• 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


Special thanks to our Courageous Sailing foundation, corporate, and philanthropic partners.



Cummings Foundation MableLouiseRileyFoundation Anonymous

$20,000 to $100,000

John Hancock logo Distrigas-Logo peterson party center LG

$10,000 to $20,000

Harvard Pilgrim Fallon Company 11th-Hour-Racing-Logo No-Tag-Line-300x124 TK Logo cmyk hi-res-1024x347

$5,000 to $10,000

Fortress Coyne-Fund-Trust Mesirow Mellon Capital
Barefoot-Regatta-Logo alphagraphics logo Fidelity State-Street-Logo Bain Capital

$1,000 to $5,000

Marcum LLP

Commvault Systems

Joanne L. Shrontz Family Foundation


WJ Lynch Associates

State Street Foundation

HBB Foundation

Boston Boatworks

Premier Bartending & Beverage Service



Bank of America Merrill Lynch



Sperry Top-Sider

Leggat McCall

Mayflower Advisors

Boston Private


Patriot Energy

Atlas Venture

Eaton Vance

Brooklyn Boulders


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. Support comes in many forms, from an annual volunteer day to a donated auction item, from giving $5 at a weeknight cookout to heading up a team in our annual Corporate Challenge. Courageous truly stands out through the character and commitment of the people and organizations who help make our programs available to everyone.

Individual Support

Personal donations are a key part of our funding. Every gift helps, and every time you come to Courageous you are doing your part to support our programs. Whether you are a new or long-time member or you just came down with a friend to try racing one evening, you are helping to support Courageous kids and increase the community's access to Boston Harbor. We thank everyone who has given to support our mission. To give, click here.

Community Partners

Strengthening and extending the relationhips in our community is a foundational principal of Courageous Sailing. We establish community partnerships as a benefit to our members as well as those outside of our organization. If you are interested in becoming a community partner, please contact Dave DiLorenzo at dave@courageoussailing.org Current active members of these organizations are invited to enjoy 10% off individual and family memberships and 10% off most learn to sail courses.


BKBS CBI Piers Park


Neighborhood Partners

We are fortunate to have location in the Charlestown Navy Yard with a number of residential and commercial neighbors in the surrounding blocks. As a member of this community with a historical connection to Boston Harbor, Courageous is proud to offer easy access to sailing for our neighbors. For information about special neighborhood pricing and events or to learn how you can become a neighborhood partner, please contact Dave DiLorenzo at dave@courageoussailing.org


spaulding MGH YMCA
Unknown  CWC charlestown seal

The Waiver

The Courageous Sailing Agreement & General Release and Membership Terms & Conditions form, also known as the 'Waiver' is required to participate in all activites hosted by Courageous Sailing at our Charlestown Site. All participants, members, guests, etc. must sign the waiver once per season. The form is available below for electronic download. We encourage you to review it carefully so you understand your rights and responsibilities. The form is electronic, so you may complete it on your computer, phone or tablet. You may also print it out and bring it with you on your first visit of the season. Hard copies are available at the front desk should you wish to fill it out when you arrive.

For Over 25 Years, Courageous Sailing's mission has been to transform children's lives through sailing programs that inspire learning, personal growth and leadership.

More Articles...

  1. Charlestown


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...
Continue Reading...
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...
Continue Reading...
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...
Continue Reading...
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...
Continue Reading...
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...
Continue Reading...

Find Us

Pier 4, Charlestown Navy Yard, Boston, MA 02129



Thank you to our donors

Distrigas Logo BNY Mellon State Street Logo
alphagraphics Triumph Modular Building americorps Parks and Rec premier capers catering peterson party center gordons wine and liquor Catering Name Tag