Courageous IIT Program 

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.


Satisfactory completion of Step 4 or equivalent and 15-years-old by July 5, 2015. Selection based upon application, sailing check, interview, and references. Program may be repeated, with students typically participating for 2 or 3 consecutive summers.


If you are a Boston resident who will be 15 years old by July 5, 2015 and want to apply for our Instructor-in-Training program, but have limited to no sailing experience, you should still apply.  You may still qualify to for a position in the IIT program. Please complete the application as soon as possible and email Maura Hackett, Director of Youth Programs, if you fall into this category.

For New Applicants to the IIT program

Applications are due by Friday, March 13, 2015! Based on applications, a select group will be called back for an in person interview and sailing test on Saturday, March 21. Acceptance descisions will be made no later than April 1.

To be accepted into the 2015 IIT program, you must:

  • Be 15-years-old before July 5, 2015;
  • Have successfully completed a full session of Step 4 in 2014, or its equivalent

(Important: If you have not completed this course and would still like to be considered for the Courageous IIT Program, please contact the youth program director immediately; in 2015 this may not necessarily exclude you from becoming an IIT)

  • Obtain a current First/Aid CPR certification (Note: IITs areresponsible for covering the cost of their own certification)
  • Complete the online IIT application form by clicking here (requires you to upload resume, cover letter, and application essay)
  • Wow the Program Director in an Interview (DATE CHANGE! To be held Sunday, March 15, 2015 [Last updated 02/25/15])
  • Ace a Sailing Check-Out (DATE CHANGE! To be held, Sunday, March 15, 2015, weather permitting [Last updated 02/25/15])
  • Commit to the full 7-week program, from June 29, until August 14, 2015

For 2nd Year or Returning IITs

If you have successfully completed the 1st year of the IIT program and wish to return for another year, please email Maura Hackett, Director of Youth Programs, to notify her of your interest in being considered for rehire. If you do not notify her by March 1, 2015, 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.

For IIT Parents

If you are a parent or family member of a student who would like to become an IIT or return for their second season as an IIT, please click here for more information about the 2015 program, including elligibility, the application process, program dates, student expectations, compensation, and more. As there is a lot of good information in this document, it is probably a good idea for all IIT applicants to read it, too. 

For Boston Residents Only

Apply to the Department of Youth Engagement & Employment's Summer Employment program (formerly known as the Boston Youth Fund Hopeline Program). The 2015 online application period will begin Monday, February 2, and end Friday, March 27.  For more details and to apply, click here:

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 you school, primary care physician,a parent/guardianand 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.
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