Racing For All

Oakcliff has more match racing than the Chicago Match Center 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!

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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 on Tuesdays. New for 2014, Oakcliff will run some Tuesday drills as Grade 5 event, giving mid-week skipper points.
  • 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. Every regatta at Oakcliff also has a clinic reflecting the Grade of the regatta (5 to 1) it precedes.
  • Regattas
    During the 2014 season, Oakcliff Sailing is scheduled to host 18 graded match racing events. Because of the clinic portion, these are coined ‘clinegattas’.  There are also specialty events like the Youth Clinegatta and US Women’s Match Racing Championship with clinic.
  • Seminars
    Finally, Oakcliff offers seminars for umpires, race officials,  judges for those who wish to become certified or simply want to learn. Please see our calendar for a full listing.

Shields-@-mark1Fleet Racing

It’s not all match racing at Oakcliff Sailing. We also provide fleet racing opportunities to our supporters. Fleet racing takes place primarily in the fall and spring aboard our six Melges 24s, three Ker-designed IRC boats and two Farr 40s  and a Farr 47. These fleets compete in American and Manhasset Bay series.

During the summer, we send our Match 40s to compete in Sagamore Yacht Club’s Wednesday evening racing, accompanied by an Oakcliff coach boat (with special permission from Sagamore). You’ll be amazed at how quickly you improve with regular coaching, and soon you’ll be joining us for Tuesday night match racing.

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Offshore Racing

For those interested in pursing offshore races or getting an idea of the endurance it takes to compete in a multi-day ocean race on our Farr 47, Kerr 50, Kerr 11.3 or Ker 11.5, Oakcliff is highly competitive in all of the offshore races we send sailors to. 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

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Our two classic yachts, Dolphin and Nautilus, 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’.