Funded Partner Spotlight: SailFuture

Apr 30, 2024News
SailFuture students on a boat

Ten years ago, SailFuture Co-Founder and CEO Mike Long was a student at New College of Florida when his former high school principal, who had expelled him, reached out with an invitation.

“I was really lucky to be where I was at in my life based on the choices I had made when I was a kid,” he explained, and his former principal knew that. “She said, hey, will you come talk to a group of kids we’re on the verge of expelling?”

Long was living on a sailboat at the time. He figured going out on the water with the kids might be better than just meeting at the school where they weren’t currently thriving.

“Out on the boat, all of the weirdness of having someone talk to you about your life disappeared,” Long said.

After that initial trip, the kids asked if they could come back the next week. So they did. And then they returned the week after that, and the week after that.

“Over my years at New College, it evolved into a thing. We’d take a college kid who was fairly privileged at that point in their life, pair them with a high school kid struggling with barriers to stability, and put them on a boat together,” Long explained. “The idea was that sailing can help people build relationships that have meaning and value. It can accelerate trust, and let you use play as a way to come together.”

After college, Long went off to Washington, D.C., where he worked in the policy world – and hated it. He found himself missing his afternoons with the kids. Those interactions ultimately felt more meaningful and valuable than the policy work he was doing, so he returned to Florida and the nonprofit world full-time.

At first, he worked with judges who were frustrated with the high recidivism rates they saw after sending kids to juvenile jails and prisons.

“Sentences that were supposed to be rehabilitative were just not working, so some of the judges were open to the idea that we could put kids out on a boat, take them out of the country, promote community safety, and also make it less likely that these kids would offend,” Long explained.

What he found was that while things went fairly well when they were out on the boat together doing service projects, too many kids from the program still ended up passing away or reoffending within a year of being home. Taking a different tack, he decided to open a group home for struggling kids in Pinellas Point.

“The neighbors were not so excited about us moving there,” he said. “I learned what NIMBYism looked like in practice.”

The home, he said, was the “missing piece” that helped kids make the transition out of juvenile detention. They offered wrap-around services like schooling, therapy and job training, and continued to use multi-week sailing trips as a way to build skills, community, and connections between participants.

Prompted by their success, they soon opened another group home before taking a break to think more strategically about how their nonprofit could and should evolve.

“We needed to figure out what we were uniquely good at and what was manageable for growth, and we landed on a school, not just reinventing what’s already out there but thinking about what high school could and should look like for kids having a hard time engaging in it,” Long explained.

In 2021, they opened SailFuture in the historic Norwood School.

“We had the opportunity to quite literally create whatever we thought was going to be best for disengaged learners… and the major thing that came out was that this should feel more like the real world,” Long said. “It shouldn’t be that kids go to school five days a week for four years and then go out into the real world and have no idea how to be an adult, no idea how to file taxes, no preparation for any specific job, no introduction to real world norms and expectations.”

Working backwards from that “real world” goal, they created the Pathways Program, which is supported by a $250,000 programmatic operations grant the Foundation and Orlando Health Bayfront Hospital. Starting in eighth grade, SailFuture students begin going on weekly or bimonthly tours of local businesses to gain exposure to future career possibilities and start thinking about the kind of work they might enjoy doing and be good at. By 10th grade, students go out and do mini consultancies with local business owners, coming up with potential solutions to challenges local businesses are facing. In 11th and 12trh grades, they’re out working in those businesses, rotating through five different internship pathways two days a week.

“We try to place them in diverse and different businesses. The idea is that, even if you think you know what you want to do, you’re experiencing a lot of different things to confirm that,” Long said. “During their final year at school, they do a year-long placement, getting trained in a specific skill set that will prepare them for a job. When they graduate, hopefully they’re making $20-$25 an hour working for someone they’ve already worked for, who’s a good cultural fit, and they’re ready to start work on day one.”

The school also offers an integrated mental health program with an on-site therapist as well as group adventure therapy – like kayaking trips to Weedon Island – that help kids build trusting and deeper relationships. And all SailFuture students spend seven to eight weeks sailing around the world on a boat, doing service projects in different countries. The average trip is roughly 2,000 miles long and represents a mandatory right-of-passage and graduation requirement for the school.

“They all work in defined crew roles learning skills that can be credentialed if they want to move into that industry at a high level if they want that,” Long said.

The school will graduate its first class of students next year, marking a pivotal moment in the SailFuture’s trajectory.

During the 2024-25 school year, SailFuture is expected to have between 80 and 90 students. While a handful of families pay a sliding scale of tuition, 95% are on full scholarship with an average family income of about $23,000 a year for a family of four.

“Serving those families facing the most barriers is important to us,” Long explained.

SailFuture is always looking for more local businesses to participate in their internship and job training programs, which they are able to fund with due to their partnership with CareerSource Pinellas. To learn more or get connected, SailFuture, visit

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