• Explore. Learn. Sail! Low-cost, high-quality programs that connect city youth with Boston Harbor and Jamaica Pond. Youth Sailing
  • Convenient and affordable courses, lessons, and memberships for all experience levels and interests. Sailing for Adults + Families
  • Sailing and rowing for kids, adults, and families on this beautiful pond located in the heart of Boston. Jamaica Pond
  • Corporate Memberships + Outings

    Purchase a 10/20/30 pass for your company and give your employees access to Boston Harbor all summer long. Each pass includes a 3 hour sail in one of our boats for 4 people, plus an experienced, knowledgeable instructor to be their guide. Read More
  • Environmentally Friendly

    Courageous is wind powered, but we do more than just use natual energy sources. For the past several years, our youngsters have been learning about marine biology and ocean cleanup through award winning partner programs. Read More
  • Leadership + Growth

    Through this 7-week summer job-training program, students make the transition from student to instructor, developing their abilities to teach, lead, and inspire the next generation of Courageous kids. Read More

Recent News

College Sailing: The First Month In


Sailing is not a pleasure that is typically afforded to kids that live in the city. I was fortunate enough to have been introduced to it through Courageous Sailing in more ways than one. First, my initial contact with sailing when I was 8 years old in their youth program, then yet again once I became a freshman at Boston Latin School, finding out that maybe I wanted to try doing it at a competitive level. There were rough patches (including my almost being asked to leave the team) initially, but by my junior year I knew that it was something I wanted to pursue seriously; so I did.

To go from “almost-kicked-off” to co-captain in a few short years is something I believe took a development of leadership skills only possible on teams like the sailing team at BLS. In order to get serious about becoming better, I had to become serious about conveying a positive message and being a leader to the others on the team, younger and older.

The schedule was not always easy, but it was always fun. I began to pay more attention to other sailors and the coaches and focused on maximizing my time on the water. I also began to take advantage of the fact that we practiced at Courageous, which offers various racing programs throughout the year (even winter!). That being the case, I looked into an opportunity to race a Rhodes 19 in the frostbiting series with some very competitive, knowledgeable people in the harbor. Although there was an entry fee, Dave allowed me to race on days where there were openings, and I believe I learned more that season about boatspeed on my own than ever before. Looking at the people at the head of the fleet, it became clear to me that making a sailboat go fast would be a challenge that I could undertake for the rest of my life. I was fortunate enough to earn MVP both my junior and senior year of high school under my coach Dave, a great honor and testament to the fact that my hard work was paying off.

Then came college. College racing is (even now) a very new and scary world to me. Everybody is faster, the community is bigger, and I am learning the necessity of being a team player more than ever. While I was frostbiting and holding as many conversations with the people around Courageous as possible, I realized that sailing is all about networking. People like Dave, Carl Zimba, and all the numerous college and ex-college sailors that I met really gave me an idea of what I could expect if I tried out for the team. As I write this now, I am a little over a month into my freshman year at Boston College, and a few weeks into being a part of the BC varsity sailing team; one of the best in the country. While I am certainly not MVP-status at this elite level, sailing on the BLS team in high school taught me what qualities and efforts are expected from a freshman who is aspiring to reach that level.


Jack Flaherty

Boston College '17




in Racing Hits: 24922

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