Racing & Regattas

The CYC Foundation supports the Rickover Academy JNROTC racing team, the Neill Advanced Sailing Clinic for accomplished junior 420 sailors, and the North American Challenge Cup, one of the longest-running sailing events for disabled adults.

Rickover Academy

To promote the nautical arts, the Foundation began a sail safety and training program with the Rickover Naval Academy in 2008. Rickover is one of several military academies in the Chicago Public School system and is located within Senn Public High School in the Edgewater community. 


The Rickover Racing Sail Program follows a strong format of consistent curriculum, instruction and scheduling. Through a partnership, CYC Foundation supports the Rickover Academy JNROTC racing team by supplying safety equipment, sail training and transportation.

There are two distinct teams within this program. The Development Team teaches beginning and intermediate sailing to the cadets. If Development Team members progress and want to move to the next level, they are promoted to the Race Team. They learn advanced sailing techniques and racing tactics that they apply on the race course against other Midwest high school teams. With this structure, the cadets are able to mingle with students from other high schools and go back to their school with unique experiences and expanded horizons.

Neill Advanced Sailing Clinic

The Neill Advanced Sailing Clinic, sponsored by the CYC Foundation, is a high-level educational opportunity for the country’s most accomplished junior 420 sailors who are working hard to elevate their racing skills to the next level. The clinic is named for Tom Neil, who was an avid Chicago Yacht Club sailor and competitor locally and nationally. 

The program consists of lectures and on-the-water drills including tactics, strategy, sail trim and boat speed. Coaches use daily video footage, archival footage, chalk talks, land demos and on the water exercises. The experience is rounded out with nightly guest speakers, presentations, and Chicago sight-seeing to show the sailors new avenues of sailing and a little of the amazing city of Chicago.

More information and applications are available at neilladvancedsailingclinic.com.

North American Challenge Cup

In 1992 the Chicago Yacht Club created the North American Challenge Cup as a major disabled sailing regatta, bringing together disabled sailors from around the country. This event counts as one of the longest running events in the North American disabled sailing circuit. The NACC has a reputation for outstanding competition on a national and international level.