Oakcliff Sailing is an unparalleled training facility, sculpting the next generation of champions and leaders. Oakcliff’s programs have placed graduates in many of the top programs including multiple Round the World Races, the America’s Cup as well as sending many athletes to the Olympics in high performance classes.
Oakcliff surrounds you with fellow athletes and gives you the resources to push yourself to envision and reach entirely new horizons.”
— ANNA SEMS, High Performance High School Student
Located in Oyster Bay NY and led by Dawn Riley. Dawn raced in 4 America’s Cups and 2 Round the World Races, she’s also a National Sailing, America’s Cup and State of Michigan Hall of Fame inductee. Oakcliff offers an innovative environment that infuses sailors with a culture and drive for success.
ELEVATE YOUR GAME
RESULTS DELIVERED
Oakcliff‘s 700+ graduates form an extensive alumni network and pull fellow trainees into marine industry jobs and race programs around the world, kickstarting careers. Graduates have won The Ocean Race, brought home the Bronze and raced in Barcelona.
Results begin before graduation. Oakcliff trainees and coaches won the Herman Hawkins and Youth Trophy in the 2024 Newport to Bermuda race. Past wins include the Miami to Havana Race, NYYC Annual Regatta and the Opera House Cup, with podium finishes in past Bermuda, Around Block Island and Vineyard Races. Teams made up entirely of trainees and coaches hold course records for The Around Long Island Race (2018) and the Bayview Mackinac Shore Course (2021).
I joined Oakcliff for exposure to the sailing world and three years later I was designing America’s Cup boats.”
— ROBYN LESH, Sapling Graduate, American Magic Design Team
Want to step up and become a professional sailor, waterfront director, top coach, or start your own company? This is your next step. Considering starting an Olympic Campaign, or are you a club sailor who wants to win a national championship? Most importantly are you willing to work hard, have fun, and be curious? You are a fit for Oakcliff.
ARE YOU READY FOR OAKCLIFF?
Graduates from Oakcliff have gone on to do incredible things: Seth Cooley, Chief Engineer at Future Fibres; Madeline Gill, North Sails designer and Ervin Grove co-owner North Sails Charleston. Oakcliff sailors went to the Olympics and brought home medals. 15 sailors and designers were hired by American Magic and increasingly they are working in the technology and defense industry, including Hunter Stires, Maritime Strategist to the Secretary of the Navy.
ACHIEVING DREAMS
SAPLING PROGRAM
A summer-long dive into the world of professional sailing at Oakcliff’s America’s Cup style campus. The Sapling program is a dynamic apprenticeship program making every single day different than the next.
LEADERSHIP
Get first-hand experience as a boat captain, first mate, safety officer, navigator, fleet manager and more. You will also be put into coaching roles so you can solidify your knowledge, raise your confidence level, and learn to communicate effectively.
SPECIALIZED TRAINING
A rigorous training schedule is focused on skills from marine electronics, rigging, composites, marine engines and campaign management, all the way to physical fitness and high intensity strength training.
CONNECTIONS
Network and develop lasting relationships with sailors out on the race course and leaders in the industry.
INDUSTRY JOB PLACEMENT
Explore multiple career options in the sailing industry with Oakcliff’s coaches and partners providing an insider’s perspective. Nearly all graduates are employed or continuing their education. Most don’t want to leave. Many have transitioned to full-time Oakcliff team members.
ACORN PROGRAMS
MATCH RACING
As the first official Academy of the World Match Race Tour, sailors are coached by a roster of America’s Cup and Tour competitors. Sailors sharpen their skills through fierce match race drills and in two graded match race regattas. These new tools can be taken forward immediately, onto the Grand Slam Series.
Competitors hone their tactical skills but also play with sail shape, understand aerodynamic theory
and tune rigs. They also gain marketable skills such as winch and sail repair, and possibly most importantly, learn how to be a valuable team member and leader of a team.
OFFSHORE RACING
If sailing under the stars, being out of sight of land, and learning what it takes to propel your team to the finish of a distance race sounds enticing, this program is for you.
Trainees complete thousands of offshore miles sailing along the East Coast and racing across oceans. They progress from being a Safety Officer to Watch Captain, Mate and Boat Captain.
Master advanced navigation and gain a World Sailing Safety at Sea Certificate.
Industry tours and specialized workshops provided by leaders in the field will offer one-of-a-kind networking opportunities.
SHORT HANDED PROGRAM
This intense program provides advanced doublehanded offshore training. Along with boat prep, trainees will compete in overnight training with coaches at their side. Included is a World Sailing Safety at Sea Certificate. Trainees will compete in a 24 hour offshore race in retrofitted Melges 24s or Figaro 2s. Short Handed is the hardest discipline for a sailor to break into. This is one of few paths, along with the British Keelboat Academy and a professional program in France.
WINTER SAPLING: January 16 – May 6 and September 4
($3,500* per semester or $200 per week) Explore all aspects of the marine industry from hands-on technical training to project management. Be a part of the team, focus on fitness and plan your future.
USPA HIGH SCHOOL PROGRAM: January 16 – May September 4 – December 15 ($20,346*) Take fully accredited High School classes through USPA while training full time at Oakcliff.
WINTER SUMMER TRAINING
SAPLING PROGRAM: May 1 – September 4 ($950 per week*) tons of Offshore, High Performance, and Match Racing. The ultimate apprenticeship and job training. Chart your career in the marine industry to go Pro or even join the Oakcliff staff.
HIGH PERFORMANCE: Weekly ($2,300 Per Week/Camp*) Train on 49er, FX, Nacra, ILCA, 470 & Waszps. Camps lead into Triple Crown Regattas; win prize-grants for future training costs. Boat usage for connected Triple Crown Regattas included. HP Camp Dates: June 11-17, July 14-22 (470 only), Aug 9 -12. June dates are just after college nationals and before summer really begins. Private coaching on demand.
WORLD MATCH RACING TOUR
ACADEMY: July 8 – July 22 ($1,900*) The Academy is back with two weeks of Match 40 Racing. Receive expert coaching from match racing legends, race in an Oakcliff Grade 4 & Grade 3. Come from the Gov Cup, train and head onto the Grand Slam Series a part of the WMRT.
FOR MORE INFORMATION: training@oakcliffsailing.org , 516-802-0368, Oakcliffsailing.org
Need based scholarships available for all programs, *All programs include room and some board.
OFFSHORE
AYC SPRING: April 26 – 27 May 2 – 4 ($400*) Spring Training! Back-to-back weekends including racing AYC Spring on a Turboed Farr 40. Get-on-the-water coaching with quality debriefs before most of your competition’s boats even get wet.
DOUBLEHANDED OFFSHORE: May 4 – 10 ($1,225*) With Double-handed Olympics on the horizon, now is the time to train. Race one design confidently, with Oakcliff’s Offshore Modified Melges 24s and extensive safety protocols.
OFFSHORE I AROUND BLOCK ISLAND: May 16 – 27 ($1,225*) This program is for all levels of offshore racers and a qualifier to race the Newport to Bermuda Race ‘25. Includes the Around Block Island Race and International Safety at Sea training.
OFFSHORE I & II ANNAPOLIS TO NEWPORT: May 16 – June 12 ($2,175*) Get Maximum Miles. Race one-design in our fleet of Turboed Farr 40s. Learn from industry pros and become a safe, accomplished blue water sailor. This program includes Safety at Sea Certification.
OFFSHORE III MARBLEHEAD TO HALIFAX: July 1 – 17 ($2,175*) Race from Marblehead to Halifax, Canada. Pair this with the Chicago Mac or Annapolis to Newport to get over 2,000nm of offshore sailing.
MIDWEST I BYC MAC: July 6 – 17 ($1,225*) Learn what it takes to get a boat offshore ready and compete in one of the fresh water greats, the Bayview Mackinac Race, on OC68. Start in Michigan & finish in Chicago.
MIDWEST II CHICAGO MAC: July 15 – 29 ($1,225*) Race the 150th Chicago Mackinac. Join in Mackinac, deliver, race & deliver for a total of 900 sea miles.
VINEYARD TEAM-TRAINING: August 26 – September 2 ($950*) Did Summer get away for your team? This program is a quick trip into offshore racing. Bring a team and let our coaches guide you from start to finish.
HIGH PERFORMANCE
Our High Performance program is where Olympic Campaigns begin. It is also an excellent way for high school dinghy sailors to train for college. Whatever your goals are, we can help you achieve.
We have six foiling Nacra 17s, two carbon Nacra 20s, nine 49ers, nine 49er FXs, ILCAS, 470s and six foiling WASZPs.
TRIPLE CROWN REGATTAS
Support US Olympic hopefuls, awarding up to $500,000 in prize grants each year.
FOILING CAMP
Foiling Camp is back and our fleet of WASZPs, Foiling Nacra 17s, and 20s will get you up and flying. Expert coaches will provide personalized advice on how to take your fitness to the next level and earn your wings at Oakcliff Airlines.
OUR BASE
The Oakcliff campus is modeled after an America’s Cup facility. We do virtually all maintenance in-house, including sail repair, rigging, splicing, painting, composites and engine work. Between our sail loft, machine shop, painting, and rigging departments, there is nothing we can’t tackle.
Local trainers and coaches customize rigorous fitness sessions for athletes. After a long day on the water, sailors and competitors can relax in our modern bunkhouse.
Want to get ahead? Private foiling and coaching on the HP boats available upon request.
Every year over 1000 national and international athletes stay at our bunkhouse while competing and training at Oakcliff.
OUR ACCOMMODATIONS INCLUDE:
• Air-conditioned living quarters
• Private Showers and Laundry Facilities
• Multi-media debriefing space
• Gourmet Kitchen and Pantry
• NOT INCLUDED: Maid service
HIGH PERFORMANCE HIGH
SCHOOL
Take fully accredited classes while sailing. Oakcliff has partnered with the US Performance Academy to bring high school classes to Oakcliff’s campus and created the High Performance High School. Trainees 15 and up take accredited, online high school classes through USPA and get the bonus of time on the water after completing their day’s work. Students can choose from a number of courses and electives from USPA, including AP courses.
Much like the weather, the Oakcliff/USPA schedule is flexible. With USPA’s online system, we are able to plan for school work-intensive weeks and sailing intensive weeks. Students have opportunities to travel for sailing, such as skiff training in Alabama, racing at Charleston Race Week, and more. Students that are self-driven, motivated and organized thrive in Oakcliff’s training environment. To apply visit: oakcliffsailing.org/oakcliffs-highperformance-high-school
BE A SUPPORTER
Oakcliff is an inclusive organization that is open to all. Supporters are vital to the success of our programming. Your donation gives you access to a full year of sailing and social opportunities to race and train alongside the sailors you help sponsor.
AS A SUPPORTER JOIN US FOR:
• Regular match racing
• Coached fleet racing
• Shields sailing
• Race management training
• Offshore racing
• Clinics and seminars
• Fundraising parties
• Open sails & BBQ
Check out the online calendar to sign up for these unique opportunities.
HELP US ELEVATE THE GAME
Your tax-deductible donations help to provide lifechanging experiences and need-based scholarships for athletes training at Oakcliff.
DONATE YOUR BOAT, CAR OR RV
Oakcliff is always looking to expand our programing. Donate a boat, or especially a vehicle, or RV.
SUPPORTER PERKS
Oakcliff is leading a renaissance in Oyster Bay. Sail by day and wander through town by night. Experience the rare opportunities Oakcliff has to offer through sailing, racing, learning, or relaxing with new friends and mentors.
DREAM TEAM COACHING
Connect and learn from established pros and coaches: Dawn Riley, Dave Perry, Dylan Whitcraft, Ralf Steitz, Jensi Linder, Chris Poole, Quantum Racing coaches including Grant “Fuzz” Spanake and Tom Burnham, and sailing legend, Gary Jobson.
INDUSTRY PARTNERS
Receive exclusive news and training from our partners: Gill, Regatta Craft Mixers, Harken Derm, Vesper Marine, Guzzle H2O, Stone Brewing Co., Interlux, Expedition, Selden Masts, Marlow Ropes, Spinlock, and Hobie Sunglasses.
To find out about more Supporter Perks visit our website at: Oakcliffsailing.org/supporter-corner
CHARTERS FOR RACING
Have a team? Need a boat? We have everything from offshore racing boats to Olympic class boats. Charters can include coaching opportunities to bring out the best in your team.
OUR GROWING FLEET
Our dynamic fleet of 100+ boats includes Foiling WASZPs, UFOs, Nacra 15 and 17s, 49ers, 49er Fxs, 470s, ILCAs, and Melges 24s, Big boats; JV 66 “Numbers”, RP86 “OC86”, “OC68”, Ker 50, 4 Farr 40s, Ker 11.3, Farr 11s and a Class 40. Most are actively for sale and more are donated yearly.
BUILDING TOMORR OW’S LEADERS
CORPORATE TEAM BUILDING
Effective and efficient communication is the cornerstone to a successful team. No other sport offers such an ideal platform for corporate and group training in risk analysis, problem solving and leadership. Bring your company and enjoy a custom-tailored event.
Photos by Stephen R. Cloutier, John Lincourt, Molly Riley, Peter Taylor, Ethan Johnson, Francis George Design by Danielle Gallo Creative
