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Insider’s Guide to Walking Trips

Tyler Dillon | October 4, 2016

The insider advice on this page is from Wendy’s Trusted Travel Expert for bike trips and walking trips: Tyler Dillon of Butterfield & Robinson.

Trusted Travel Expert
Tyler Dillon

It was while living in Asia that Tyler learned the joys of traveling by bike or on foot: seeing a new place at slow speed, stopping whenever you please, no tour-bus windows between you and the locals, smelling the markets you pass by—in sum, having a real experience of a destination. After transitioning from English teacher to bike-tour guide, Tyler lived out of a suitcase for five years, hopping between cycling seasons in Asia, South America, and Europe. He now designs private biking, walking, and hiking trips from B&R’s headquarters in Toronto but still hits the road every few months, scouting the perfect combination of reasonable biking or walking distances between sights (his trips are more about getting a sense of place than burning through miles), lightly trafficked roads and trails, and the best rooms in the most interesting hotels. His trips range from lodge-to-lodge treks in the Alps to gentle tramps through the English countryside to bike loops around iconic wine regions. He takes care of all the logistics and, for travelers who prefer not to have a guide along, will provide a GPS pre-loaded with each day’s route (including stops where you’ll be welcomed into a private home for a cup of tea, or to meet with a local artisan). For those who want a private guide, Tyler seeks out not professional guides or expert cyclists, but creative types who light up a room; often he finds them working at local NGOs.

Travel arrangements start at $500 per person per day, not including airfare.
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Key info about walking trips

Wilderness vs. Civilization
The places that make for an amazing walking destination generally fall into three categories. Those that are very remote and empty, such as Patagonia and, Newfoundland, are ideal for travelers who want to disconnect and be surrounded by vast nature and wide landscapes; those that are full of small villages and markets, such as Oxfordshire, are better if you want to be immersed in a culture while you walk alongside the locals through rural landscapes. Some places—Peru and Bhutan, for instance—are a lovely combination of wilderness and civilization.

Walking vs. Hiking
For me, there’s no clear distinction between walking and hiking. Maybe it has to do with how much uphill is required; maybe it’s about whether you can bail out midday and call a taxi to come meet you. Generally, walking trips tend to happen in the “civilized” places where you meander through fields, and hiking happens in the “wilderness,” where the activity is an end in itself, albeit in a lovely natural setting. Walking trips typically cover about four to five miles a day, hiking more like seven to nine miles.

Making life easier
The vast majority of trips I arrange are led by guides, though in some places where the trail system is obvious—such as Oxfordshire or Burgundy—we can send GPS routes to your phone and indicate good places to stop along the way. We move your luggage from hotel to hotel, either by car or porter, so all you’re carrying is your camera, water, snacks, and a rain jacket. I don’t ever want anyone to sweat too much. Glisten, yes. But not sweat.

Where to Walk

Iceland walking trips

Walking trips in Iceland are great due to the novelty of the geography. Photo: Butterfield and Robinson

Best place for walking
Iceland. The walking is great here due to the novelty of the geography—remote and dramatic expanses, isolated valleys, fields of moss that are three feet deep and bouncy like a trampoline (you can actually jump off cliffs onto them), active volcanoes, and magnificent waterfalls. Gnomes are a near-religious figure here—they exist, according to many Icelandic people—so there’s a bit of magic in the air too.

Best bang for your buck
Portugal. It has all the appeal of other European countries, but for a fraction of the cost. The cities are packed full of things to do, all with entrance fees of less than $15. For great walking, head to the Douro Valley, home to the famous Port wine and one of the most dramatically beautiful landscapes in all of Europe: Terraced vineyards tumble down to the water as the Douro River cuts its serpentine course to the Atlantic. Around every bend sits a graceful riverside village.

hiking in the Dolomites, Italy

A hiking trip through Italy’s Dolomites is ideal for any age. Photo: Butterfield and Robinson

Best walking trip for families
The Dolomites. These stunning peaks have drawn mountaineers for centuries, yet somehow they remain one of Italy’s best-kept secrets. The area is also full of diverse offerings for all age groups—from amazing hikes and horseback riding, to rock climbing and learning about the mountains’ geology and history, there are plenty of options for kids and adults alike.

Best walking trip for solo travelers
Bhutan. Walking through this isolated kingdom often becomes a life-altering pilgrimage. There were no roads in the country until the 1960s—even today there really are only two—so it’s truly a walking culture. Stop in at cliff-side monasteries overlooking valleys, sip tea with the locals, take part in prayer ceremonies—and that’s just Day One. I love sending solo travelers here because the culture truly values pilgrims, and while it’s plenty exotic, it’s also quite safe—and full of English speakers who can help you if you get lost. The trail options here are overwhelming, but I can steer you to the path that leads to an 800-year-old monastery rather than to the village dump.

Best walking trip for adrenaline junkies
Patagonia. Here, it’s all about vast open spaces and trying to explore as much as possible. Not only is the hiking spectacular, but this region is also chock full of adventure: trekking volcanoes, climbing glaciers, biking valleys, horseback riding toward what feels like the edge of the earth…. There’s nothing like a proper asado (a kind of Argentine barbecue) with real gauchos right on the trail, instead of the touristy affairs that local hotels set up in their backyards.

hiking Patagonia

Walking through Patagonia is all about vast open spaces and trying to explore as much as possible. Photo: Butterfield and Robinson

Bragging Rights

We have many ties to the local communities in Newfoundland, where there is a big tradition of parties in churches, community centers, and private homes. These can be inaccessible to the typical traveler, but as soon as you have an “in,” the people are as warm and welcoming as a 50-year-old quilt. After a day of walking the island’s vast and scenic trails on an itinerary that I arrange, you’ll arrive at an unforgettable tilting parish-hall kitchen party, complete with musicians playing the spoons, fantastic homemade food and moonshine, and a whole new set of friends.

Places Best Seen by Foot

Peru. Many people are under the mistaken impression that there is just one “Inca Trail.” There are, in fact, a million of them crisscrossing the country—but only one that you’ll be charged to share with 500 backpackers every night. I can guide you to equally beautiful but far less crowded trails that the Incas blazed centuries ago, and that their descendants still use today. Since the Incas’ pack animals (llamas and alpacas) could navigate stairs, they built cobblestone trails that run straight up and down mountains; in Europe, the paths were switchbacked to accommodate horses. There is something spiritual and transcendent about climbing these ridiculously beautiful staircases through cloud forests and walking amid the ancient ruins of the Sacred Valley. Unwinding with a pisco sour at dusk after a picnic on top of the world? That’s not bad either.

Newfoundland, Canada. Hiking on this island truly feels like you’re in another world (even though you’re not too far from the U.S. border). You see wide expanses of raw and stark nature, from ranging moose to towering icebergs, and windswept views that span for miles. You’ll also encounter Newfoundlanders’ legendary hospitality and preservation of a traditional way of life. A typical day might include stops at a codfisherman’s home and an abandoned church-turned-artist’s studio.

Oxfordshire, England. You’ll feel like you’re walking through a J.R.R. Tolkien book, with quaint villages of honey-colored stone cottages and trails that lead you through forests, meadows, and even locals’ backyards (though if you arrange the trip yourself without knowing the area well, you could end up on a trail that dumps you in the back of an industrial park, and you’d miss the best parts of Oxford University’s maze-like campus). Best of all, there are pubs just about every six miles: Right when you feel like you’re in the wilderness but it sure would be nice to have a pint, you come around a corner and there’s a little thatch-roofed hut with a fire in the fireplace and homemade beer on tap. The English call this tramping—a meandering walk that feels mildly illicit (thanks to the right-of-way laws that let trails run through private property), with booze involved. If you’re in the mood for something a bit more refined, we know an aristocratic couple who will welcome you into their palatial estate for tea, and we have friends who can get you into Oxford’s private clubs.

Most Overrated Walking Routes

Despite the picturesque beauty that surrounds it, Cinque Terre has become very touristy and gets busy extremely quickly, especially during high season.

Biggest Rookie Mistake

There’s no faster way to ruin an amazing hike than with an uncomfortable pair of brand-new shoes. They might look great, claim to have perfect arch support, and feel terrific in the store, but either break them in before you go or stick with your old faithfuls.

Worst Walking Tour Rip-Off

Walks where you have to backtrack. A good walking route gives you a new perspective all the time; you should never have to see the same thing twice.

When to Book

This varies by region, but seven to ten months prior to the trip usually means that you can reserve the best rooms and top guides.

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