Instructors in Training

Through this 7-week paid summer job-training program, students make the transition from student to instructor, developing their abilities to teach, lead, and inspire the next generation of Courageous kids.



Under the guidance of our senior instruction team, participants first attend a one-week, pre-season training sessions and then participate in six weeks of intensive professional training, covering everything from teaching theory and classroom management, to long-distance cruising, safe powerboat operation, race committee administration, and boat maintenance.

Course Information

Dates Duration
June 24 – August 12 (no program July 4) 7 weeks
Daily schedule:
8:15am – 4:00pm
Instructor-in-Training Job Description
Apply today

For New Applicants to the IIT program:

The 2024 Instructor-in-Training (IIT) application will become available in January. Based on applications, applicants will be called back for an in-person interview and acceptance decisions will be made in early April at the latest.

Applicant requirements:

To be accepted into the 2024 IIT program, you must:

  • Be 15 years old before July 1, 2024
  • Have successfully completed a full session of Step 5 in 2023, or its equivalent *
  • Hold or be willing to obtain a current First/Aid CPR certification (Note: IITs are responsible for covering the cost of their own certification.)
  • Complete the online IIT application form and upload your resume, cover letter and application essay
  • Wow the Program Director in an interview
  • Be a competent, confident sailor. Applicants who have not completed Courageous’ Step 5 will be asked to do a sailing check out
  • Commit to the full 7-week program

*If you have not completed Step 5 and would still like to be considered for the Courageous IIT Program, please contact the Youth Program Director at immediately; this does not exclude you from becoming an IIT.

Returning IIT’s:

If you have successfully completed the first year of the IIT program and wish to return for another year, please email the Youth Program Director. If you do not notify her by March 1, 2024, you hurt your chances of being rehired. 

Teen Working Permit:

Note that if you are a minor working in the Commonwealth of Massachusetts, you must obtain a working permit before beginning a new job. Completing this application takes time, and will require signatures from your school, primary care physician, a parent/guardian and your new employer. Don’t try to apply last minute! Click here to start your application and here to find out more about Massachusetts regulations for teen workers.


Courageous Sailing YP Team
Admin Staff