Sailing Instructor​/Swim Instructor

Overview

The Chicago Yacht Club Foundation is seeking sailing instructors and swim instructors for our Summer 2026 community outreach program. The program provides first‑time learning opportunities at Chicago’s waterfront, with the fleet including J/100s and smaller keelboats. The role runs from June 1st to August 14th, 2026.

• Teach sailing and swimming to youth ages 10‑18, using a Social‑Emotional Learning approach.

• Create a fun and safe learning environment for participants from under‑represented communities.

• Skipper keelboats (J/100, Sonar, Colgate 26, Capri 22), including solo docking and mooring while instructing.

• Operate a powerboat when needed.

• Mentor students in specialized focus areas such as marketing, boat work, event planning, and logistics coordination.

• Basic Keelboat Instructor Certification OR Level 1 US Sailing Small Boat Instructor Certification or international equivalent (expense partially reimbursed by the Foundation)
• CPR / First Aid / Safe Sport Certification
• Experience teaching kids who have no prior sailing experience
• Background check and fingerprinting clearance

• Maintain a fun and safe learning environment; teach basic principles of sailing to a variety of learning styles and ages 10‑18
• Confidently skipper keelboats (J/100, Sonar, Colgate 26, Capri 22), including solo docking and mooring while instructing children on board
• Operate a powerboat when needed

• 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
• Background check and fingerprinting clearance

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

Pay: $16.60‑25+, depending on experience
End date:
August 14th.

To be considered, submit a resume and cover letter to (Use the "Apply for this Job" box below). you are bilingual or a certified swim instructor, please mention that in your application. Applications will be reviewed on a rolling basis; interviews will begin in December 2025.

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