Dear Courageous Supporter,

To me and so many of us who love the Courageous mission, the benefits of our sailing-based youth development model are pretty obvious: teach a kid to sail, put a tiller in their hand, and they will thrive in ways well beyond sailing that can change their course in life.

Imagine yourself at eight, at ten, at twelve, overcoming your fear, working together with new friends from different backgrounds, and sailing a boat around all the obstacles that exist on busy Boston Harbor. Out of that simple model comes confidence in one’s abilities to navigate not just a harbor, but life in general. Out of that model, too, comes perseverance and critical thinking skills; social awareness and communication skills; and a belief that, with effort, one can grow and succeed.

One of my favorite stories of the summer illustrates this perfectly. It’s shared by Jenny P, an amazingly talented young Courageous instructor. In Jenny’s words:

Geraldo and Dennison are brothers in Courageous’s Swim Sail Science program. At the beginning of the summer, Geraldo, who is a year older than Dennison, would always come up to me…and remind me to “take care of Dennison, because he is so scared of boats and the water.” When…it was very windy, the boat would naturally heel over. I showed the students how releasing the main sail or heading up would flatten the boat. Geraldo would say, “Make sure you tell my brother Dennison that!” A week went by and [his] comments slowly ended. [At the end of the summer] Dennison handed me his survey and asked me to read it. What did Dennison want to tell us? That he is in love with sailing!Jenny P.

Dennison also shared in his survey that sailing makes him feel brave, that he’s proud of how he has improved, and that he wants to be a Courageous instructor one day. This is what it’s all about.

In 2017, we’ll be celebrating 30 years of making this kind of difference in the lives of Boston kids. Since 1987, tens of thousands of children have learned to sail and so much more at Courageous – 1,033 in 2016! And from the beginning, it’s all been made possible by people like you, people who believe in this mission. One gift at a time, one child at a time, you make it possible for Dennison and other Courageous kids to have life-changing opportunities on the water.

Our goal is to raise $30,000 by midnight on December 31st to support Courageous kids.

Please consider giving a gift in any amount that feels right to you. Thank you again for your continued support and generosity.



Dave DiLorenzo
Executive Director


“I fell in love with sailing”


of kids say that they feel more confident while sailing.


of Courageous kids think that practice is important for getting better at a skill.


of Courageous kids enjoy figuring out how things like sailing work.


of students agreed they are proud of how they have improved as sailors.

In 2016 1 in 3 students in Charlestown were offered

Free breakfast & lunch

Swim lessons

Daily transportation

Creating Education Opportunity

Our Swim Sail Science program makes summer learning
fun and engaging for underserved Boston area youth.

By combining sailing, swimming and academics, we help
kids avoid the cumulative effects of summer learning loss
while they make friends and build confidence, tenacity and
other life skills. This fourth year of the Swim Sail Science
program provided six weeks of academics and enrichment
for 64 rising fourth and fifth grade students from the
Harvard-Kent, Warren Prescott, Orchard Gardens and
Eliot elementary schools.


of Swim Sail Science students belong to ethnic minority groups.


of Swim Sail Science students came from families with annual earnings under $25,000.


of Swim Sail Science students came from families with annual earnings under $50,000.

Sources of support

To meet our $1.4 million annual budget, we rely on the generosity of our community.

Individual gifts, grants, sponsorships and events
Adult & family programs and corporate events
Courageous-managed sailing programs at Jamaica Pond and Camp Harborview

Courageous Sailing is a 501(c)(3) nonprofit organization. Our federal tax ID # is 04-2987534.
Donations are tax-deductible to the full extent of US law. All personal information from donors is kept confidential and will solely be used for the purpose of sending you Courageous information. We do not trade, share or sell any information of our donors to other organizations or corporations.

Join the Courageous Giving Circles

Giving Circles are another way for us to say thank you to Courageous donors.

Benefits start at the $500 level and include 20% – 50% discounts on sailing memberships, lessons, signature Courageous events and more. Consider joining the Courageous Giving Circles today and create a lasting impact for the youth of Boston.

Learn more about Giving Circles

Courageous Crew

Provides one week of classes for one child


Skipper's Circle

Provides one week for two children


Mariner's Mates

Sponsor one child through the entire 6 week Swim Sail Science program


Captain's Club

Provides daily swim lessons for 60 kids


Admiral's Club

Supports three sailing instructors for one summer, or three weeks of bus transport for children from all over Boston