How To Help

The 30 Day Challenge

Get Your Gift Doubled!

With summer sailing right around the corner, there's a lot to do before the kids arrive at the docks, but you can help...

Join our “30 Day Challenge.” We’re looking to raise $10,000 in 30 days (Between April 5th and May 5th at midnight) to do more for Courageous kids. To sweeten the deal, there is also a matching challenge (until the fund runs out), so that means whatever you give will have double the impact!

Here’s how it works: If you give $500 then another $500 will be released from our Matching Fund. If you give $1,000 then another $1,000 will be released to Courageous essentially doubling the impact of your gift. Double your impact right now by giving a gift in ANY AMOUNT and help Courageous get ready for some smooth sailing this summer.


Give to Courageous

  Provides two life jackets for two children

  Provides a week of programming for one child

  Provides two weeks of programming for one child

  Supports one child through the entire Swim Sail Science! program

  Give any amount to support Courageous kids 

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.

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

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
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 and she can put you in touch with our maintenance team or our sailing staff to coordinate your time.
Thanks for your support!