Some people seem to have been born on a bike, and others seem born to bike. Chris Winter is both.

In conversation with the Georgia Straight, the Whistler-based cycle-tour operator recalled how, when he was a toddler, his parents, Mike and Linda Winter, took him to England and Wales in the early 1970s. “My parents pioneered bringing North American riders to Europe. I’m a rare second-generation bike-tour operator.”

In a Whistler cabin with their son, Mike and Linda weighed in with memories of their own. “We got the crazy idea while chaperoning high-school students on a bus tour in Holland in 1970,” said Linda, whose husband was an Ottawa English teacher. “One day we rented bikes to explore the Apeldoorn forest, and it turned out to be a much more in-depth experience than on a bus. The next year, we put together a bike trip to the Rhine. Only three students enrolled. Mike tried harder, putting up signs at the entrance to school cafeterias and giving lunch talks. He recruited 18 kids.”

Mike recalled the price: $350, including airfare. “In those days, only students were interested. Adults wouldn’t be caught dead on a bike,” he said. “We rode 10-speed Peugeot bikes with drop handlebars, toe clips, and outfitted the kids with Jofa hockey helmets, as there were no bike helmets back then.”

Linda remembered European children reacted to the bizarre sight by throwing stones. “Two years later, I got a letter from one girl—who by then was in university—thanking us for the character-building lessons on coping with the hilly conditions in England and Wales. We just imagined it would be flat. It was anything but.”

Those were the years before Google Earth. “When my parents started, there weren’t even fax machines,” Chris said. Linda added: “All we had were Teletypes.”

By 1985, adults began to sign on as well. “That was the last year we camped or stayed in youth hostels. From then on, it was hotels,” said Linda, who currently acts as an adviser to Cycleventures, the company the Winters founded in 1972 and ran for three decades before Chris took charge. In Chris’s eyes, his mother still holds the reins. “The clientele have returned time and again for 30 years. Mom has a following like you wouldn’t believe.” An older brother, Sean, a secondary-school teacher in Vancouver, also guides with the company during the summer.

As well as taking on responsibility for Cycleventures, Chris, who moved to Whistler in 2002, simultaneously launched a mountain-bike touring company, Big Mountain Bike Adventures. “Whistler did it to me,” he said. “This is where I got the bug. My first branch off from Cycleventures was in Switzerland. A bit like when my parents started, back then it was a far-flung adventure to take mountain bikers to Europe. Twelve years later, it’s finally catching on with riders who’ve spent years at Moab [Utah] and are game to try something farther afield. Whereas my parents—who have ridden every back road in France—focused on Europe, with my new venture we go to Third World and developing countries.”

Asked how mountain bikers differ from road cyclists, Chris said that fat-tire riding is quite specific to each individual’s comfort level. “They tend to be hard-core cyclists who typically own several different types of bikes. Demographically, there’s an 80-20 blend of male and female, with a good mix of couples and singles on our trips.” Whereas Iceland is among Chris’s new favourites, his father pointed to Scotland as his first choice. As for Linda, the Alsace and Black Forest regions of France and Germany, respectively, keep calling her back. All three agreed that France, Italy, and Spain are by far the most cycle-friendly locales.

When the Straight met up with Robbin McKinney at his office in Fairview Slopes, the long-time cycle-tour operator agreed with the Winters’ assessment that Europe remains the most popular choice with North American cyclists. “Provence is where I first began in 1997 with my own company, Great Explorations. It remains the best place for families in search of food and culture. It hits everything on the list. My kids are seven and nine, and we cycled with them there last year on ride-along bikes. I can’t wait to take them on the Camino [de Santiago] when they’re a little older.”

Much like Chris Winter—whose four-year-old daughter, Ella, pedalled her own bike on a multigenerational family outing in France last summer—McKinney said that determining how soon a child is ready to cycle-tour depends more on the parents than the offspring. “Choose appropriately,” he counselled. “Bike paths in the Loire Valley, for example, are mostly level and separated from motor traffic. We just had a reservation from a family who want to ride the Canadian Rockies with their 13- and 15-year-olds.”

Have websites that help people plan their own tours had any effects on business? McKinney said they’re both a threat and an opportunity. “People still value that someone like me, who has been guiding since 1985, has designed routes for cyclists who value culture over simply riding from point to point like GranFondo types. Our groups are more about a relaxed adventure. Behind-the-scenes support is the attraction of my other company, Randonnée Tours. Clients choose their own dates and save money by being self-guided. We tailor trips to their individual needs, plus supply comfy bikes.”

Bikes are personal. Most cyclists relate to theirs like a favourite pair of shoes. A comfortable fit matters most. When asked about choosing equipment to pack on a cycle tour, Trish Sare, director of BikeHike Adventures, listed helmets, clipless pedals (for those who wear bike shoes), and seats. When interviewed at her Granville Island office, Sare, who’s guided trips for 20 years, said that Costa Rica has been her company’s bread and butter from the start. “We mountain-bike 40 to 50 kilometres a day on rugged roads—but not North Shore rugged,” she said. “We’re not all about biking, because people who go with us are older, so we add…hiking and horseback riding to the mix.”

Perennially popular “bucket list” destinations with BikeHike’s clients include the Galápagos and Ecuador. “This year especially, it’s Cuba,” she said. “Every second call we’re fielding these days is someone, particularly Canadians, who wants to see Cuba before the country changes. I’ve been leading trips there for three years now. We ride mountain bikes fitted with semislick tires. Cuban roads are in not bad shape compared to dirt-and-rock trails in some countries we visit. The countryside is more hilly than mountainous. Cuba is about the people, not wildlife.” Besides Cuba, Sare pointed to Slovenia (“It’s finally taking off”), as well as Vietnam and Morocco. “People rave about Morocco. It’s our most culturally authentic trip, as we follow nomads on their annual migration. We are their guests.”

No matter where, McKinney summed up cycle touring’s enduring appeal: “We’re all after the same thing—wind in our hair and biking through exotic places.”