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.

Click here for information on our Instructor-in-Training Program.

  • HS-sailing02
  • yp-smiling-kids
  • 64shore
  • yp-hands-on-learning
  • CourageousSailing05
  • CitSch2-a
  • ap-cruising-courses
  • Get ready for the ultimate adventure!
  • Rozalia Project at Courageous-21
  • yp-excited-boy-classes

Complete our 2015 online job application form.

[Upload resume & cover letter to this form.]

Application Resources

Contact Kate Henderson, Director of Youth Programs at with any questions about applying.

** please excuse our appearance while this site is under construction **

Charlestown Site Director

Job Description

[coming soon]

Attend all 3 days of staff orientation
Attend staff meetings
Be a team player
Maintain a fun, positive, friendly atmosphere for your students
Instill a sense of respect and safety for the Courageous fleet and for each person


[coming soon]