About Courageous Sailing
Connecting Boston with its Harbor since 1987
Named for the two-time America’s Cup winner Courageous that once
lived at Pier 4, Courageous Sailing is has spent nearly four decades serving the community by promoting access to the sport of sailing and meaningful learning opportunities.
Our Mission
Courageous Sailing exists to transform lives through sailing programs that inspire learning, personal growth, and leadership.
About Courageous
Courageous Sailing has come a long way since our inception in 1987, but our core belief has remained unchanged: When kids get together on a sailboat, sailing is just the beginning of what they learn.
Now in our 4th decade, we continue to expand our reach, bringing people of all ages, communities, abilities, and backgrounds together to experience the joys of sailing and the personal growth that comes along with it.
The Courageous Vision
Watch our Video Overview
Their Lives. Our Impact.
Each year, we evaluate our programs to see how far we’ve come — and
to provide benchmarks to beat next year. Just a few things we’re proud of this year:
Our Locations
Jamaica Pond
Jamaica Pond Boathouse brings excellent sailing instruction to Boston’s largest body of fresh water. Come check out our new fleet of kayaks and standup paddleboards.
Sail in JP
Charlestown
Our Charlestown Boathouse, headquartered on Pier 4 in the Charlestown Navy Yard, provides a gateway to Boston’s inner and outer harbor.
Sail in Charlestown
Support. Sustain. Sail.
The generosity of individuals, corporate donors, and grantmakers is, and always has been, crucial to the work happening at Courageous Sailing. Thank you.
View our supporters
Our Crew
Courageous Sailing is helmed by a dedicated team of year-round and seasonal employees who, together with our Board of Directors, uphold our mission to transform lives through sailing.
Courageous Team
Board of Directors
Leadership Council
Jobs at Courageous
Opportunities on our seafaring team are plentiful — whether joining us for a season or forever.
See open Jobs
Our Fleet
From our Rhodes 19s to our cruising boats, the Courageous fleet includes a variety of boats so sailors of any skill level can find the right challenge.
See the boats
