Participants in Courageous Sailing’s summer programs learn teamwork and cooperation through sailing. Students participate year after year and can eventually become Instructors-in-Training.

Key Takeaways

  • Good peer relationships take time to cultivate, but can be facilitated through group activities.

  • Cooperation and teamwork can be learned as necessary strategies for reaching a goal (such as sailing a boat).

  • Positive peer interactions are evidenced by genuine concern for and desire to be with one another.

  • Daily reflection can be used as a strategy to troubleshoot conflict or other difficulties.

Q: Describe a typical relationship between peers at your program (e.g. are they best friends?). What does your staff do to promote these types of relationships?

A: For our Swim Sail Science program, the kids come from four different schools and two different grades. We intentionally separate the children into four different groups that are a mix of grade level and schools. The first day is spent playing name games and doing team building activities. We incorporate team building into our daily schedule to continue to build relationships throughout the summer. The kids do not typically know each other well at the start but by the end of the five weeks, most have cultivated friendships with their peers, and often when they come the following year, they are excited to see their “best friends.”


Our Steps To Lead program is a little different. Students hail from all corners of the Greater Boston area and our younger students do not usually know anyone in their Step. Our program is super sticky and often kids start with us at age 8 and go all the way through age 15. By the time they’re 10 or 11, they’ve been coming to Courageous for several years and have built strong friendships with the peers moving through the Steps with them. Again, we make sure we do a lot of very intentional team building at the very beginning, and sailing is a natural team building activity.


Then there’s our Instructors-in-Training (IIT) program for 15 and 16 year olds. The majority of IITs have been with us since they were 8 years old. Most enter into the IIT program as best friends, and we have some that will refuse to leave each other’s side; the camaraderie in that particular group is very high as they have spent many summers together sailing. Even so, IITs that are new to Courageous are welcomed quickly into the fold.

Q: Do you mind giving an example of one of the team building activities?

A: We incorporate names games into the beginning of the program and usually do some kind of scavenger hunt at the beginning. Some staff team building favorites include “chocolate river,” and “human knot”.

Q: What are some examples of positive interactions you’ve seen between youth at your program?

A: My favorite: we had a student that had developed a close friendship with one of the other students. While sailing, we have three in a boat and an instructor. It was a windy day and one of the girls had her favorite hat on and the wind blew her hat off, into the water. If you’re familiar with sailing, you know that it’s not particularly easy to maneuver a boat back to where her hat came off. The student was notably upset but the rest of the group did a great job of working together to tack back around to where her hat had fallen off. They were genuinely concerned for her and wanted, almost as much as she did, to find the hat. It was really cool to watch the kids work as a team and be so invested in someone’s well being.  At first, they weren’t able to find it and concluded that it had sunk but refused to leave it at that and insisted on all pitching in to buy her a new hat. Luckily, when they arrived back to the dock, they found it on the rudder. That’s one of my favorite stories, that’s what it all about.


Overall, in our Instructors-in-Training (IIT) program, they insist on doing everything together. Some have graduated to staff this year, and emailed us saying, “I really enjoyed spending time with one of our other Instructors-in-Training, I would love to be able to work with them as staff, I think we would do so well together.” Emails like that aren’t uncommon and are more evidence that are students are building strong peer-relationships.

Q: What do you do to ensure that youth respect and listen to each other?

A: We put a big emphasis into our training on listening to students’ concerns. We train our staff to make sure that when something happens, that they’re addressing both their own and their student’s concerns; it serves as a good way to model for our students. We also build in time for reflection into our program, to make sure that we’re addressing challenges, and that usually helps us troubleshoot conflict before it escalates, and helps our staff better facilitate respectful conversations. We rely a lot on our staff both to model and to facilitate those respectful interactions.

Q: What do you do for the reflection activities?

A: It’s short and simple, all we’re asking is, “What’s challenging today? What could we have done better? What do you think went really well?” And our students do a really good job of articulating that, and then our instructors try to troubleshoot based on what they say.

Q: What do you do to ensure that youth cooperate with each other?

A: Sailing naturally lends itself to learning cooperation, and that’s our core activity. In sailing, you can’t get anywhere without the help of someone else; we use it as a platform to teach teamwork and communications skills. Our instructors are also given a wide variety of drills and practice suggestions to do each day that are geared towards promoting work as a team. They’ll do scavenger hunts on the water, they’ll do races which, again, promote teamwork between two people, or they’ll do drills that promote teamwork. We play tack a tag a lot, which is basically tag on the water: there’s two people on a boat that have to get somewhere so they can throw a tennis ball at another boat.


At Courageous Sailing, youth experience sailing as a platform to develop leadership skills, gain confidence, explore Boston Harbor, and delve into hands-on science. The Swim Sail Science program is a 5-week summer program for Boston children that blends academic support with sailing lessons, swimming instruction, and hands-on marine and physical science. The Steps to Lead program involves youth experience sailing as a platform to develop leadership skills, gain confidence, explore Boston Harbor, and delve into hands-on science. The Instructors-in-Training program is a 7-week summer job-training program where students make the transition from student to instructor, developing their abilities to teach, lead, and inspire the next generation of Courageous kids.