Racing For All

Oakcliff has more match racing than anywhere else in the US, but it doesn’t stop there.  We also coach fleet racing in Oyster Bay and send teams across oceans in offshore events.  If it is relaxed and beautiful sailing you’re interested in come and race on a classic.  Scroll down to learn more about each of our fleets. Check out our calendar for information on specific regattas and clinics and to register. From the start of spring to the end of fall, things at Oakcliff Sailing are pretty busy!

Match RacingOakcliff Match Racing

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.

  • Drills
    Tuesday evenings in the spring, summer and fall, Oakcliff supporters take to the water in Match 40s for practice drills. We work on sets, douses,  dial ups and mark roundings, and run drills like lead/push,  penalty clearing, time on distance and much more. With intense on-the-water coaching and umpiring, everyone ups their game.
  • Clinics
    Combine some of the best match racers from around the country,  the largest fleet of  Match 40s in the world and top-tier visiting coaches and you have one superb learning opportunity.
  • Regattas
    Oakcliff is the biggest Match Racing center in the USA, organizing multiple events from Grades 5 to 2 throughout the season.
  • Seminars
    Oakcliff offers seminars for umpires, race officials and judges for those who wish to become certified or simply want to learn.

Shields-@-mark1Fleet Racing

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

On Wednesday nights you can join our Match 40 fleet race series. Oakcliff Supporters who race at least 5 Wednesdays  receive a 5% discount on a Dream Yacht Charter over the winter.  Form and sail as a team of 3 or more 5 times to receive an additional 5% (chartering as a group). If you are a member of US Sailing you can pile up an additional 5% discount. Get better quicker with regular coaching and build up your boat handling skills.

Oakcliff Offshore Racing

Offshore Racing

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

Our classic yachts were hot racing vessels in their heyday. One look at them today evokes the beauty of sailing. At Oakcliff they are  raced every week. Throughout the spring and fall they join up to 20 other classic yachts filling Oyster Bay with their graceful presence every weekend.  Thursday evenings all summer long the classics sail the same course while the setting sun glistens on time-worn but exquisitely restored wood.

Dolphin is a Herreshoff design, a Newport 29. She was launched in 1914 and is 35’7” overall and 29’ on the waterline. She raced successfully for many years, including three years in the Mediterranean, sailing in the classics regattas of Mallorca, Menorca, Imperia, Cannes and St. Tropez.

Nautilus, the oldest classic in the fleet, was built in Bristol, Rhode Island in 1905, also by the Herreshoff Manufacturing Company. She is a NY30 design, gaff-rigged, with an overall length of 43’ and a waterline of 30’.

Oriole II is a 30 square Metre racing yacht designed by Herreshoff and built by one of the finest boat builders in the world, Lawley & Sons.  She is an open cockpit racer, with a dramatic swept-back mast, small jib and very large mainsail.  She has a full keel, with lead ballast, the decks are canvas and epoxy.  The bottom is a white oak keel with lead ballast attached by bronze bolts