• Explore. Learn. Sail! Low-cost, high-quality programs that connect city youth with Boston Harbor and Jamaica Pond. Youth Sailing
  • Sailing and rowing for kids, adults, and families on this beautiful pond located in the heart of Boston. Jamaica Pond
  • Work at Courageous

    The 2015 season is just around the corner, which means there is an opportunity for you to come spend your summer working at Courageous. You'll be outside and on the water with a great staff and sailors from age 8 and up. This could be the start of your lifelong passion for teaching sailing, educating, and organizing in your community. 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
  • Environmentalism at Courageous

    Courageous is wind powered, but we do more than just use natural energy sources. For the past several years, our young sailors have been learning about marine biology and ocean cleanup from our own Environmental Educators and award-winning partners. Read More
  • Support Courageous Kids

    As 2014 draws to a close, Courageous is celebrating a successful year of teaching sailing and more to Boston kids, and looking ahead to next year. Please consider supporting Courageous in our mission to provide high-quality summer learning opportunities for the kids who need them most by making a tax-deductible donation to our Annual Appeal before December 31. Read More
  • Awareness Campaign

    See our new awareness campaign made by Hill Holliday and Courageous board member, Joe Berkeley. The campaign captures the essence of the Courageous Sailing mission and its impact on Boston kids. Read More
Pictures & Videos
Speaking my Language
Youth Program
This summer, I was a sailing instructor in Courageous' Swim Sail Science program (otherwise known as SSS). The SSS students are from various diverse backgrounds and live all over the city of Boston. With that being said, the kids represent several different ethnicities and do not always speak Englis...
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Experiencing the J/80s
Youth Program
This past spring, Courageous received a donation that allowed the purchase of two J/80s.  J/80s are 26-foot-long sloop-rigged sport boats, with a roller furling headsail and an asymmetrical spinnaker.  The intention is, assuming Courageous likes the J/80s and finds that they suit its needs...
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A Place for Growth
Youth Program
This summer, my second at Courageous, I had the opportunity to gain a greater understanding of the Youth Program as a whole. Previously while working with the Instructors in Training, I only had a narrow view of that one piece of Courageous. Returning to Courageous, I was excited to become a part of...
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How Blue Note came to Courageous
One of of my favorite stories of 2015 is the arrival of Blue Note.   A comfortable yet sprightly 30 footer in wonderful condition, Blue Note comes to us through the generosity of the family of Dr. Paul Blum, a remarkable scientist, Peace Corps volunteer, and Boston Harbor sailor.  Blue Not...
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Fear and 420s
Youth Program
For most Courageous students, their first day of step 4 is their first time in a dinghy, a transition from a stabile Rhodes 19 to a more responsive 420. This transition isn’t easy. The rounded lines of 420 belie how uncomfortable it is to sail—you’re guaranteed to sit on a cleat and bump your shin o...
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