To transform lives through sailing programs that inspire learning, personal growth and leadership.


Courageous will be a national model for innovation and best practices in youth development. We will increase opportunity and reduce achievement gaps for youth from marginalized and low-income households. We will grow a diverse and inclusive community of youth from all backgrounds. We will nurture and inspire our students’ academic achievement and social-emotional growth. We will build this on a foundation of sailing excellence, in which the acquisition of hard skills is tied necessarily and intentionally to broader outcomes. We will remain deeply rooted in a community of sailors, educators and supporters who embrace our mission, and whom we engage through year-round programs, memberships and courses. We will develop the leadership, infrastructure and financial capabilities to sustain this model long into the future.


Courageous Sailing was established in 1987 as a 501(c)(3) by the late South Boston sailing enthusiast Harry McDonough. It was Harry’s dream to use sailing to build character and camaraderie among Boston children from all economic and ethnic backgrounds. For 25 years, we have continued to grow and deliver our mission to transform children’s lives through sailing programs that inspire learning, personal growth and leadership. In Harry’s words, “Every child’s perspective is improved 50-yards off-shore.”

Courageous is now a nationally recognized year-round educational center for community sailing and youth development. Courageous offers Boston-area youth free and low-cost out-of-school-time programs in sailing, environmental education, job skills development, and leadership training. In 2011 we were honored to be named one of the top 10 community sailing programs nationwide by both US Sailing and Sail Magazine.

How Courageous Got Its Name

The America’s Cup 12 meter “Courageous” once lived at Pier 4 in the Navy Yard. This two-time America’s Cup winner lent its name to Courageous Sailing in the late 1980s. The boat now resides at the Museum of Yachting in Newport, Rhode Island, where it has been restored and is still being raced.