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.

Step 1 is a Basic Sailing 101 course offered to children ages 8 and up in the Greater Boston Area. Each student attends Step 1 for one week. During this time, they are introduced to sailing theory and gain sailing experience in Boston Harbor.
Step 2 is a Beginner Sailing course for three weeks and at the end, if they have progressed enough, the students can get tested to move up to Step 3.

Assist the Step 1 & 2 Leader in creating lesson plans for each week
Assist the Step 1 & 2 Leader in creating sail plans each day that you share with the site director
Prepare lessons for days when sailing is not possible
Facilitate chalk talks for students
Over see Step 1 & 2 instructors as they give chalk talks and instruction
Test students who are ready for Step 3
Do chores at the end of each day
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

US Sailing Level 1 Instructor Certification, equivalent or more advanced
2-3 years sailing instruction experience
Completion of NASBLA-approved safety boat course through the MA Environmental Police and/or through the US Sailing Level I certification course
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