Benn and Charlotte Wood were whizzing through the Gulf Stream in a boat they had just bought, and piled their kids onto, when they started to worry they were in too deep.

“We were leaving America and both Benn and I were throwing up off the back of the boat and there was a moment where we thought, what have we done?” Charlotte recalled.

It had been just over a year since the Ontario couple, who owns an information technology company, stumbled upon YouTube videos of families that embarked on adventures to far-flung locations.

They realized that was an itch they needed to scratch too and so within months they pulled their kids, 14-year-old Bella, 13-year-old Oscar and 10-year-old Jasper, out of school, sold their Thornton, Ont. home and packed everything they thought they needed for a year into a van.

They had an ambitious plan: buy a boat and spend the year sailing from Florida to the Caribbean, giving the kids an experience unlike anything they’d get in a classroom.

Benn had sailed as a teen but not much as an adult, neither he nor Charlotte had any experience homeschooling, and no one in the family knew much about the Caribbean, so they relied on the internet for advice.

“It wasn’t like we blazed a trail or completely broke the mold doing it,” Benn said. “We just copied what a niche of people out there are doing because we figured it was worth a go.”

There were sentimental reasons for the trip too.

“A year or so before, we lost Benn’s dad. He was 53 and fit and well, but he had a massive heart attack,” said Charlotte. “That really brought the perspective that… we have no control over how long we have. We really started to think about if we wait until we retire or until the kids leave home, we could be waiting for nothing.”

Their search for a boat began around November 2016, but dragged on long after they sold their house and headed to Florida in January 2017. Eventually, time on their U.S. visas started to run out, so they nabbed a boat, but had to sail away in March 2017 before doing any training.

They did however muster time for a ceremony to celebrate the boat’s new name “Jay’s Nest,” a nod to the family’s diehard love of the Toronto Blue Jays.

“We got all dressed up in our Blue Jays gear, took a bunch of pictures and had a big, old Blue Jays flag fly off the back of it too,” Benn recalled.

It was a fitting start to the trip for a family with a reputation for “hare-brained schemes,” as Benn calls them. The Wood family moved to Canada from England ten years ago without knowing a soul.

Once here, they kept up their daring streak by once pulling the kids out of school to trek down to Dunedin, Florida for the Jay’s spring training camp. One season a few years back they painted a José Bautista beard on Oscar and eye black a la Troy Tulowitzki on Jasper, turning the kids into viral sensations when Benn posted a video of Oscar online pretending to hit one of Bautista’s famed home runs.

“When you’re married to Benn you just get used to stuff like that,” Charlotte said, laughing.

It took no convincing to get her and the kids to journey to the Caribbean, though Oscar admits there was one downfall.

“Whenever we got internet, if there was a Blue Jays game on, we tried to watch it, but we didn’t get to see much,” he said.

He was, however, ecstatic to fish, and Bella and Jasper were equally happy exploring the coral reefs.

But before they donned snorkeling gear or cast a rod, there was work to be done. Charlotte and Benn put the kids on a strict school schedule, that was even tougher than what they might have faced if they stayed home.

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The kids didn’t get any time off for summer vacations, weekends or Christmas break. Every morning started with hours of lessons, cobbled together from resources they discovered from around the world and advice from the kids’ teachers.

“It was great doing school on the boat because there was no noise,” Jasper said. “You can ask your parents a question as soon as possible because you don’t have to wait for a teacher.”

It’s hard to tell how many families take their kids out of school for adventures like the Wood family’s.

Statistics Canada data shows 8,754 students were homeschooled in Ontario in the 2016-2017 school year. That number has been steadily climbing from 5,679 in 2012-2013.

“There’s no database keeping track of what each homeschooling family’s reasons and methods are, nor anything else about their lives, so we have no statistics on how many are travelling,” Marian Buchanan, an Ontario Federation of Teaching Parents spokesperson, said in an email.

“I know a few homeschoolers who have travelled during their homeschooling years, but that wasn’t why they started homeschooling, and they didn’t stop homeschooling just because they stopped travelling.”

“Road-schooling” or “world-schooling” often involves adapting to a new location while figuring out how to juggle parenting and teaching.

Boating adds extra struggles; it’s not always smooth sailing. Wi-Fi can be difficult to get on open waters, sometimes seasickness wreaks havoc on plans or in the case of the Wood family, you run into big trouble like Hurricane Irma.

When the family learned Hurricane Irma was headed their way in August, they parked the boat in a Turks and Caicos shipyard and departed for Benn’s mom’s UK home. It was good thinking. Irma became the fifth-costliest hurricane to hit the U.S. mainland and caused an estimated $50 billion in damage, according to the National Hurricane Center.

“We didn’t expect the boat to be knocked down and destroyed,” said Benn. “It wasn’t completely turned to matchsticks, but it was...busted up inside.”

Meanwhile, the adventure continued in England.

“I kind of felt bad,” said Bella. “We were meant to be staying for only a month, but we ended up staying for six.”

That meant sightseeing at more than 30 castles, including the famed Highclere Castle where Downton Abbey was shot, renting an RV for exploring and spending plenty of time with grandma.

Eventually it was time to say goodbye. The family returned to Ontario in March 2018, found another Thornton home and the kids re-enrolled in school.

To Benn and Charlotte’s relief, the kids “hadn’t skipped a beat” and “were ahead in some subjects.” Bella quickly made honour roll and the boys got good report cards.

But the family’s wanderlust wasn’t gone. They started toying with taking a European road trip or journeying across Australia and New Zealand.

Then, this past July, they edged towards a plan. Benn headed to Florida to look at another boat, telling the Star, “We will be less naive and starry-eyed, but have a proper crack at it again.”