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Seeking Sailing School and Club Instructors, Coaches, and Guides!

Island Sailing School & Club
Portland, OR Contractor
POSTED ON 8/25/2026
AVAILABLE BEFORE 10/24/2026

Thank you for your interest in teaching at Island Sailing!


If you are looking to learn more about joining our crew you’ve come to the right place! We are always looking for good USCG licensed and certified (ASA or US Sailing) sailing instructors to teach our many wonderful students here at Island Sailing - you'll be able to teach as much as you'd like!


  • We are seeking instructors for all levels of classes.
  • We have opportunities for captains to teach classes; work with clients in private coaching sessions; take new folks out for discovery sails; and more!
  • If you have racing experience we also have additional amazing opportunities available we would love to discuss with you!


About Us


Our mission is simple: we actively and consciously seek to continually be creating the best possible space for people to learn and get into sailing together with a great community of like minded members who together and individually can create and share their sailing experiences.


At Island Sailing our crew culture is of prime importance to us. Though we are one of the largest sailing operations in the Northwest, we are indeed a small, dynamic, and growing crew and developing, fostering, and maintaining a healthy, positive, and supportive environment for everyone involved is a core focus for us.


Island Sailing School is focused on the "academy model" in that we have lengthened our classes from the industry standard of two days to three sessions each and we hold those classes on weekends and during the week. We also have limited the number of students to three per boat which dramatically improves the experience for both our students and instructors.


As one of the oldest American Sailing Association accredited sailing schools we more than happy to work with you to become an ASA certified instructor if you haven't already been teaching ASA courses - we can guide and support you through the process of gaining those valuable certifications. Sailing experience and having your Coast Guard license is required.


How This Works


You’ll receive a confirmation email from us letting us know we’ve received your application. We will of course review your application right away and notify you quickly of the next steps in the process.


Just Some of What We Value at Island Sailing


  • We believe that seamanship should be at the heart of everything we do when out there on the water. We think of seamanship as much more than a list of do's and don'ts or specific skills - instead we see seamanship as an attitude of approach.
  • We believe that in teaching it is very important to be "the guide on the side" and not "the sage on the stage".
  • We believe that sailing is much much more than just a "sport" or a "hobby" - instead to us it is a lifelong passion and an incredibly empowering pursuit that we love to share.
  • We believe that sharing our passion with others to help them become and grow as sailors is one of the most rewarding things we can do.


What You’ll Love About Us


  • We believe that culture matters! We focus on and work diligently to ensure a continuing process of creating, fostering, improving and maintaining the best possible company culture - and you will be part of helping us make that happen.
  • We believe that supporting our instructors in everyway we can is critical.
  • We will support you as a captain and instructor and we never pressure our instructors to certify someone even if they feel the individual may need more coaching.
  • We will support you if you have the skills, experience, and licensing to teach in other areas of the world - if this interests you let's talk!
  • We will happily work with you to allow you access to our fleet for your personal enjoyment should you currently not own a sailboat of your own.


Thank you very much for taking the time to consider these opportunities and possibilities and we look very much forward to talking with you!


We Are An Equal Opportunity Employer.

Because we value our crew, our culture, and our clients, we require that all candidates that receive and accept employment offers complete a background check as part of the hiring process.


Salary : $20 - $40

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