A tradition is born.

Thanks to our partners and supporters, we have sent the awesome 5th graders from Northwest Elementary School out on the Liberty Clipper for the past four years, and in 2019 Johnny Appleseed 5th grade joined the fun!

We have now helped more than 600 young pirates set sail.

Let's make 2020 be the best year yet.


Captain Christopher Shaw was a beloved tall ship captain who we lost in 2015. We miss him everyday. His memory continues to inspire so many friends, family members, and sailors around the world.

And now this sail program is bringing some of Chris' spirit, energy, and leadership to young people in Massachusetts!

Chris sailed all over the world, but he always called Massachusetts home. He often talked about getting young people from his hometown of Leominster out on the ocean. He knew that the whip of the wind in the air could carry anyone's imagination, and could do wonders for those struggling at home or at school.

Our Mission

Our mission is to support young people in Massachusetts to experience and learn about the ocean, sailing and tall ships in New England and around the world.

We fund and organize school field trips to sail on tall ships in the Boston Harbor. We started the program in Leominster, Mass because that is where Chris Shaw was raised. We get youngsters from diverse and underserved public school districts out onto the open water and onto, in most cases, their first ship at sea. 

We aim to foster a sense of exploration and new horizons for kids that might not otherwise have the opportunity - To give them a sense, that anything, truly, is possible.

“Twenty years from now you will be more disappointed by the things that you didn’t do than by the ones you did do. So throw off the bowlines. Sail away from the safe harbour. Catch the trade winds in your sails. Explore! Dream! Discover!”
— Sarah Frances Brown, from "P.S. I Love You"