Oakcliff may be known for running some of the premier match racing events in the country, but it encompasses that and much more: a US Sailing Team Olympic training site, hub for classic yacht sailing, and offshore training ground. Join us for all types of racing under the sun: fleet, match, offshore, classic, and high performance. 

Check out our calendar for more information on regattas, clinics, and event registrations. 

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Supporter Sailing

As a supporter, you have to opportunity to join us for Wednesday night fleet racing in conjunction with Sagamore Yacht Club or come out on Friday and Saturday afternoons for coached Supporter Sailing sessions. 

With on the water coaching, our own start, and a competitive fleet, Wednesday Night Racing is great way to improve your skills between regattas. Enjoy post race debriefing at Cooper’s Bluff, Sagamore, or any other fine oyster bay establishment. All boats in our fleet are available to race, but primarily we will be sailing our Swedish Match 40’s and Shields.

During Supporter Sails, Friday and Saturday from 12pm-5pm during the summer, Supporters can take out any boat from our Lasers to Classic Yachts, either for training or just for a casual sail with the family. Become a supporter and sign up on our Calendar to reserve your boat. 


As the most active match racing center in the world, Oakcliff’s twelve Match 40′s are used for drills, clinics and regattas. There is no quicker way to increase your boat handling, knowledge of the rules and ability to work with a team than in match racing. Nearly every weekend throughout the season, you can find graded match racing events on the bay, including the Oakcliff International.

With drills, clinics, seminars, and monthly regattas, Oakcliff is the best place for you to hone your match racing skills. Check out our regattas page for information and invites. 


Fleet racing takes place primarily in the fall and spring aboard our Kerr 50 and four turbo charged Farr 40s. These fleets compete in American Yacht Club and Manhasset Bay series.

On Wednesday nights, supporters can join our Match 40 fleet race series. Become a supporter and sign up on our calendar


Select supporters will have the opportunity to join Oakcliff for a variety of offshore races including the Newport-Bermuda Race, the Marblehead-Halifax Race, the Ida Lewis Distance Race, the Around Block Island Race, and the Around Long Island Race.  

Oakcliff boats are also available for sponsorship or charter for offshore sailing.  When a boat is sponsored, our experienced sailors supplement your team.

Classics RACING

Oakcliff races our fleet of beautifully kept and restored classic yachts. In the spring and fall, they compete with up to 20 other classic yachts in an Oyster Bay series. Oakcliff’s classics fleet includes two twin Newport 29s, Dolphin and Mischief; Herreshoff-designed Metre racing yacht Oriole II; and modern-classic Waterwitch

These yachts are also available for experienced supporters to take out on Fridays and Saturdays during our new Supporter Sails.