The Courageous Youth Programs

In just one lesson you'll be out on the water. If you like it—which we're sure you will—before long you'll be skippering a boat, racing on a team, or cruising around the harbor islands. If you stick with it, one day you could even be a Courageous instructor!

While you're on the water, you're going to learn lots about the environment, and get to practice some pretty important life skills, too. From fishing off our pier to overnight island camp-outs, we'll keep you having fun on adventure after adventure, all year long!

The Summer Youth Program

Our Youth Program is based on a Five Step approach. Start off in Step One to get a taste of the excitement—it's only the beginning! From there, you'll work through the steps from summer to summer, having more fun and learning more than you ever thought possible on your school vacations. And in a just few years, you might very well find yourself in Step Five as an instructor!

And we're about more than just sailing. In our classes, from your instructors you'll learn a lot about the marine environment, as well as about what it takes to be a leader both on and off the water.

The best part is that your instructors are having just as much fun as you are!  Our passion is the water, and we hope it will become yours, too!

Class Descriptions • IIT Program • Summer Calendar • FAQs • Lottery Information

School & After-School Programs

Expanding youth sailing in New England beyond its traditional summertime boundaries, Courageous has a growing range of spring and fall offerings. We have spring and fall programs specifically tailored to the needs of local public schools, advanced after-school programs for our summer sailors who want a little extra practice, and programs for groups of first-time sailors who want a taste of what it feels like out on the water.

After-School Sailing
This program in Jamaica Plain is open to students who have sailed with us during the summer in Step 3 or above. This is an open time for students to practice the new skills learned over the course of the summer. Some sessions may have a specific focus, such as racing or cruising. After-School sailing is at Jamaica Plain locations.

School Programs
Courageous Sailing partners with public schools throughout the city to offer specially tailored programs that will enhance your students' experiences. These programs are offered primarily at Jamaica Plain and schools must be Boston Public Schools. Past school partners include Warren-Prescott Elementary, The Young Achievers Pilot School for Math and Science, Codman Academy, and the JP Manning School. To find out if your school can participate, email or call  This e-mail address is being protected from spambots. You need JavaScript enabled to view it at (617) 242-3821 ext. 12.

High School Racing Teams

Several competitive high school sailing teams train at Courageous' sites in Charlestown or Jamaica Pond. Whether a school is putting together a team for the very first time or has an already established team that needs a new place to sail, Courageous has been able to come through for local schools.

Current high schools that sail at Courageous include BB&N, Boston Latin, and Boston Public Schools (district-wide team). To find out if your high school can participate, email or call This e-mail address is being protected from spambots. You need JavaScript enabled to view it at (617) 242-3821 ext. 12