The Bupp family sits down with PEOPLE to discuss their latest adventure
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Credit: Joanna Bupp
NEED TO KNOW
- Earlier this year, Joanna and Kevin Bupp left behind their life on land to travel America’s Great Loop — a continuous, 6,000-mile journey that goes up along the east coast of the United States, through several Great Lakes, and down through several rivers into the Gulf of Mexico — via boat with their two kids
- The parents took their kids out of school, and they are now homeschooled on the water
- The family sat down with PEOPLE to discuss their latest adventure
Joanna and Kevin Bupp always had intentions to someday leave their life on land behind to travel America’s Great Loop, but they didn’t think they would do it with two young kids.
Kevin, 47, had talked to his wife about the famed boating route — a continuous, 6,000-mile journey that goes up along the east coast of the United States, through several Great Lakes, and down through several rivers into the Gulf of Mexico — for 20 years. The route is usually undertaken by retirees, not families, so the pair thought it would make sense to wait until their kids were in college before setting sail.
But earlier this year, Joanna approached Kevin with a crazy idea.
“She was like, ‘You’re the one that always says that we’re not promised tomorrow, right?’ ” Kevin tells PEOPLE in an interview. “‘The boys are old enough, and if we can get their buy-in, let’s make it happen.’ ”

Credit: Joanna Bupp
The parents decided that their kids Jackson, 12, and Julian, 10, were at good ages to trade a year of in-school instruction for homeschooling — but they wanted to make sure they agreed. Kevin says they asked their little ones how they would feel about leaving their friends and their sports teams for a year, but ultimately, they were sold by the prospect of homeschooling.
“That was my sales pitch to the boys,” Kevin says. “Right now you’ve got a two-day weekend and go to school for 7 hours a day. What if you could literally get a week’s worth of schoolwork done in a day or two and have a five-day weekend?”
“They’re already ahead of probably their peers or where their peers left off before summertime,” he adds, “so they bought into that right away, as a lot of kids would.”

Credit: Joanna Bupp
With the whole family on board, they started preparations for their big expedition.
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First, they had to find a boat — which had to accommodate their family of four, their dog and have enough space for the kids to complete their schoolwork and the parents to work remotely. That had all kinds of additional complications they hadn’t anticipated, such as insurance and certifications to operate it.
But there were also other, smaller tasks required before the Bupps left their Florida home, like figuring out how to handle their mail while they were on the water for a year.
“We thought we were gonna leave on this day — and then we had another issue and another issue. And what we came to find is that we always had an excuse not to leave the day we were supposed to leave,” Kevin says. Finally, we were like, ‘These issues will never end. There’s always gonna be something to fix. Let’s just go.’ ”

Credit: Joanna Bupp
Since they left for their trip, things have gone pretty smoothly, even if the family admits it’s no vacation.
On any given day, Joanna and Kevin are monitoring the weather and mapping their route, searching for potential obstacles in the water or points where it might get too shallow for their boat. And they’re filling their downtime with plenty of exploration of all of the towns they’ve stopped at during their journey.
“It’s not just laying around, getting a tan,” says Kevin. “There’s quite a bit more work involved.”
As for school, Joanna tapped a friend from home, who is remotely helping manage the process for her two kids — finding the right online programs for them and ensuring that they’re on track to meet their goals in every subject. And sometimes they take advantage of their unusual schooling environment for special projects, like building a boat out of recycled materials and testing it in the water.
When asked if they have recommendations for other families seeking a similar experience, the Bupps’ advice is simple.
“Don’t hold off,” says Joanna. “It’s so doable.”
Continues the mom: “Everybody’s going to have a different challenge — whether it’s work, a dog or kids. But just do the trip however you want to.”
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