City Island Yacht Club

Incorporated 1907

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Regattas and Racing

Since its first race in 1911, CIYC has been a leader in promoting yacht racing at the western end of Long Island Sound. Our goal is to create a fun, friendly and inclusive environment for racers of all abilities.  Partnering with other yacht clubs and organizations, we offer a wide variety of regattas that appeal to both the novice sailor as well as the seasoned racer. For the novice racer, sailboat racing is the quickest way to learn how to improve your sailing skills, and for experienced racers, the learning continues.

If you are intersted in racing as a crew member, reach out to Stu Markowitz , (914)414-0093 or fill out the crew registration form at the bottom of the page.

2024 Regatta

Big Tom Wednesday Night Series 

  • Practice race on May 15; Start 7pm. Registration for Practice Race
  • May 22 through September 4 (16 weeks) Start: 7pm
  • Registration:
  • Contact:

Big Tom City Island Cup

Saturday, June 8 

Harlem Yacht Club is hosting this event. 

Registration and Notice of Race:

88th Annual City Island Yacht Club Distance Race  

Saturday, June 15  Start: 10am

Registration and Notice of Race:

43rd Annual City Island Yacht Club Women Skippers Race

Saturday, August 10 Start: 1pm

Post-race reception with keg of beer and snacks

Registration and Notice of Race:

71st Annual City Island Yacht Club Day Race

Sunday, August 11  Start: 10am

This is the second race in the Western Long Island Sound Triple Crown which includes Port Washington YC Day Race on June 2nd and Douglaston Yacht Squadron Captain Island Race on Sept. 7th. A boat must be in all three events to qualify. 

Registration and Notice of Race: 

2024 Governor’s Cup Charity Regatta

Saturday, August 17 

Registration and Notice of Race:

TGIF Sunset Series at CIYC 

Casual race open to any CIYC and HYC sailor/sailboat. Awards and prizes, music, dancing and great food and drinks at The Galley. Come and chill out, have some fun with us after a hard week at work!

Entry fee $60 for the series.

June 7th through August 16th, biweekly. Start: 7pm. Notice of race to come. 

Registration and info:

Sunday JAM Series at CIYC

The City Island Yacht Club cordially invites all cruisers, day sailors, and racers alike, to come out for a series of relaxed Sunday jib and main races. The races will be short, approximately one hour, and the courses will be triangles. Free, casual race. No registration required. Start time is 4pm. 

2024 Dates: June 9, June 30, August 4, August 18, September 1

No windward–leeward courses and no spinnakers. Also, no poling out jibs or genoas with spinnaker poles or whisker poles. 



Sayers Series

Sayers Series

2024 Date TBA

First race starts at 11am. 

If your boat needs a PHRF rating, please contact Richie Coar at 917-370-7938.

Registration for race and for buffet lunch TBA closer to date. 

Racing instructions: Sayers-Series-Race-Instructions-2023

Chart: Sayers-Series-Chart2021

Crew Sign Up 

If you have questions, or are interested in crew opportunities, contact Stu Markowitz at 914.414.0093 or . Or, fill out the form below and we will match you with a skipper:


    Wednesday Nights Big Tom SeriesFriday Nights, TGIF Sunset SeriesSunday JAM RacesOther Races