Community Sailing Instructor

The Chicago Yacht Club Foundation is a 501(c)(3) public charity dedicated to introducing the joys of boating to Chicagoland youth. Our focus is on getting youth from underrepresented communities onto boats - usually for the first time. All of our participants come from the South and West Sides of Chicago. Many of our participants have little to no swimming experience, and this camp is their first introduction to activities on the water. The Foundation is in the process of expanding our programs to positively impact thousands of local youth. We currently operate with three J/100s and are in the process of acquiring two smaller keel boats with outboard motors as well. 

The Chicago Yacht Club Foundation is seeking sailing instructors and assistant instructors for the community outreach sailing program. We are not a traditional sailing school; we are a nonprofit outreach program that provides first-time learning opportunities at Chicago’s waterfront. In addition to teaching sailing, there are many chances for professional development in specialized focus areas (marketing, boat work, event planning, logistics coordination). 

The right candidate will have prior sailing experience, a passion for working with Chicago youth with an emphasis on Social Emotional Learning, and an energetic, positive attitude! There are a lot of opportunities for keelboat racing- with a CYCF team on the J/100s.

Benefits: Hourly with 1.5 OT possible during some weeks; housing stipend is negotiable

Start date: June 1st

End date: August 14th

Pay: $16.60-25+, depending on experience

About Our Camp:

Each week, we partner with a community organization, such as Boys & Girls Clubs, Girls Inc., and One Family Illinois, to introduce young people to sailing. We provide each participant with all necessary sailing gear, food, and transportation. Our locations are the Chicago Yacht Club’s Monroe Station, 31st Street Harbor, and Jackson Park Harbor. We are a learn-to-sail camp that runs 4-5 days a week with week-long sessions all summer. Hours are roughly 8 am to 4 pm, Monday through Friday. There is a mandatory staff orientation beginning June 1st, the week before camp begins. 

Mandatory Qualifications: 

• Basic Keelboat Instructor Certification or Level 1 US Sailing Small Boat Instructor Certification or International equivalent (this expense can be partially reimbursed by the CYC Foundation)
• CPR / First Aid / Safe Sport Certification 
• Experience teaching kids who have no prior sailing experience
• Ability to pass a background check and fingerprinting

Other requirements include, but are not limited to: 

• Ability to maintain a fun and safe learning environment; teach basic principles of sailing to a variety of learning styles and ages, ranging from 10-18
• Ability to confidently skipper keelboats (e.g. J/100, Sonar, Colgate 26, Capri 22), including solo docking and mooring while instructing kids on board
• Ability to operate a powerboat, when needed

The Chicago Yacht Club Foundation is an equal-opportunity employer committed to fostering an inclusive environment. Individuals of all genders, individuals from traditionally underrepresented populations, individuals with disabilities, and veterans are encouraged to apply. 

To be considered for this position, please submit a resume and cover letter. If you are bilingual or a certified swim instructor, please mention that in your application. Materials should be submitted via e-mail and be addressed to Caroline O'Malley, Community Sailing Manager, Chicago Yacht Club Foundation:

communitysailing@chicagoyachtclubfoundation.org

Applications will be reviewed on a rolling basis. Interviews will begin in December 2025.