• 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

How To Help

Keel Campaign

The Courageous Keel Campaign is designed to ensure that Courageous has the financial reserves necessary to continue to serve Boston kids for many years to come. The Courageous Board of Directors is contributing over $200,000, which they hope to match with another $200,000 in commitments by the end of this year.

Give Today to the Keel Campaign

To discuss structuring a 3 year gift, a challenge gift, making a bequest, or any other questions regarding gifts for Courageous Sailing, please contact:

James Benenson
+1 920 319 KEEL
Chip Terry
+1 781 570 9406
Dave DiLorenzo
+1 917 282 7464

The Courageous Awareness Campaign 

On Thursday, May 1, Courageous Sailing announced the launch of a new campaign aimed at raising awareness of its youth programs, which teach vital skills and have played a critical role in enhancing the lives of tens of thousands of Boston children during the past two-plus decades.

The campaign includes an innovative mix of TV, print, radio and web advertising, developed pro bono by ad agency Hill Holliday and Courageous board member Joe Berkeley. With beautiful photography and video, the campaign captures the essence of the Courageous Sailing mission and its impact on Boston kids.







Against the Tide 




Youth TACK RGB web

Youth TIDE RGB web

Youth PIRACY RGB web

Adult LOVE RGB web

Adult READY RGB web




Being On

Being On

Fall In Love

Fall In Love

Help A City

Help A City

In Two

In Two



They Have

They Have

Two Weekends

Two Weekends


About Courageous Sailing

Courageous Sailing is a nonprofit, 501c3 organization. Our programs rely on the generous support of a growing community of individuals, foundations and corporations that support our mission to transform the lives of Boston's kids through sailing programs that inspire learning, personal growth and leadership. Courageous truly stands out through the character and commitment of the people and organizations who help make our programs available to everyone.


Help a city kid take a different tack in life

Donate Today

Boat Donations

Your tax-deductible boat and/or equipment contribution will help support our Youth Programs, fleet improvements and other capital needs. We are always on the lookout for Stewart Rhodes 19's to add to our core fleet, as well as medium (26'-36') cruising sailboats. For equipment or boat donations, contact our Fleet and Facilities Manager FJ Ritt.


Another way to support Courageous is by donating your time and energy! Every year we have two major volunteer days: pre-season, on a weekend in mid-late April, and post-season, on a weekend in early November. If you'd like to get added to our volunteer mailing list, contact jen@courageoussailing.org.
If you have special talents or are looking to volunteer more regularly, we can always use help on the dock catching boats evenings and weekends during the season. Contact jen@courageoussailing.org and she can put you in touch with our maintenance team or our sailing staff to coordinate your time.
Thanks for your support!

The Daniel Waldon Fund

In loving memory of Daniel Waldon

Daniel Waldon was an avid sailor and fisherman who had a lifelong love of the water, from the lakes and rivers of his native Wisconsin to the Charles River and Boston Harbor. Nothing made him light up more than being on a boat. Dan was passionate about sharing his love of the water with others—he participated in the Courageous Corporate Challenge Regatta and encouraged his colleagues to sail with him. He was especially enthusiastic about and proud of Courageous’ efforts in teaching kids how to sail. This fund is established in his memory and in the spirit of his lifelong love of sailing. Thank you for contributing to the Daniel Waldon Memorial Fund.

Please write a check payable to Courageous Sailing Center for Youth and indicate in the memo line that it should be submitted to the Daniel Waldon Memorial Fund. Checks can be mailed to: Courageous Sailing, One First Ave. Charlestown, MA 02129 or delivered by hand to the boathouse on Pier 4 in the Charlestown Navy Yard.


Life as a Courageous Kid
Youth Program
My 18th birthday, this April, inspired me to do some serious thinking about what it means to be mature and how I define adulthood. At the same time that I was working through these big questions for myself, I became a member of the senior staff for the first time at Courageous. Although I ...
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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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Find Us

Pier 4, Charlestown Navy Yard, Boston, MA 02129



Thank you to our donors

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