The Vineyard has a new nonprofit founded on a simple conviction: Children learn best when the world itself is the classroom.
The Wonder and Wander Collective, a 501(c)(3) nonprofit, is launching an immersive, nature-based education program centered on Life Goes On, a 54-foot, Robert Perry–designed bluewater ketch. Donated in 2025 and sailed up from the Bahamas to Edgartown Harbor, the vessel now serves as both classroom and expedition platform for young learners.
This summer marks the group’s pilot season, with its first crew of young sailors heading out on the water. Geared toward children ages 8 to 14, the program emphasizes hands-on, experiential education. Wonder and Wander is designed as a homeschool- and family-centered program, serving kids who are learning outside the traditional school structure.
Kyleen Keenan is a steward of the nonprofit, along with Nico Ewing, Rachel Ewing, Ariana Binney, and Capt. Kate Richardson. Richardson and Keenan are living on Life Goes On in Edgartown Harbor together this summer, along with Francesca (“Frankie”) Vignolo-Keenan, Keenan’s 11-year-old daughter.
“Community is the medicine we all need,” said Keenan. “I think it matters more than ever that we have safe and inspiring spaces for young people to come together and to do things that bond us in community.”
Keenan grew up landlocked in Western Massachusetts, but learned to sail early alongside her father, who would buy and restore old sailboats, and who restored Life Goes On and donated it to the nonprofit in 2025. Together they explored the many islands of New England, including Martha’s Vineyard. When she turned 18, she moved to the Island and began working as a waitress.
“Success to me is more children to get out on the water, and more children falling in love with the devotion, the art of sailing, and being in community,” said Keenan, “and a full programming next year, families and children being able to connect in this way, offscreen, in immersive, nature-based learning.”
A female captain and woman-led crew guide the program, bringing both maritime experience and mentorship to the next generation. Capt. Richardson, U.S. Navy veteran turned professional mariner with a 100-Ton Captain’s License (officially a Master 100 Gross Tons), which requires 720 days of sea service and passing rigorous written exams, said the environment on the water offers something unique.
“What a great experience to learn at 10 years old, and these kids are Island kids, they can
captain boats with these skills,” said Richardson.
Richardson began her maritime career working on the fast ferry between Martha’s Vineyard and Rhode Island while studying marine biology in college. She sees wind and current as teachers, constant forces that she is not there to control but rather to work with. Richardson also highlights the power of music, and plans to incorporate that into the Wonder and Wander programming.
“There’s something really special about singing together and harmonizing and doing it on the water,” said Richardson, “to be out here where the ocean really amplifies anything you’re feeling and doing.”
Their first children’s retreat is scheduled for August 24, and will be five days of sailing, swimming, and singing. Geared toward young girls but open to all children, the program will start with guests coming aboard on Monday and getting to know the boat, followed by a small sail on Tuesday, a bigger sail on Wednesday, and an overnight voyage on Thursday. The weeklong experience will be offered on a sliding scale, from free to $700, to meet families where they are, and offer the experience to all interested children. It will be held two weeks in a row.
“I also understand that this is like a luxury to be able to world-school our kids,” said Keenan. “That’s why we wanted to make a fundraiser. If people donate, we can be on a sliding scale so if you can’t afford it, you can still come, because there is abundance.”
The organization will host an “Evening on the Water” fundraiser on August 23 at Gannon and Benjamin Marine Railway in Vineyard Haven. The event will feature live music, a children’s song performance, mocktails served by young crew members, local food, a silent auction, and tours of Life Goes On. Charters aboard Life Goes On will also help sustain the boat and fund sailing scholarships, so that a child’s access to the water will not depend on what their family can pay.
It is the organization’s foundational belief that children who learn this way become more confident, more capable, and more connected to the sea, to new places, to people, and to a sense of their own competence.
“We’re meant to learn by play that keeps us curious, and that makes us geniuses,” said Keenan. “When you’re out there and you’re learning by doing, you’re learning math, you’re learning physics, you’re learning, and you’re in this natural environment, and I feel like that’s what the children of the future need.”
Although similar to Sail MV, another Island non-profit that provides sailing lessons and maritime education to local youth, Wonder & Wander focuses not only on learning to sail but also the collaborative dedication and effort that comes with being part of a small crew.
The program is also intentionally community-driven. “It’s an asset held in the community,” Keenan said. “There is a movement toward putting land and assets in community hands, and that’s the goal of this. To have this be something that evolves beyond us, and whoever wants to get involved, it can be managed by the community for the betterment of the community. I think decentralizing assets in that way, it’s like instead of everything being mine or yours, it’s for all shared use.”
Keenan sends her daughter Frankie to the Woods School, which is a nature-based homeschool program at Allen Farm based on the same foundations that guide the nonprofit. Keenan says living with an 11-year-old child, she sees firsthand the lack of curiosity and wonder in today’s youth. “My hope is through these intimate programs, especially for young women, that they can feel confident, like seeing a female captain, and saying, Yeah, things are gonna go wrong and we can fix them, and we can do hard things, and we can get through this, and living in community we’re happier.”
The hope is that summer sailing becomes one piece of a year-round experiential education model that extends into international field programs. Working with partners around the world, students would be brought into new ecosystems and communities to study, contribute, and broaden their sense of what’s possible.
“Loneliness is an epidemic that many of us suffer in silence,” said Keenan, “but when you are out on the water and it’s six girls, and we’re singing, and we’re sailing, and we’re swimming and we’re being present, and we’re really holding space … I think that that’s a powerful medicine for each other. We all need it.”
