Step 6: Instructors-in-Training

Through this 7-week 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
6/25 – 8/13 7 weeks
*no class July 4
Daily schedule:
8:45am – 3:30pm
Instructor-in-Training Job Description
Apply today

For New Applicants to the IIT program:

The 2018 Instructor-in-Training (IIT) application is available until March 15th. Based on applications, a select group will be called back for an in-person interview and sailing test. Acceptance decisions will be made no later than April 1.

Applicant requirements:

To be accepted into the 2018 IIT program, you must:

  • Be 15 years old before July 1, 2018
  • Have successfully completed a full session of Step 5 in 2017, or its equivalent *
  • 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
  • Ace 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 immediately; as this may not necessarily 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, 2018, you hurt your chances of being rehired. For those to wish to be rehired, an interview and sailing skills test may be conducted later in the spring, exact process and dates TBD.

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.


Ashton Smith
Director of Youth Programs and Outreach
(857) 452-1763