Before founding Oakcliff Sailing Center, we looked at everything to do with sailing in Oyster Bay and around the world. Our research revealed there was a gap in the growth path of sailors, and that we had a very unique opportunity to fill that gap. The founders of the Center decided it should be dedicated to training sailors, boat workers, owners and teams in order to raise the level of sailors and sailing in the United States. Out of dedication to that goal, the Acorn program was born.
The Acorn program is Oakcliff Sailing Center’s signature offering. With scholarships offered to individuals between the age of 18 and 30, it is open to anyone who has shown potential as a racing sailor. Acorns are completely immersed in the world of competitive sailing: everything from the sponsorship and business side of sailing to high–level match racing skills, from proper wet sanding and team management to basics in budgeting and accounting. Graduating Acorns are fully prepared to manage race boats, sail in the America’s Cup, or start businesses. At Oakcliff we see Acorns as the people who will carry our mission forward, representing Oakcliff, its supporters, and America in the world of competitive sailing.
Oakcliff Sailing Center offers a variety of support options, tailored to your interest level and budget. From full sponsorship of an Acorn scholarship to a one-time cash donation of any size, we are grateful for your support of our mission to raise the quality of sailors and sailing in the US. We can’t do it without you.
We appreciate help from all our supporters when it’s time to get the boats in an out of the water. You’ll help our Acorns, Saplings, and Oakcliff staff, who are on-site doing the day-to-day work while learning valuable life, business, and work skills.
All levels of commitment come with the benefit of being able to sail OSC boats on certain race days.
We want everyone. If you have housemates, children, cousins, pets, or anyone else that wants in on the action, bring them!
Oakcliff is here to help you take the next step in your sailing career.
CAPTAIN'S TABLE SUPPORTER ($10,00 – $49,999)
If you go above and beyond for us, we promise to return the favor.
If you have an idea and want to see how Oakcliff can help, give us a call at and we’ll be happy to discuss a custom arrangement.
SUSTAINING CIRCLE SUPPORTER ($50,000 AND UP)
A select few will join our inner circle, enjoy the best that Oakcliff has to offer, and help clear our way forward through sustaining support. Please call us (516) 802-0368.