Courageous Sailing is a summer program that uses sailing to teach leadership, teamwork, partnership, and other life skills to students throughout Boston.

Key Takeaways

  • Students, while highly chaperoned, still have perceived high levels of responsibility.

  • Students are given responsibilities that they can manage, which gradually increases to help students develop their leadership abilities.

  • Through the use of check-ins and staff and student surveys, instructors incorporate feedback into program development.

  • The program excels at creating a strong sense of community and team building among the students.

  • Finding and retaining instructors with a passion for youth development and sailing skills is the program’s greatest struggle.

  • At any age, it is important to give students opportunities to feel responsible, as well as to help them reflect upon their experiences.

Q: What are two or three examples of students taking leadership roles in your program?


A: Students that are in an instructor-in-training role are responsible for developing lesson plans and teaching information to others. They might be assisting a more senior instructor in a boat and are directly responsible for the safety and learning of other students. They are supervised closely by more senior instructors.


While the perceived level of responsibility is quite high, in truth the actual level of risk that they are taking on is not as great. Making sure students feel like they have true ownership over something big is an integral part of our best practices. The emphasis is on responsibility right away.

Q: If you have a student who is struggling with leadership, are there any best practices you have to help them get there?

A: It depends on the student. Our instructors do a really good job of working with them one-on-one and give them responsibilities that they can manage. We give them little responsibilities, so they can gradually build up to the big ones. For issues with the maturity of a student, we also go back to giving as much one-on-one time as possible.

Q: How does the program incorporate student feedback into planning?


A: We have pretty extensive staff surveys. Our instructors-in-training straddle the line between students and staff, so they get all the student surveys in addition to all the staff surveys. We also use the Massachusetts Work-Based Learning Plan, so we are checking in with them three times during the summer. There is a lot of opportunity to get feedback from the team. We really try to listen to what works.

Q: What are the strengths of student leadership opportunities, as well as the challenges?


A: I think one of the strengths is how much of a team we are able to develop with these teens. We have teens from every community you can imagine in Boston. We do a really strong job of bringing these teens together and making them feel like a team.


One challenge in particular is finding people who are competent trainers, with the correct professional experience, and true appreciation for youth development. In addition, trainers have the ability to work during the summer, and continue to work summer after summer after summer. Hiring can be a challenge because we don’t have the ability to employ people like that year round.

Q: How would you apply this practice to different age groups?


A: Our programs start at the age of 8, so we are constantly trying to figure out how to give kids responsibility at all ages. It is important, if possible, to provide students with experiences in which they feel like they are being genuinely depended upon by others.


I also think it is important to both frame and debrief this experience with the student so that they have the opportunity to reflect upon and process the experience and their role in it. Without time for reflection, they may miss the point of the exercise and not recognize just how much responsibility had been given. They might not even think to use the word “responsibility” to describe their experience without being given the proper framework by an instructor.


Courageous Sailing was founded in 1987 to bring together kids from diverse backgrounds all across Boston. The program teaches them lessons in partnership, teamwork, leadership, and life skills through the support of sailing. Courageous Sailing focuses primarily on summer learning and has some after-school programs. The core of the program is to take kids, who maybe don’t have a relationship with the water, and give them an opportunity to have a new passion and have some experiences that their families might not be able to provide them with. Through these unique experiences, Courageous Sailing ignites a passion for learning and the marine environment, and teach them that they can overcome fears and can take on responsibilities. When students turn fifteen they are given an opportunity to join the instructor-in-training program, which is a job skills training program first and foremost. Courageous Sailing’s mission statement is: Courageous Sailing transforms lives through sailing programs that inspire learning, personal growth and leadership.