn session, and a summer-long Sapling program
Oakcliff Sailing Programs were founded in 2010 by Hunt and Betsy Lawrence after the idea for Oakcliff Sailing was proposed in July 2009 and Oakcliff Yacht Center (OCYC) was incorporated in September 2009. Dawn Riley accepted an offer to consult with OCYC on November 16, 2009, was hired as Executive Director in January 2010, and Oakcliff Sailing was incorporated on February 25, 2010. Oakcliff Sailing is just over fifteen years old, and the Bunkhouse used by the program was built in 2016. Oakcliff’s officers at incorporation of OCYC were David Halliwill and Bryan Lawrence, and the original trustees were Donn Costanza, David Halliwill, Bryan Lawrence, Corey Lawrence, Dave Perry, Dawn Riley, and Ralf Steitz.
The program’s mission is stated as “Oakcliff’s goal is to Build American Leaders Through Sailing.” Oakcliff 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, and it accepts trainees with a wide variety of skill levels at a wide range of ages, from absolute beginner sailor to seasoned racer. The training environment is flexible, with program schedules that mix sailing, boat work, and physical training, and trainees are encouraged to pursue their own projects and interests such as sailmaking, managing a sailing team, or becoming a boat captain.
Oakcliff has an expert collection of directors, coaches, industry leaders, and alumni, and clinics and coaching are provided daily by staff and world-class top coaches. Executive Director Dawn Riley is the first American to compete in three America’s Cups and two Whitbread (now Volvo) Races and has experience as 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 and leads match racing clinics throughout the season. 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. Programs are coached by both Oakcliff staff and outside experts.
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 boasts the world’s largest collection of Olympic class Nacra 17s, 49ers, and 49er FXs and hosts more match racing events than anywhere else in the country. Sailors at Oakcliff have access to nearly 100 boats, including large fleets of Nacra 17s, 49ers, 49er FXs, 470s, ILCAs, and Match 40s, and there is a High Performance beach with direct launching access to Oyster Bay for an ever-growing fleet of Olympic Class boats. The on-site dormitory, called the Bunkhouse, can house up to 40 sailors.
Oakcliff Sailing is an official training center of the US Sailing Team, 11th Hour Racing, NYYC American Magic, IYRS, and the World Match Racing Tour, and is a partner with Magic, the New York Yacht Club’s challenger for the 2021 America’s Cup. Oakcliff hosts sailors from around the world and organized and hosted 19 regattas including the Nacra 17/49er/49erFX US National Championship and the Oakcliff International. Oakcliff has sent competitors to grand prix events including the Mini Transat, Red Bull Youth America’s Cup, World Match Race Tour, Farr 40 Worlds, Caribbean 600, and many more, and has sent teams to support the Volvo and America’s Cup World Tour. Oakcliff Saplings work and sail on America’s Cup and Ocean Race teams, manage sail lofts and rigging shops, and run offshore racing programs around the world.
Last updated February 8, 2026.
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