News

All four of the Olympic classes that competed in Stage 2 of the Oakcliff Triple Crown Series, make their way downwind (49er, Nacra 17, 470W, and 470M) OYSTER BAY, NEW YORK (September 30, 2019) - The Oakcliff Triple Crown Series has been running for three years...

Newport, R.I. (September 22, 2019) – Sailors with disabilities who have been racing in the fourth Clagett/Oakcliff Match Racing Clinic and Regatta have sailed for two days in Oyster Bay, N.Y. and there is a new team crowned the winners, Sarah Everhart Skeels (Little Compton,...

The 2019 Vineyard Race hosted by Stamford Yacht Club started in 15 knots of breeze gusting 18 with sunny skies. It was a downwind run off the line and all three Farr 40s deployed their A2s. They each also set a staysail for extra stability and a little...

OYSTER BAY, NEW YORK (August 11, 2019) - After two days of coaching by Volvo Ocean Race sailor and World Match Racing Tour Skipper, Nicolai Sehested, Oakcliff’s August Grade 3 Clinegatta pitted eight skippers against each other, three of whom were ranked within one point...

Join Oakcliff for a once in a lifetime opportunity to meander through a private and beautifully restored meadow on Centre Island. Along the way discover art  placed just for this event and enjoy light refreshments. Learn more about the show and buy your ticket here 2019...

Oakcliff's July Grade 5 saw medium breeze and a heat index of 110 and the racing was just as hot as the weather. With marked improvement in each of the five teams who participated, the racing got tighter and tighter as the day went...

Exercising at Peak 180 when he was still at Oakcliff Last October, Oakcliff collaborated with New York Yacht Club American Magic, Challenger for the 36th America’s Cup, to host a week of training & tryouts with Oakcliff graduates. Sean O’Halloran stood out amongst the candidates.  When...

Just like any sport, sailing is evolving quickly with modern technology. With heavier loads, lighter weight, and optimized designs, the boats are faster, more agile, and inherently more dangerous. As the industry shifts from displacement boats to planing and even foiling boats, crew fitness and...

 A little over a year ago, Sara Stone left her career in infectious disease control to become a Sapling at Oakcliff and pursue her dream of doing the Ocean Race. Since graduating from the program, her career has been pedal to the metal; just last week she did bow...