Recognized as one of the top community sailing programs in the country, Courageous Sailing offers year-round sailing and learning on Boston Harbor and Jamaica Pond.

LEARN ABOUT OUR IMPACT

See what makes learning to sail so transformative.

WATCH VIDEO NOW

The Flip Flop Regatta returns on August 9. Join us as a sailor or for the post race party on the pier!

Sign your company up for the Courageous Corporate Challenge!

Set yourself up for a season of sailing Boston Harbor

Wind Powered.
Mission Driven.

Be a part of our mission to transform lives through sailing. Join us on the water for a day or the whole summer, or support us at one of our signature events.

Youth Programming

A day on the water is more than just fun. In our youth programs, sailing is a platform to help a diverse community of kids gain leadership skills, confidence, and hands-on science experience.

Explore Programs

Adult & Community Sailing

Whether it’s your first time on a boat or you have miles of water under your keel, we offer a variety of classes, memberships, and opportunities to get underway.

Sail with Us

Host an Event

Take to the sea for a private excursion aboard our fleet, or opt for our stunning outdoor space on Pier 4. Either way, you'll enjoy some of Boston's most stunning views.

Start Planning

Give & Support

We are committed helping kids from many walks of life experience all that Courageous, and the sport of sailing, have to offer — and we can only do it with your help.

Get Involved

There is an incredible culture of joy and excitement…Youth are given a great deal of responsibility and are having a lot of fun while developing crucial skills like communication, teamwork, and problem solving.
—National Institute of Out-of-School Time-trained program observer

Sailing with Courageous makes me feel proud, confident, cared for, like my opinions matter, a leader.
—Step 4 Student

Courageous made a difference in [my son’s] life...He can solve problems ‘on his feet’ a lot better and feels much more confident in stressful situations. COVID had really done a number on him. He was feeling afraid a lot. That really changed after the three weeks he spent with you.
—Courageous Parent