Where the hell is Jonathan B. Roy?

Morocco, Albania, Slovenia and Italy so far. Georgia then, then Cyprus and…

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Where would you go if you could live anywhere in the world for free?

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A Left Bank apartment in Paris? Somewhere overlooking Bondi Beach in Sydney? The cap? Copenhagen? California?

Jonathan B. Roy can make that decision. The 36-year-old from The Original is one of 12 people chosen to live for free for a year in Airbnb accommodation.

“Every day I have to pinch myself,” Roy says in a video call from Madonna di Campiglio, a ski village in the Italian Alps. “It’s not something I could afford to do myself.”

His journey began in October in Marrakech, Morocco, and continued through Albania and Slovenia. He and his partner, Gabrielle Rouleau, will stay 10 days in Italy before heading to Georgia, the former Soviet republic, then to the island of Cyprus in the Mediterranean.

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Off-the-beaten-path destinations are perfect for the veteran off-the-beaten-path traveler.

Jonathan B Roy and his partner, Gabrielle Rouleau, at Tirana airport, capital of Albania.
Jonathan B Roy and his partner, Gabrielle Rouleau, at Tirana airport, capital of Albania. Photo by Jonathan B Roy /instagram

“The highlight was Albania,” he said. “Everything was so fascinating. Each year of their history is rich. Everyone is happy to talk and tell stories. The literature, the food, the landscape… Everything is really good.

“I didn’t know anything about Albania and that’s why I didn’t want to go to Paris. I know the Parisian culture. I want to go somewhere where I can learn.

Roy entered the Airbnb contest last June when he was back in Canada after a four-year, 40,000 kilometer cycling trip around the world was cut short by the COVID-19 pandemic. He entered on a lark, one of 314,000 people to answer Airbnb’s question: “Why should we choose you to live the nomadic lifestyle?” Next, she was asked to submit a short video and then do a follow-up phone interview.

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Roy has degrees in engineering and law, but plans to travel and tell stories as his full-time jobs. He uses Instagram, Facebook and Youtube accounts to bring his followers on the journey. Abroad, he was able to continue doing some of the website, writing, and video work he had in Canada. Rouleau, a lawyer, works one day a week during the trip.

Another highlight of the trip: Slovenia. The small country of two million people straddles the Balkans and the rest of Europe and traces its history through the former Communist Yugoslavia to the Austro-Hungarian Empire.

“I thought five weeks would be enough to visit Slovenia because it’s so small, but I could have stayed there for six months,” Roy said. “It’s a gem. He has everything.

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The contest rules stipulate that the couple must stay a minimum of four weeks in each rental unit. This has made it easier to be safe during the pandemic, he said. On his bike trip, Roy frequently ate and slept with people he met along the way. This year, they live like locals.

“I probably wouldn’t be traveling if I wasn’t on this program,” he said. “But most of our activities take place outdoors. We are alone in our apartment. We don’t travel much and when we do we rent a car. I have adapted my way of traveling.

But the new journey has its own challenges.

“On my bike, I was traveling with 120 pounds, including my bike,” he said. “I thought now that I had a suitcase it would be easier. But it’s 10 times worse! We have skis. We have boots. We have helmets. We have all these books. We even have a carpet we bought in Morocco…”

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Roy was planning to use this time to write a book, a sequel to his first Sleeping Out Story, about his biking epic. But writing and travel have not been easy companions.

“After Albania, I try to find less interesting countries,” he laughs. “My goal this year is to finish my second book, but in Albania I didn’t find the time or the will to write it. Everything was so fascinating. I was learning too much about what was going on and I don’t didn’t finish my chapters!

The couple are due to return to Canada in July.

The amazing Predjama Castle in Slovenia.  It began to be built in the 13th century, directly on a massive rock face and under an overhanging protective stone.  Its best-known owner, Erasmus of Lueg, took refuge there in the 15th century after having killed in a duel a relative of Frederick III, Emperor of the Holy Roman Empire.  Legend has it that one of his men betrayed him, signaling the time when Erasmus was at the outhouse, the only place separate from the fortress and seen to the left of the castle in the photo.  A well-placed cannon shot wins.  Photo courtesy of Instagram/ @jonathanbroy
The amazing Predjama Castle in Slovenia. It began to be built in the 13th century, directly on a massive rock face and under an overhanging protective stone. Its best-known owner, Erasmus of Lueg, took refuge there in the 15th century after having killed in a duel a relative of Frederick III, Emperor of the Holy Roman Empire. Legend has it that one of his men betrayed him, signaling the time when Erasmus was at the outhouse, the only place separate from the fortress and seen to the left of the castle in the photo. A well-placed cannon shot wins. Photo courtesy of Instagram/ @jonathanbroy Photo by Jonathan B. Roy /instagram

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