Features
How SailMaine opens Casco Bay to every kid who ever looked out at the water and wondered, “What if?”
Words by Michael MCallister
Photos Courtesy of SailMaine
Jimena’s fingers dig into Jayden’s arm as she holds on for dear life, cautiously making her way down onto the ramp—her first steps onto a dock. Every step is slightly easier than the last as she starts to gain her balance. A few waves hit the dock, and her footing goes uneasy once again. She opts to crawl into the powerboat. After several deep breaths, she says she’s ready to leave the float … for her first sail.
Later, it’s difficult to get Jimena off the boat. She waves the launch away, calling out, “Pick up the other boat first! Get us last!”
Afterwards, when she finally climbs back onto the dock, she describes her first sail the only way that felt big enough, “On a scale of one to a hundred, a hundred. On a scale of one to a thousand, a thousand. On a scale of one to a million, a million!” Moments like Jimena’s are the whole reason SailMaine exists. The nonprofit community sailing center has spent years turning Casco Bay into a classroom, a playground, and—for a surprising number of kids—the first place they ever felt truly capable.
What started as a way to get more people sailing has grown into something broader: a mission to make the water belong to everyone, regardless of ability, background, or whether a family has ever owned so much as a life jacket. Today, SailMaine runs youth summer camps, adaptive programs, school partnerships, and racing teams—all from a single set of floats where, on any given summer morning, you’ll find a remarkable cross-section of Portland heading out to sea together.
For Connor, a seventh grader who comes to sailing through SailMaine’s city programs, the appeal is simple and sincere. “I always wanted to try sailing,” he says, “but never thought I would.” Fulfilling that dream of wanting so badly to go to sea but never believing you could is exactly why SailMaine was built.
Jimena was one of the first to walk down that dock through what became SailMaine’s city sailors program, but she’s far from the last. What began as a small effort to reach kids who’ve never had a way onto the water has grown year over year, opening sailing and hands-on STEM education to students from Portland public schools at no cost to a single family. For many of them, as for Jimena, it’s their first time out on the bay—right here in their own city. The program has expanded so much that SailMaine now sends a van to pick kids up and bring them to the waterfront so that getting to the boats is never the thing that stands in the way.
Her adventure doesn’t end when the school program does. Thanks to donor support, Jimena and several other first-time sailors earned scholarships to SailMaine’s two-week summer junior camp. By the end of it, she had learned how to right a capsized boat, sail upwind on her own, and master tying a bowline—all while making new friends and, most notably, building a kind of confidence that doesn’t wash off when the life jacket comes off.
Parents see the progress and confidence before the kids can name it. One mother plainly describes it, saying, “The change in my son during the two weeks he participated in sail camp was nothing more than monumental. I now look at him and know there are no boundaries to what he can do.”
That sentence is the quiet thesis of everything SailMaine does, and nowhere is it more literal than on the water. On Mondays, as Jimena walks down to the floats, she falls in alongside Randy and Sara, two of SailMaine’s visually impaired adaptive sailors, while a crew of volunteers help get everyone rigged and out on the water. Adaptive sailing isn’t a separate track tucked off to the side here; it happens on the same docks, in the same fleet, in the same salt air as everyone else.
The mix only gets richer midweek. On Tuesdays and Wednesdays, coming in for lunch, Jimena sits at a picnic table with kids from SailMaine’s partner programs at Portland Community Squash and the Boys and Girls Club.
Then, there are the days that become the stories kids tell for years. On the last Friday of her program, Jimena sails out with her friends all the way to Peaks Island, where they split ice cream cones before finishing the afternoon with a swim off the docks back at SailMaine. It’s the kind of ordinary-magic day that most Maine kids assume belongs to other families—and that SailMaine insists belongs to everyone.
Ask anyone who has watched a first-time sailor cross from white-knuckling the dock to steering their own boat home, and they’ll tell you the lesson was never really about wind or rigging. It’s about a kid discovering that the thing they were sure they’d never get to do is suddenly, thrillingly, theirs.
None of it runs on saltwater and good intentions alone. The scholarships, the adaptive equipment, the volunteer training, the van that brings kids to the dock—all of it depends on a community that believes access to the water shouldn’t be a privilege. Every donation expands the dock.
Jimena knows it before any of the adults can explain it. “One to a million,” she says. “A million.”
To learn more about SailMaine’s programs, scholarships, and how to get involved, visit sailmaine.org