• 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 2015 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
  • 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
  • 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

New Rhodes 19 Sail Fund

Here at Courageous, we are already looking ahead to next year, and we want to provide our members and youth sailors with new Rhodes 19 sails! That is why we dubbed our fall Cocktails event as "Cocktails for Mainsails!" All proceeds are going towards new Rhodes 19 mainsails and jibs - which in turn will help us to provide key programming for kids and adults alike in the upcoming year. Cocktails for Mainsails started us out in the right direction, but we still need to raise more funds to reach our goal of $29,000.

We want to provide the best service possible to our members, and we also strive to teach Courageous kids the tools they need to succeed in life. Equipment upgrades are vital to our ability to deliver high-quality programming and to teach life skills through sailing. Each year, one donation at a time, our supporters make Courageous programs possible. Thank you for believing in the Courageous mission and for continuing to invest in Boston's children through Courageous. On behalf of Courageous Sailing and the youth of Boston, we extend our most sincere gratitude.

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


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 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.


Why We Keep Coming Back
Youth Program
During the summer of 2012, JB enrolled in the SLP program for the first time.  It also happened to be my first year of instructing, and it was safe to say that she was one of my most unique students.  If her constant curiosity for sailing or insistence on touching the water didn’t make her...
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Riding the Waves
Youth Program
One of the first days of Swim Sail Science! (SSS), I had a kid named Simon in my boat. He was wicked quiet and didn't seem too excited about sailing. That particular day, we were going out to the airport. The wind was pretty heavy and soon Simon wasn't feeling it anymore and became sea sic...
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More than a Sailing School
Youth Program
At Courageous, not every child wants to learn how to sail, but every child is given an opportunity to grow. One particular 9 year old, Maddox, is not as interested in learning how to sail. But he loves to be on boats, particularly standing on the bow of a Rhodes 19 and feeling the sea spra...
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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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Happy, Excited, and Free
Youth Program
For the past four years, I have had the privilege of working with students from Swim Sail Science, a program Courageous created in partnership with Boston Public Schools. The SSS program aims to serve students who are at risk of summer learning loss. These students continue their academic studies th...
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Find Us

Pier 4, Charlestown Navy Yard, Boston, MA 02129



Thank you to our donors

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