Sailing, marine life, and field trips are part of a program to prevent a summertime loss of reading and math skills among low-income students in Boston. Its aim is to help close the achievement gap. On a sweltering August day, student Hendrick Estrella sits on a sailboat, dragging his hand through the waves and reveling in the coolness of Boston Harbor. The day before, he had touched – and tasted – a striped bass, gathering details for a book he is writing about fish. 

Courageous Sailing was recognized by SAIL Magazine as one of the top ten community sailing centers in the country. What set Courageous apart was the organization's involvement in Special Olympics and Sail Blind among other adaptive sailing programs. SAIL mentioned how Courageous has played an important role in making the waterfront accessible in the summer for non-caucasian youths from lower income backgrounds.

US Sailing, the national governing body of the sport of sailing and standard bearer for sail training in the United States, has recognized Courageous Sailing as one of the best community sailing centers in the country. Courageous offers sail training from the very basics all the way through advanced keelboat courses, bareboat cruising, and celestial navigation. In addition to Courageous, US Sailing recognized only eight other sailing centers.