About Oakcliff

Oakcliff Sailing Mission Statement:
Oakcliff is dedicated to building American leaders through sailing by providing coaching, mentorship and job training both on and off the water.

Core Values:
In the execution of our Strategic Plan, we agree to stay true to our Core Values:
1. Quality & Excellence
2. Innovation & Continuous Improvement
3. Honesty & Integrity
4. Sound Environmental & Fiscal Stewardship
5. Fairness & Respect

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 Oakcliff Academies, specifically designed for high performance dinghy sailing, offshore racing, match racing and Maxi yacht racing. Adults interested in getting involved can sign up for one of the Academy intensives or consider becoming a supporter. If you are interested in attending a clinic or racing in a regatta at Oakcliff Sailing, please check our calendar to register.

Oakcliff – A Ten Year History

The idea for Oakcliff Sailing, as it is known today, was proposed to Hunt and Betsy Lawrence by their family in July of 2009. Lifelong sailors and lovers of the history and traditions of sailing, the Lawrence’s envisioned creating a national sail training organization that would help fill Oyster Bay with boats, and ideally raise the level of sailing throughout the United States.

To accomplish this vision they set about assembling the pieces needed, working from the ends of what was available. The Lawrence’s provided an unprecedented donation of floatable assets and financial commitment to launch the project. The Oakcliff Yacht Center (OCYC) was incorporated that September as a transition towards a new organization. This created steady employment for the many craftspeople the Lawrence’s previously employed in what had been a small unarmed navy. Oakcliff’s officers were David Halliwill, and Bryan Lawrence, and the original trustees included: Donn Costanza, David Halliwill, Bryan Lawrence, Corey Lawrence, Dave Perry, Dawn Riley and Ralf Steitz. Oakcliff Sailing was incorporated on February 25, 2010, and OCYC was later dissolved.

Dawn Riley accepted an offer to consult with OCYC on the new not-for-profit venture on November 16, 2009, and in January 2010 she was hired as Executive Director. Dawn’s 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, made her uniquely qualified to manage Oakcliff. The team at Oakcliff is currently just over ten people.

In the years immediately prior to Oakcliff’s formation there were quite a few avid sailors in the area working for Hunt Lawrence on his boats, or for John McGrane at the Oyster Bay Marine Center. They became the nucleus of the workers and sailors at OCYC and then Oakcliff Sailing, which occupies the buildings on the end of South Street in Oyster Bay. Bill and Gina Niedringhaus, Ladi Oguntoyinbo, Colin Bunell, Andrew Wills, Ronnie Saccardo and others maintained and raced on the Oakcliff “fleet” of boats, which included 6 Match 40’s, 6 Shields, 6 Melges 24’s, 6 Lasers, 2 Farr 40’s, several Ker designed boats and an assortment of powerboats.

Years before, Hunt had fallen in love with match racing and saw an opportunity to increase America’s international match race rankings and to create the next great American America’s Cup skipper. To that end he has purchased eight Match 40’s and has had four more built. These were purpose-built boats being used on the World Match Racing Tour at the time. Between Oakcliff and Hunt, there are now 12 evenly matched Match 40s that actively race in Oyster Bay, and the Oakcliff International is once again a part of the World Match Racing Tour. Oakcliff is also now a partner with Magic, the New York Yacht Club’s challenger for the 2021 America’s Cup.

In 2012, 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. The programs were restricted to adults, 18 years or older.  

The following summer, after significant pressure to include younger sailors, the team renamed the summer-long program the “Sapling program” and created a series of shorter Acorn sessions with specialties such as offshore, fleet and match racing, high performance and foiling and even on-board reporter training.  Programs are coached by both Oakcliff staff and outside experts. These shorter sessions are most attractive to teenagers or older sailors who have shorter periods of time available.

The summer-long Sapling program is for those who want to become leaders in the marine industry or sailing professionals. Saplings spend several months, and in some cases several years, learning and working across all aspects of the marine industry. Oakcliff Saplings are now working and sailing on America’s Cup and Ocean Race teams, managing sail lofts and rigging shops, and running offshore racing programs around the world.

Oakcliff has become a world class training center that has graduated over 300 sailors. Jacon’s dream of having an on-site dormitory to house trainees and event participants came true when the Bunkhouse was built upstairs at 4 South Street in 2016, which can house up to 40 sailors. Downstairs there are offices, the boat shop and a sail loft. Next door at 2 South Street is a multipurpose event space for classrooms large meetings and social gatherings. Across the street is a yard for boat storage and repair. Sailors and staff at Oakcliff have access to a cross-fit gym nearby, and Oakcliff has a High Performance beach with direct launching access to Oyster Bay for their ever-growing fleet of Olympic Class boats.

After an unsuccessful 2012 Olympics for the US Sailing Team, Hunt challenged Oakcliff to put American sailors back on the Olympic podium. Oakcliff’s fleets quickly grew to include most all of the current Olympic classes like the 49er, 49erFX and foiling Nacra 17s, 470s, Lasers and Finns. The high performance fleet also has Nacra 20s as well as the foiling Waszps. Oakcliff partners closely with the US Sailing and Olympic Development Teams and regularly hosts training camps and development regattas to assist the US Olympic sailing development.

Also associated with Oakcliff are over a dozen venerable classic yachts which regularly race in Oyster Bay, with social gatherings afterwards hosted at Oakcliff. On a Thursday evening in the summer it is not unusual to see the Newport 29’s Dolphin and Mischief sail by, followed by Nautilus (a NY 30) and Oriole II (a 30 sq. meter yacht).

Alongside its educational, one-design, offshore and Olympic development programs, Oakcliff runs a robust program for its supporters with casual evening racing, coached evening match racing and weekend regattas.

The Oakcliff Board has grown to nearly a dozen trustees representing all aspects of the sport and development programs for not-for-profit organizations. Oakcliff relies on its supporters and programs for over two-thirds of its revenue and is always looking for people who share its vision to help support its mission as it begins its next ten years of service to the sport.