City Island Yacht Club

Incorporated 1907

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Committee boat, "Robin's Nest" sets the course.

Committee boat, “Robin’s Nest” sets the course.

Damon Runyon, the man who wrote the hard-boiled newspaper stories that inspired the musical Guys and Dolls, reportedly once went to view an America’s Cup race off Newport, RI. Runyon was not impressed. “Watching an America’s Cup race,” he wrote, “is like watching grass grow.” But anyone who has raced sailboats knows exactly the opposite. Racing is all at once exciting, skillful and at times a white-knuckle experience…of course, that’s if you’re doing it right!

At City Island Yacht Club we do it right.

The City Island Yacht Club hosted its first race in 1911, and continues a tradition of hosting well-run regattas… Our summer season on the Sound is full of opportunities to get out on the water and compete at all levels. Our big events each year are The CIYC Distance Race to Stratford Shoal, the Women Skippers Race in which a woman must be at the helm for the duration and the Annual Day Race around selected government marks in the Western end of Long Island Sound. In 2015 CIYC partnered up with two other clubs on the sound and hosted the first annual Western Long Island Sound Governor’s Cup Regatta. We’ll be hosting that event again in 2021. Each September everyone loves our annual, always fun Sayers Series ( for CIYC members only). It’s morning and afternoon racing with a luncheon in the middle.


City Island Yacht Club is an active member of the Yacht Racing Association of Long Island Sound (YRALIS) the organized racing authority that schedules other yachting events that can keep a skipper and crew busy pretty much from April until November. The CIYC is also the club host of the BIG TOM (fondly named for a notorious submerged rock at the southwestern tip of City Island) Wednesday Night Race Series, a wonderful mid-week excuse to get out on the water and sail in friendly competition . As a member of the YRALIS since 1914 our Club offers one of the most vibrant racing programs on the Sound today. In the past we’ve hosted national events such as the J/29 North Americans and Leukemia Cup Regatta. For those who like their racing at a more relaxed, though equally exciting, pace we offer a summertime Friday night series as well as a weekend JAM series (jib and main only) that attract lots of boats.

There’s even racing available for the non-boat owner! Many of the boat-owning skippers who race on Long Island Sound are always looking for fresh “rail meat” and developmental sailing talent. If you are looking to crew or a skipper looking for crew, contact us at the Club – With so many members involved in racing, there’s always a need to pair skippers and crew.

There’s so much sailing to be done this year and we at CIYC are honored to continue the Club’s long-standing traditions… Please come sail with us, we do it right!

Sailing News & Events

Commodore’s Update (July 3, 2020)

Dear Friends, This weekend, the weather is expected to be exceptionally fine. Celebrate July 4th with expanded al fresco dining on our porch and lawn ...
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Big Tom Yacht Racing is the New Version of a Classic Weeknight Sailboat Racing Event…

At the westernmost end of Long Island Sound, the Big Tom Wednesday Night Series offers 16 weekly sizzling summer evening sailing races beginning May 20, ...
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Sayers Series 2019 Results

Sayers Series Race – Henry Sayers Commodore of CIYC 1926-1927 raced Water Witch, a John Rodstrom schooner yacht and this CIYC Members Only race is ...
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Sunday JAM Results August 18, 2019

The final JAM of the season was raced in a 10-15 knot southerly, and the race concluded before any thunderstorms rolled through. The results are: ...
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TGIF Race Results #3, #4, and Season Scoring

July 19, 2019 TGIF Race Results #3 Weather: SW 8 kts Course: A - L - B - Finish Sail Number Boat Name Elapsed Time ...
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