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
  • 4465543972 77206e9434 o
  • ap-cruising-courses
  • IIT
  • yp-excited-boy-classes
  • 64shore
  • CitSch2-a
  • yp-teaching-learning-sailing
  • Rozalia Project at Courageous-21
  • yp-smiling-kids

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 4 combines racing 420's and cruising J-22's. Students are advanced sailors looking to gain experience in both racing and cruising. Each session is 3 weeks long and during this time students get to participate in regattas and overnight camping trips on the Boston Harbor Islands

Work with the Step 4 Leader and Cruising Coach to create a comprehensive 3 week lesson plan
Create a sail plan each day that you share with the site director
Prepare lessons for days when sailing is not possible
Work with the Step 4 Cruising Coach to integrate racing and cruising
Work with the Step 4 Cruising Coach to organize and prepare for camping trips and regattas
Work with racing coaches in the Boston area to organize regattas
Prepare students to participate in local, regional and national regattas
Facilitate chalk talks for students
Lead chores at the end of each day
Communicate with the parent's of your sailing students regarding what students need to bring each day and how each student is progressing
Complete a Massachusetts Work Based Learning Plan for each of your instructors
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
2-3 years of race coaching and experience in 420's
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