• Convenient and affordable courses, lessons, and memberships for all experience levels and interests. Sailing for Adults + Families
  • 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
  • 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
  • Give the Gift of Sailing

    If you’re looking for the perfect last minute gift or treating yourself to summer of sailing next year, now is the time to take advantage of our Holiday Deals. Through December 31, lessons, courses, and memberships are up to 50% off. With sailing opportunities for all ages and experience levels, Courageous has something for everybody on your list! 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
  • Environmentalism at Courageous

    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

It’s time to go sailing!

A Courageous membership means that you can take one of our boats out for a sail on Boston Harbor whenever you’d like*.  Courageous offers a variety of memberships to fit all schedules, skill levels, and boat preferences -- check out the different options, and see which one works best for you.  Membership also includes much more: barbeques, racing, fireworks-watching parties, moonlight sails, Harbor Island camping trips, and discounts on courses.  As a Courageous member, you’ll be a part of an enthusiastic, inclusive community of sailors...and you’ll be helping Courageous provide free and low-cost sailing opportunities for Boston kids.


*Skippers must pass an on-the-water check-out and written test in order to sail a Courageous boat without an instructor.  Our sailing area extends out around the Harbor Islands for qualified members.  Courageous is open noon - sunset on weekdays and 10 - sunset on weekends and holidays, May 1 through October 31.  Boat availability is usually plentiful, but is not guaranteed.

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Frostbiting Week 4: There is always a lot to learn.
Frostbite
Hello Frostbiters, I trust that everyone had a great weekend and Nate ran things well in my absence. Before this week's guest blog by Mark, I have two announcements to share. We have two special events this upcoming Saturday, Rules Clinic, at Seaport School, this Saturday, December 20, 9:30-11am...
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Week 3 Recap: Overtaking at the Windward Mark
Frostbite
 I hope you are all staying warm and dry today. It is one of those days that you don't have to walk far before you look like you've fallen off the dock or been swept overboard. The good news is that this weekend should be warm (high of 45) and dry, with NW winds around 10 knots. I am taking a...
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Frostbing Week Two- Starts Are Hard
Frostbite
Barge- Move forcefully or roughly. Push, Shove, Force. "We can't just barge into a private garden party." or "Barging in at the start line causes havoc and makes Courageous staff anxious and competitors angry." Yes, this week's recap is about starts, and in particular, barging. Which there was a ...
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Week 1 Brings Great Weather, Great Racing
Frostbite
Current was coming straight down the course all day, making starts difficult at first. As the current slacked, the fleet was still pushing hard and we had several boats OCS, but no general recals occured.  In Race 1, the boats starting pin got over into a nice lefty shift, and were able to t...
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Welcome to the 2014-2015 Frostbiting Fleet!
Frostbite
Our first day is in just two weeks (November 15), so what should you be expecting? The best racing in Boston, with 25 boats on the line Newly re-painted and buffed R19s Evenly tuned boats (so no adjusted rigging!) Experienced support boat and RC staff A great group of highly skilled and c...
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