Sailing Instructor

At the Shore and Country Club, located in Norwalk, CT, we believe that teaching is the ultimate way to give back to the sport. With our Junior Sailing Program, our goal is to bring together the passion for wind and sea to create an enriching and memorable experience to our junior sailors.

We are looking for an experienced and committed sailor to join our team as a Junior Sailing Instructor for the 2026 summer season!

As a Junior Sailing Instructor, you will work to provide a safe, fun, and supportive environment for members to learn to sail; and develop the skills of already proficient sailors in both recreational and competitive sailing.

Head Sailing Instructor and Sailing Director

The Sailing Instructor position is full-time for 8 weeks.

Mid-June to mid-August 2026

Daily meals are provided.

The junior program has a fleet of Optis, Feva's and 420's. Sailors in the program will range from 8 to 17 years and is mid-sized with 40‑60 students.

$18 to $24 per hour, based on experience.

• Carries out daily start-up and close-down operations (e.g. rigging, clean up, etc.). Ensures the dock and sailing shack are orderly and in ship-shape at the end of each sailing day.
• Performs in-season day-to-day operations:
• Provides sailing instruction, at all levels, both in the sailing program and private lessons as requested.
• Runs sessions and organizes fun events for sailors, including rainy-day events.
• Coordinates and attends regatta activities.
• Ensures upkeep and maintenance of boats. Inspects for damage on a regular basis. Makes minor repairs to the boats as directed by the Head Instructor and/or Sailing Director.
• Ensures the program is carried out in the safest possible manner, in compliance with the safety rules.
• Communicates and interacts with parents and sailors.
• Provides regular feedback to sailors using appropriate techniques to support learning and development.
• Provides daily feedback to Head Instructor regarding program achievements, safety concerns, or other issues.
• Supports Head Instructor and Sailing Director to ensure all required tasks are completed.
• Performs other appropriate tasks assigned by the Head Instructor and/or Sailing Director.

Sailing Instructors need to be excellent communicators and teachers who love being around children. Instructors need to have significant experience as a sailor and as a competitor. We want our instructors to have an infectious personality that can pass on their love of sailing to the beginner sailor and the seasoned veteran. Instructors must make safety a priority and lead by example.

Experience as an instructor is preferred.

• Competitive hourly wage with the opportunity for overtime.
• Seasonal work, 40 hours a week.
• Daily meals and uniforms.
• Great working environment and the ability to work with a dedicated team of individuals.
• On-going training.

• US Sailing Level 1 or Higher, Certification
• U.S. Powerboat Safe Handling Certification
• Current First Aid, CPR, & AED Certification

Must be able to frequently stand and walk, have good coordination and balance. Must be able to lift, carry, and move objects weighing at least 50 lbs. at shoulder height or above. Must be able to bend, kneel, crouch, reach, and balance on unstable or uneven surfaces.