Skip to main content

A year ago, an Ontario couple sold everything to sail the world

One year ago, an Ontario couple left their house and sold everything they own to sail the world.

“It was really kind of scary, backing out for the very first time,” Steve Easson said, recalling the departure from Lake Ontario with his partner of a decade, Ben Roth, on Sept. 16, 2022.

“We had no idea what we were getting into,” he told CTV News Toronto from Grenada.


The idea was planted six or seven years before they set sail from their hometown harbour in Hamilton. Easson, who had been working as a pilot for 20 years, arrived home and said, “Hey Ben, do you want to buy a sailboat?”

His colleagues had raved about the easy transition from flying to sailing, so on a whim – despite Roth telling him not to impulse buy a boat – Easson did just that and started puttering around Lake Ontario.

It was when the pandemic hit that they began considering how this hobby could become a full-time operation.

“We found a boat we could live on and then it all happened really, really fast,” Easson said. They named it “Oh Caribou” and launched a social media account to chronicle their adventures. 

Hamilton residents Steve Easson and Ben Roth have been sailing the world for a year (Supplied). Easson left his job as a pilot and pivoted to running a manufacturing company while Roth left his role at Pinterest and moved onto analytics consulting.

“We’re not wealthy by any means. We just don't have expenses like normal people have,” Easson said.

They rented out their house in Hamilton and sold their possessions on Kijiji and at garage sales, sleeping on the living room floor wrapped in blankets in the weeks before their departure.


From Hamilton, they sailed to Florida, along all of the states on the east coast before making it to the Dominican Republic, Puerto Rico, British Virgin Islands and Grenada – 15 countries and counting. They’ve spotted dolphins prancing beside their boat and sharks lurking beneath it.

Easson and Roth spot a shark while sailing (Supplied). Along the way, they added a member to their crew – Penny, a rescue dog who they adopted in the British Virgin Islands after finding her malnourished at a local shelter.

Roth typically starts looking at the weather a week or so before raising the anchor, finding a safe window to sail, and a corresponding route. “Weather dictates everything we do,” he said.

The couple adopted a rescue dog named Penny in the British Virgin Islands (Supplied). Still, they’ve navigated through “sobering” storms of 10 foot waves with close swells fiercely rocking the boat, along with an earthquake and most recently, monitoring Hurricane Lee.

In preparation for setting sail, Easson cooks enough food for the days ahead, along with refueling and servicing the boat, which is always broken. “Imagine your house on the water,” he said.

Weather dictates everything for Easson and Roth, who have visited 15 countries and counting (Supplied). It’s a pretty “regular” life at anchor once they arrive at their destination, back to eight-hour remote workdays at a little desk in the boat’s navigation station, Roth said.

But there’s also “so much freedom,” he added – waking to a glistening sea of blue, exploring in the evenings, watching sunset on the water and stars shooting across the night sky.

The "Oh Caribou" anchored at shore (Supplied).“It’s like being on vacation all the time, but it’s not because it’s your life,” Easson said. “I don't want to go back to living the traditional lifestyle, living in a house, the rat race, trying to accumulate more stuff. I just want to experience life and enjoy it and see the world.”

Next, they are aiming to cruise between Grenada and Saint Martin, and eventually, cross the Atlantic Ocean.

“I hope we can do this forever,” Easson said. Top Stories

Stay Connected