City Island Yacht Club

Incorporated 1907

header image

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.

Come join us, whatever your skill level! 

2023 Regatta

Big Tom City Island Cup

Saturday, June 10 

Harlem Yacht Club is hosting this event. 

Register now for this first race of the season.



87th Annual City Island Yacht Club Distance Race  

Saturday, June 24  Start: 10am

Registration and Notice of Race:

42st Annual City Island Yacht Club Women Skippers Race

Saturday, August 12 Start: 1pm

Post-race reception with keg of beer and snacks

Registration and Notice of Race:

70th Annual City Island Yacht Club Day Race

Sunday, August 13  Start: 10am

This is the second race in the Western Long Island Sound Triple Crown which includes Port Washington YC Day Race on June 5 and Douglaston Yacht Squadron Captain Island Race on TBD. A boat must be in all three events to qualify. 

Registration and Notice of Race: 

2023 Governor’s Cup Charity Regatta

Saturday, August 19 

Registration and Notice of Race:


Saturday, September 23

First race starts at 11am. 

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

Registration for race and for buffet lunch: (please answer all questions/prompts)  Eventbrite

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

Chart: Sayers-Series-Chart2021



CIYC has also been instrumental in establishing and organizing these races:


2023 Racing Schedule

Big Tom Wednesday Night Series 

  • May 24 through August 23 (14 weeks) Start: 7pm
  • Registration:
  • Contact:

TGIF Sunset Series at CIYC 

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

Free, casual race. See dates below. Start: 7pm. Notice of race to come. 

  • June 9
  • June 23
  • July 7
  • July 21
  • August 4
  • August 18

Registration and info:

Sunday Jams 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. 

Datesates below: 

  • July 23
  • August 6
  • August 20
  • September 10

No windward–leeward courses and no spinnakers. Also, no poling out jibs or genoas with spinnaker poles or whisker poles. Non-racers and racers are encouraged to bring family members, sailors, and non-sailors. There will be a long start line with plenty of room for everyone to start. The start line will be between a white mark and the yellow flag on the Race Committee boat. You will not be able to miss it. The committee boat will monitor VHF channel 71. Results will be announced on the CIYC porch after the race. Boats will be scored PHRF, time on distance, and racing boats will be scored separately from cruising boats. If you don’t have a PHRF certificate, we’ll figure out what your rating should be. There is no entry fee. If there is a NOAA small craft advisory in effect as of 10:00 a.m. on the day of the race, the race will not be held. If you want to come out, contact Jim Dennis at or 914-714-2195.  I2023