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 the opportunity to join us for Wednesday night fleet racing, in conjunction with Sagamore Yacht Club. You can also come out on Friday afternoons for coached Supporter Sailing sessions. 

On Wednesday nights enjoy on-the-water coaching, our own start, and a competitive fleet, sailing either a Swedish Match 40 or a Shields. This is a great way to improve your skills between regattas. Enjoy post-race debriefing at Cooper’s Bluff, Sagamore, or any other fine Oyster Bay establishment.

During Supporter Sails,  you can sign up to sail one of our Lasers, Shields, or Sunfish on Fridays starting at 2pm. At 4:30pm we will break out and run races for those interested.

Once back on dry land, join us back at Oakcliff and enjoy our NEW BBQ; this is an excellent way to kick off your weekend and get the party started!

Become a Supporter today 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 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.

Shields RACING

Oakcliff races our historic fleet beautifully kept Shields. The Shields fleet can be sailed on select Fridays with the opportunity to join racing at 4:30 along with other classic yachts from the Stirling Harbor Foundation.