Courageous Sailing is a Boston nonprofit whose youth sailing programs are completely free, serving over 1,000 kids a year from its Charlestown Boathouse on Pier 4 in the Charlestown Navy Yard and at Jamaica Pond. More than 400 area youth spend a summer learning to sail across the two sites each year. Its five-week Swim Sail Science program, run with Boston Public Schools, pairs sailing and swimming with a hands-on environmental-science academic curriculum for sixty elementary students a summer who are at risk of learning loss, and includes school bus transportation and meals. Summer places are allocated by lottery with a registration window from February 1–15; Swim Sail Science is limited to students identified from a set of partner elementary schools.
The practical details
We list only what the camp itself publishes, and programs change — dates, prices, ages and availability can all move after we check. Confirm the details on the camp’s own website and contact Courageous Sailing directly before you register or pay. Last checked August 2026.
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★★★★★Pete FreemanA great way to enjoy the harbor. The staff is friendly.
★Nicole BerlinMy husband and I were excited to do Learn to Sail parts 1 and 2. We will never be returning after a horrible, demeaning experience. The weekend of our first lesson was predicted to be in the 50s and raining in June. We asked Caitlyn to change weekends due to concerns about the dangerous conditions and were told no because they would then have empty spots. We explained why we needed to switch for health reasons, we were ignored. We went to the rainy, cold lesson so that we did not lose $800.00 and I ended up with borderline hypothermia. Then our second weekend of lessons there was no wind and instead of cancelling we sat in boat while two different instructors, one who was in high school and incompetent, told us random I formation and explained they couldn’t teach with no wind. My husband then called and spoke with Caitlyn and the executive director after one of the experienced instructors was horrified by our experience and agreed we should be refunded. Caitlyn proceeded to give my husband a difficult time (after ignoring my health issues when we called the first time) and would only issue a partial refund. We were treated poorly, received inconsistent and downright bad instruction, and Caitlyn outright lied to the executive director that we had asked to switch weekends for health concerns. We will never return and caution anyone who spends $800 PER PERSON on lessons just to be treated like garbage. We are moving over to Community Boating and never looking back. Avoid avoid avoid!
★★★★★Jules Oscar Gaudreau IIIRecently completed a "Learn to Sail - Complete" class at Courageous in preparation for the US Sailing "Basic Keelboat" certification. I am impressed by the quality of instruction they provide, and the ease of working with their office team. Classes were fun and informative with a strong emphasis on practical skill development; we spent a lot of time on the water and all three of the instructors who worked with my group were excellent. All-around great organization. Friendly, competent staff and instructors. Nice-sized fleet of boats. Awesome location in Charlestown. I've been sailing for eight years, but this was my first class, and I can happily recommend Courageous Sailing for anyone with an interest in learning how to sail or honing their skill set.
★★★★★Carolyn CervaMembership is worth it- nice people, great instruction, and lots of opportunities for group lessons/extra help.
★★★★★Michael O'Brien (Michael George O'Brien)Courageous is my favorite mission driven sailing school. I have learned so much there and met so many awesome people, and I love that youth sailing programs are funded by adult sailing lessons, events, and local sponsors. It is truly a staple of the community.