Summer Jobs @Courageous

We seek highly motivated, skilled sailing instructors and educators, those who will ensure that our students are safe, have fun, and have the optimal setting to grow and learn as blossoming sailors.

Each year, Courageous hires over 100 seasonal staff and instructors. Our instruction team is enthusiastic, energetic, and diverse, united by common passions for sailing, the ocean, and working with kids. They range in age and experience from high school and college sailors, to NOLS instructors, to tall ship crew and seasoned cruisers. We also hire experienced educators, naturalists, and outdoor educators who enhance our summer programs with their unique expertise.

Our staff members also enjoy a wide range of benefts, including: racing opportunities, professional development support, connection to the growing Courageous alumni network, and the satisfaction of having a job that makes a difference. Come spend your summer sharing your passion, making a difference, and being part of an exceptional team of instructors who are united by their dedication to the Courageous mission.

Available Positions

  • IIT Program Coordinator +

    DescriptionAt Courageous Sailing Center, we run an intensive Instructor in Training program for a diversified group of Boston teens ages 15-17. We have 22 students… Read More
  • IIT Beginner Head Coach +

    DescriptionAt Courageous Sailing Center, we run an intensive Instructor in Training program for a diversified group of Boston teens ages 15-17. We have 22 students… Read More
  • IIT Beginner Assistant Coach +

    DescriptionAt Courageous Sailing Center, we run an intensive Instructor in Training program for a diversified group of Boston teens ages 15-17. We have 22 students… Read More
  • IIT Advanced Head Coach +

    DescriptionAt Courageous Sailing Center, we run an intensive Instructor in Training program for a diversified group of Boston teens ages 15-17. We have 22 students… Read More
  • IIT Advanced Assistant Coach +

    DescriptionAt Courageous Sailing Center, we run an intensive Instructor in Training program for a diversified group of Boston teens ages 15-17. We have 22 students… Read More
  • IIT Intermediate Head Coach +

    DescriptionAt Courageous Sailing Center, we run an intensive Instructor in Training program for a diversified group of Boston teens ages 15-17. We have 22 students… Read More
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  • Get ready for the ultimate adventure!
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Complete our online job application.

[Note: Upload your resume and cover letter directly to this application.]

Application Resources


Contact Kate Henderson, Director of Youth Programs at kate@courageoussailing.org with any questions about applying.