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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  • Summer Sailing Students
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  • Get ready for the ultimate adventure!
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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.

SwimSailScience (SSS) is a no-cost, fun, three-week program for Boston Public School students going into grades 4, 5, and 6 who are identified at being at risk of summer learning loss and who can most benefit from summer programming. The program participants are from low-income neighborhoods, have behavior and/or learning disabilities, have emotional issues, and are disadvantaged. During our program we provide students with three hours of sailing lessons, one hour of swimming lessons and one hour of hands-on, engaging science lessons. The students who attend also receive transportation to and from the sailing center, breakfast, lunch, and reusable water bottles all at no cost.

Work with SSS Head Sailing Coach and SSS Science Teacher to organize SSS students
Oversee SSS Leaders
Manage up to 30 students, with assistance from SSS Leaders, SSS Head Sailing Coach, and SSS Science Teacher
Disseminate evaluation surveys at the beginning and end of each session
Complete a Massachusetts Work Based Learning Plan for each of your instructors, leaders, SSS Head Sailing Coach, and SSS Science Teacher
Communicate with the parent's of your sailing students regarding what students need to bring each day and how each student progressed
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

2-3 years of teaching experience
2-3 years of team management
At least 2 years of sailing instruction
Current First Aid/CPR certification
Positive and enthusiastic attitude
Outstanding communication and team management skills
Excellent references
A passion for sailing, the ocean, and working with kids