Fifty years after a young Che Guevara crossed South America on the back of a motorcycle nicknamed La Poderosa (The Mighty One), a Canadian decided to traverse Africa on a Chinese-made scooter nicknamed Anne Murray.

The Alberta-born Brendan Van Son, 29, is a travel enthusiast, photographer and social media entrepreneur who provides travel advice, hostel booking information as well as his own humour-laced adventure stories on his website brendansadventures.com. He even gave up a job in Canada to pursue his dream of full-time travel over the last four years.

Once arriving on the shores of Africa, in Morocco, from Spain and before that, Latin America, Van Son was attracted to the idea of solitary travel. He had no plan, but knew he wanted to get off the beaten path. He decided to forego the big tourist overland routes and game parks to make his own way across this vast continent in the spirit of other seasoned travelers who came before him. But Van Son had something else in mind, wanting to do something completely different from his previous backpacking excursions in Europe and South America.

The first six months in Africa were the toughest as he headed through some unimaginably rough terrain, namely the Sahara desert. By the time he made it to Bamako, Mali, en route to the ancient city of Timbuktu, he was held up by advancing rebels and looming French air strikes and began to feel worn down. On a whim, he decided to buy a fire-engine red scooter and take the long way down on an impromptu road trip.

“When I got to Mali I was already sick of public transport. I saw some scooters from the window of my taxi,” he said. “I asked the driver how much they cost and decided on the spot to buy one. It was very spur-of-the-moment actually.”

Like a 2.0 version of the Cuban revolutionary, Van Son held a naming ceremony for his scooter via social media. His Twitter and Facebook accounts were bombarded with potential names paying homage to his nationality. Pamela Anderson, Rita MacNeil and Anne Murray were his top three choices.

“What can I say? The response was overwhelming. It was destiny that I would choose Anne Murray and ride her all the way to Cape Town,” he said with a laugh. “The thought did cross my mind how odd it would be for Murray, who may suddenly see her name trending as a hashtag on Twitter.”

The intrepid traveller chose Cape Town as his end destination in a very Paul Theroux-type fashion. But instead of the Cairo-to-Cape Town itinerary attempted by many before him, Van Son took the route less travelled from West to Central and South Africa, and shared his experience every step of the way online.

“It was such a roller-coaster ride. At the start it was really easy. From Mali to Burkina Faso and Ghana things were going smooth. Then in Togo I got malaria,” he said. “I got to Cameroon and crashed my bike. I got to DR Congo and got malaria again.”

Like Graham Greene many years before him, Van Son did his entire journey without maps. Rather than GPS, he relied on good old-fashioned “LPS” — something Africans call local positioning system, in which you ask a few people for directions, and go with the most popular response.