• 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


Saturday, February 13th, 2016: Racing is Cancelled.
We will be at the New England Boat Show all week. Come by and say hello.
Boat Show Discounts will be available starting Saturday, Feb. 13th.
  • Work for Courageous

    Love sailing? Love teaching? Courageous is currently hiring for a variety of seasonal and summer jobs for our youth and adult programs. Spend your summer sailing with kids, teach sailing to adults on weekends, or help run one of our programs! Read More
  • Summer Youth Program Registration

    We’re gearing up for another awesome summer of sailing at Courageous in Charlestown and at Jamaica Pond! Our 2016 programs will run between Tuesday, July 5 and Friday, August 19. The online lottery for registration opens March 1 and closes March 15. Our need-blind summer sailing program offers sailing instruction at a variety of levels for kids aged 8 and up. Read More
  • Sail Boston Harbor!

    At Courageous, we’re committed to providing some of the best and most affordable sailing opportunities on Boston Harbor for adults and families. Whether you’re a total beginner or an expert sailor, we’ve got a course or membership to fit your needs and interests. Read More

Recent News

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Pier 4, Charlestown Navy Yard, Boston, MA 02129



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