City Island Yacht Club

Incorporated 1907

Big Tom Yacht Racing Wednesday Night Series

City Island YC along with our partnered neighboring club, the Harlem YC, established Big Tom Yacht Racing (BTYR) in 2020 in an effort to encourage the growth of yacht racing on Eastchester Bay.  The organization, named for a pesky submerged rock on the Southern end of City Island has, to date, been rewarded by a steady annual increase in the number of competitors.  The Big Tom organization’s goal is simple. We work hard to create well-organized, fun, friendly, inclusive sailboat races for all types of sailors, from serious racers, casual cruisers, and their crews. 

BTYR oversees the Big Tom Wednesday Night Series (overseen by City Island Yacht Club) and the Annual Big Tom City Island Cup (overseen by Harlem Yacht Club).

The Wednesday night series, from May 24, 2023 to Sept. 6, 2023 offers a refreshing midweek opportunity to get out on the water and compete.  

❖ 16 weekly sizzling summer evening sailing races
❖ Top-notch sailboat racing in the vicinity of Buoy R-2 “Big Tom”, off City Island
❖ Challenging around-the-buoys courses for all kinds of boats and
all levels of sailing skill — experienced racer to beginner
❖ PHRF, SPINNAKER and NON-SPINNAKER classes, and ONE-DESIGN (minimum of 5 registered boats in a one-design class)
❖ Windward, leeward, and triangular courses.

Harlem Yacht Club runs the Big Tom City Island Cup series on the weekend of June 10, 2023. The City Island Cup is a qualifying race for YRALIS trophies.

Sign up now below for Big Tom Yacht Racing events on 

Following the sailing season the Big Tom organization celebrates the season with an annual gala awards brunch and party.

For questions or more info, email .
For official NOTICE OF RACE and registration information, go to

Download the info sheet: Big Tom Yacht Racing 2023

Big Tom Yacht Racing and Seawanaka Corinthian YC are winners of the YRALIS Arthur P. David Beach Point YC Trophy for yachting achievement on Long Island Sound by a member club.


Big Tom Yacht Racing News

Introduction to Racing Workshop

The City Island Yacht Club (CIYC) Racing Committee is excited to present a seminar to help sailors who want to ...

Sail Better with Better Trim – Bill Gladstone

Here’s a chance to master the "force", learn some new strategies from the Jedi Master of sailing, Bill Gladstone himself.  ...

Big Tom Yacht Racing Honored

CIYC’s Big Tom Wednesday Night Series and Harlem YC’s Big Tom City Island Cup events were honored at the 2021 ...