Sea Challenge

“The Captain called it Sail Training…We called it fun!”

– Tom S., Student Sea Challenge 2016

Sail Portsmouth’s Sea Challenge program provides high school students from the Seacoast region an opportunity to participate in an adventure-filled, experiential education program aboard tall ships.

Sail Training

Sail Portsmouth believes many people learn best when working with their hands, their hearts, their and their souls. rather than when sitting in a classroom or in front of a computer screen. Living and working as one of the crew on a tall ship is an ideal setting for all kinds of learning and transformation.


Tall ship sail training is both experiential and educational. Participants work alongside the ship’s crew to sail the ship toward its destination in a safe and efficient manner. They climb masts, adjust rigging, navigate, steer, cook, stand lookout and much more. Each trainee is as dependent on the team as the team is dependent on them.


Students often come back with a sense of transformation, having traded the comfort and familiarity of their homes and digital devices for the rigors, sights, and sounds of the sea. Often, on the last day, they are reluctant to leave the ship and their shipmates. They know they will miss the fun times and meaningful conversations. They return to shore with new friends, vivid memories, and pride in their accomplishments.


“This was the best experience of my life.”     

Declan M., Student Sea Challenge 2019

 Tall Ships

The ships can be two-masted schooners and three-masted square-rigged ships. All are regularly inspected and certified by the U.S. Coast Guard. The safety of the ship, crew and passengers are the Captain’s number one priority.

Recent Sea Challenge ships in the program have included the schooners Roseway from Boston and Harvey Gamage from Portland, and the square rigger Oliver Hazard Perry from Newport.


Sail Portsmouth recruits students from diverse backgrounds with the help of traditional and alternative high schools as well as several community youth organizations. These organizations identify youths who they believe will benefit from this kind of challenging and inspirational trip.


The cost is $1,500 for a week at sea. We realize many families cannot afford the full tuition. Our philosophy is that no one who wants to go gets left behind. That’s why we created the Sea Challenge Scholarship Fund. If Sea Challenge interests you, please contact your school counselor or, complete the short Sea Challenge request for more information on this website, hit the LEARN MORE button. Someone from the Sail Portsmouth will be in contact.

 “Sail Training is not about learning to sail. It is about learning from sailing. From the ship’s crew…From the sea…From oneself.”

– Kris von Wald, Executive Director, Tall Ships America

Sea Challenge 2018

Roseway 2019 BDEA Trip

Apply for the 2021 Sea Challenge Voyage


It’s time to sign up for the 2021 Sea Challenge program. For detailed information and answers to all your questions, whether you are interested for yourself, your child or your student, please select the Contact Me button below, complete and submit your contact information. Someone from the Sail Portsmouth will contact you.

Send a Deserving Teen to Sea

For $1500 you can send a deserving teenager from an underserved family to sail training for one week. Sea Challenge voyages scheduled for this Summer 2021.