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.

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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.

Courageous Sailing Center operates an extensive summer program for youth ages 8-18 at three different sites throughout the Boston area. At our main site on Pier 4 in Charlestown Navy Yard we have a five-step program that takes students from basic classes through instructors in training (IIT) as well as two programs that provide free sailing and science programming to Boston Public School students. We are also looking for instructors at our Jamaica Pond and Camp Harbor View sites. Our instructors are skilled sailors who act as role models and function well as a team. Please find the descriptions of each step and other summer programs on our website, all for which we are hiring sailing instructors.

Sail in boat with students
Have students assist with sailing the boat
Teach sailing safety
Follow directions given from your step leader
Attend all 4 days of staff orientation
Attend staff meetings
Be a cooperative member of the Youth Program Staff
Maintain a fun, positive, friendly atmosphere for your students
Instill a sense of respect and safety for the Courageous fleet, Boston Harbor, and for each person

Exceptional sailing ability
Current First Aid/CPR certification
At least one year of sailing instructor experience for Step 1, SLP, and SSS
At least two years of sailing instructor experience for Steps 2 and 3
Positive and enthusiastic attitude
Outstanding communication and team management skills
Excellent references
A passion for sailing, the ocean, and working with kids