About Oakcliff

Founded in 2010 by Hunt and Betsy Lawrence in order to raise the caliber of sailing in the United States, Oakcliff Sailing has grown by leaps and bounds each year from offshore racing to high performance as well as inshore racing. Based in the North Shore of Long Island in Oyster Bay, Oakcliff hosts sailors from around the world filling the bay with sails through the summer.

Sailing in the United States is in trouble, Oakcliff is here to help.

America may have made the greatest comeback in sports history in the Fall of 2013 when Oracle Team USA came from behind to beat Emirates Team New Zealand with eight consecutive wins to successfully defend the America’s Cup.  But all is not well. The United States had just one sailor onboard for the victory. And in the London 2012 Olympic Games, sailors from the United States brought home the fewest Olympic medals since 1936. In 2016 we managed one but we still have a way to go. Sailing in the United States is in trouble and Oakcliff is stepping up to fight this problem.

US Sailing Match Race Championship 2015What resources does Oakcliff have to offer?
Without exploring what Oakcliff Sailing has to offer, it might seem to be a lofty goal to restore American sailors to the top of the podium. But, with an expert collection of directors, coaches, industry leaders, and alumni, Oakcliff Sailing is the best suited sailing center in the country to do so. Sailors at Oakcliff have access to nearly 100 boats, including the largest worldwide fleets of Nacra 17s, 49ers, 49er FXs, and  Match 40s. In addition to a fantastic fleet, a sail loft, and a workshop, the clinics and coaching at Oakcliff Sailing are also unparalleled. On a daily basis, students are coached by staff and world-class top coaches. The first American to compete in three America’s Cups and two Whitbread (now Volvo) Races, Executive Director, Dawn Riley, runs daily meetings and coordinates activities. Meanwhile, board member Dave Perry, who has written several books on sailing and match racing also leads match racing clinics throughout the season.

What is already happening at Oakcliff?


While Oakcliff Sailing is only in its first decade, it already boasts some remarkable success stories.  Oakcliff Sailing consistently over achieves:

  • Oakcliff  Sailing is  an official training center of the US Sailing Team
  • Boasts  the world’s largest collection of Olympic class Nacra 17s, 49ers, and 49er FXs
  • Hosts more match racing events than anywhere else in the country
  • Organized and hosted 19 regattas including the Nacra 17/49er/49erFX US National Championship and the Oakcliff International
  • Celebrates multiple podium finishes for Oakcliff Sailing Offshore Teams
  • Sends 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 many more.
  • Oakcliff also has sent teams to support the Volvo and America’s Cup World Tour.

Want to get involved?

One of the great parts of Oakcliff Sailing is that with tremendous growth comes huge opportunities. If you are looking for a short term program focused on a specific area of the sailing industry, you might consider one of the Acorn programs specifically designed for high performance dinghy sailing, offshore racing, or match racing. Experienced sailors who are looking for an intensive program to cover a wide variety of topics are perfect candidates for the Sapling program, an intensive summer – long program which covers everything from advanced match racing and sail repair to composite work and offshore navigation. Adults interested in getting involved can either consider becoming a supporter or applying for the Custom Acorn program. If you are interested in attending a clinic or racing in a regatta at Oakcliff Sailing, please check our calendar to register.