Looking Out: Pre-Teens Set Sail In Outward Bound
Boston Harbor is many things to many people — a livelihood, a history book, an environmental challenge. But to pre-teen girls, sailing the harbor is a way to develop leadership, team-building skills and a strong sense of self. In this sixth installment of “Looking Out: A New View Of Boston Harbor,” we take the sails with 11 girls who leave their iPods at home and live on a boat.
BOSTON — “Heave!” they shout together, raising the sail. “Mainsail set, mainsail set.”
It’s been eight days at sea and these 13-year-old girls — many of whom had never been on a sailboat before — have mastered the craft of sailing.
Mary Katherine Horan is at the helm of what they’ve named The Sisterhood of the Traveling Boat.
“So starboard is going to sheet in and I’m going to put the helm to the port side so that we go in that direction,” Horan said.
The girls are on a 12-day course run by Thompson Island Outward Bound called Connecting with Courage. And the girls have to reach deep to find courage to live on a 30-foot sprit-rigged ketch pulling boat — a wooden sailboat with two sails and oars for rowing. At night they lash the oars across the boat and put mats down to sleep. There is no kitchen, shower, bunk beds or even private toilet.

Instructor Jane Schenk helps the students disembark. (Jess Bidgood for WBUR)
At the start of the course, when the girls arrive at Thompson Island in their cute shorts and suitcases with wheels, they have no idea what they’re really in for, though they know the thing they all fear the most — not being able to take a shower.
But they don’t know that every night they will be awakened to take a 45-minute helm watch on the boat’s bow to make sure they aren’t hit by an ocean liner. And they don’t know they will be scrubbing the decks when the muddy anchor is pulled from the ocean floor, or going to the bathroom in front of everyone as the “head,” or toilet, is tied openly to the mast. And they have no contact with home.
All of these challenges are part of what Outward Bound works into its curriculum to teach these 12- and 13-year-old girls compassion, teamwork and leadership. Rebecca Legro, from Lowell, says she’s fierce on the ice hockey rink but admits she’s timid in other parts of her life.
“I don’t really have much faith in myself,” Legro said. “I think I can’t do things but really, if I set my mind to it, I can.”
After saying goodbye and taking the ferry back to Boston, Rebecca’s father, Ken Legro, says he sent Rebecca on the program because she’s at that vulnerable age of 13.
“She’s also growing into a young lady and we’re hoping that having a change of pace with people who will take her out of her comfort level will maybe bring about a catalyst for more change,” he said.
He says his daughter will also get a perspective on Boston that he never had, even though he grew up in East Boston.

Students in the Thompson Island Outward Bound group take a quick break from sailing on Lovell's Island . (Jess Bidgood for WBUR)
“I’ve never been to the islands,” he said. “In fact that’s one of the things we said to her, ‘You’re going to see a part of Boston that I’ve never seen.’ ”
Throughout the course the girls sail from island to island in the harbor. Over time they are given more control and independence from their two instructors on the boat. They build friendships, have fights and work it out, and make up clapping games.
Research shows girls at the start of adolescence are torn between who they are and what society expects them to be. To connect with their individuality, the girls rotate through important jobs on the boat, such as cook and navigator — and Goddess of the Day.
“I feel like I can talk to people and they will listen to me because when I was goddess people listened to me,” Legro said, comparing the title to being ship’s captain. “If I just use my voice other people will, too, but I’ve always been afraid of that. I’ve been afraid to be wrong, but now it’s … OK if I’m wrong. ‘Cause I can only learn from my mistakes.”
Eight days into sailing, the girls say they’re exhausted. As their skin darkens under the relentless sun and their muscles harden, they start to reflect.
“Like every meal you have you feel more appreciative of it,” said Madison Williams, of Baltimore, “and every time you go to bed you feel more appreciative of it. You just think everything’s more beautiful. And I’ve come to appreciate my family a lot more ’cause I’ve missed them and everything, and I’ve noticed all the things they’ve done for me.”
For these girls — many of them far from home — Legro says the backdrop of Boston always on the horizon is reassuring.
“The city’s beautiful, that’s like, my comfort zone,” she said. “Every time I look at it or when I’m on anchor watch I feel like, safe, I guess. Especially at night with all the lights, it’s really nice.”

The boat sails through Boston Harbor. (Jess Bidgood for WBUR)
On Day 12 the girls are back on Thompson Island and the dirty sea salt hair, rowing blisters and close quarters are a memory. Their parents arrive to pick them up.
“Hi girls!” the parents shout. “Oh my God!”
The moms and dads have had no contact with their preteens in more than a week and so the reunion is poignant. Kyler McVay jumps like a monkey into the arms of her father, crying.
“Did you have fun, you missed us?”
The girls all say they are more self-aware and confident. But as they melt into their parents arms, they are just kids again.
And like any group of 13-year-old girls, they have a theme song that represents their experience. It’s a Miley Cyrus song and they’ve changed the lyrics to fit their time at sea.
There’s always going to be another ocean,
always gonna wanna make it smooth.
…
Ain’t about how fast I get there,
ain’t about what’s waiting on Thompson Island.
It’s the ride.
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hi, i also recently went on this sailing course. it changed the way i thought of life. my sister soon wants to go on the same course. im so excited to know my sister has a great passion for this. thank you outward bound, you have changed my life!:)
Great story about the girls. My 13 year old son recently completed the sailing course and I think it’s the best experience on his own he’s ever had! I can imagine what it did for the girls.
I was one of the girls who completed this course and I have to say it honestly was a life changing experience. It taught me things about myself that I never knew. There is so much I could say about this course, but if you are planning on taking the course yourself, it’s much more exciting if you don’t know what’s coming. You learn alot of neat things that not only come in handy on the boat, but in your everday life, plus you make friends for life. Overall, this was an inspirational experience and I would recommend it to anyone. :)
p.s. at night, we lay the oars across the boat and put our sleeping pads down. Then we roll out our sleeping bags and there we have it, our bed on a boat!
Such a cool story! My 9 yr old wants to know where she will sleep when she is on board!
I have read this article many times. And will admit,unashamedly, that I am the grandparent of one of girls who successfully completed this unique Outward Bound
Program.
This is just a note of thanks to the two instructures who carried out their responsibilities in caring for…and teaching…these 13 year old girls.
Stephen Williams,Grandparent
Fantastic….well done Outward Bound ! You are developing young folk who can face integrity, resiliance and skills that are essential and last a life time. I am encouraged and delighted. jsd Outward Bound Hong Kong
Hello all, I was the Captain/Instructor on this course. Thank you so much for coming out to do this story and spend time with our crew. I want to make a few corrections to the story. The students were in fact on a 30 foot sprit-rigged ketch pulling boat. At night they had 45 minute anchor watch, not helm watch as we were anchored nowhere near ocean liners. The students are referred to as campers in this story. Thompson Island Outward Bound is an expeditionary learning school and it is definitely not a camp, the participants are students not campers. I am so proud of this Connecting with Courage course, and am excited that you all have the opportunity to learn a bit about what the students experience.
So many of us have this life-changing course in our hearts and our memories. I’ve taken it several times with adult women where we brought pictures of ourselves as young teens. My daughter took it twice. What a thrill to see its essence shared with your listeners. Well done.
Bravo Thompson Island Outward Bound! I worked there 17 years ago and what I saw it do for kids changed my life. I now run a program in Puget Sound aboard the historic schooner Adventuress – same powerful outcome, a new generation. How exciting! Don’t ever stop doing what you do!
Great story! Do you have other articles regarding teen mentoring?
Best regards
Well, is it a “14-foot sailboat” or a “30-foot sprit-rigged ketch pulling boat”? They can’t be living on both…