Employment Information

Interested in a challenging, yet fun and rewarding summer job? Longshore Sailing School has a variety of job openings each summer. To apply, download a copy of our application (pdf or doc) and return to:

Longshore Sailing School
Attn: Operations Manager
Longshore Club Park
260 Compo Road South
Westport, CT 06880

Personal interviews are required for all applicants.

Minimum Qualifications


  • Must be at least age 18;
  • Have a Connecticut Safe Boating Certification;
  • Have a strong background in sailing; and
  • Have both First Aid and CPR Certification*.

Jr. Instructors

 must have the same qualifications as the above* but may be a high school senior over age 16.


  • Must be at least age 16;
  • Be reasonably strong and in good physical condition;
  • Have taken Advanced Sailing at Longshore or have had similar sailing experience; and
  • Have both First Aid and CPR Certification*.

*In-house CPR and First Aid training is conducted at Longshore in June.


There are a variety of pay grades. Pay varies according to rank and experience. Everyone works a five day week, including a number of weekends. The hours are often long, but the rewards can be generous if you are fully committed. The starting and ending dates of your summer employment can be somewhat flexible. Please be prepared to discuss this at your interview.

Team Photo, Summer 2016
Team Photo, Summer 2015