Sailing Instructor​/Swim Instructor

The Chicago Yacht Club Foundation is seeking sailing instructors and swim instructors for our Summer 2026 community outreach 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 and swimming, there are many chances for professional development in specialized focus areas (marketing, boat work, event planning, logistics coordination).

Our fleet includes J/100s and smaller keelboats, and runs from June 1st to August 14th, 2026.

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

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. Most 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.

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

End date:
August 14th

Pay: $16.60-25+, depending on experience

Mandatory Qualifications for SAILING instructors:

• 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

Mandatory Qualifications for SWIM instructors:

• Certified as a Swim Instructor or a Water Safety instructor
• CPR / First Aid / Safe Sport Certification
• Experience teaching kids who have no prior swimming experience
• Ability to pass a background check and fingerprinting

The Chicago Yacht Club Foundation is an equal-opportunity employer with a

commitment 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: (Use the "Apply for this Job" box below).

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