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.

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:
BIPOC students made up more than
of participants in our 2023 summer programming
2 out of 3
summer sailors received scholarship support and 57% participated for free
of summer students feel more likely to persevere through challenges because of Courageous

    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


    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