Where to Travel this Fall and Winter to Escape the Cold

Everyone has that moment when it hits them that colder weather is on its way. For some, it’s noticing the shedding trees, or sleepily waking up to the first snowfall, and frantically rubbing your eyes in the hope that it’s not real. Perhaps it’s the day you add an extra layer to your ensemble, and switch your iced coffee order to a cappuccino.

Whichever way it dawns upon you, realizing the summer is over has a way of making you want to curl up and hibernate. Or rather, it reminds you there’s no better time to join forces with friends and family, escape the cold and explore somewhere new. We’re part of the latter camp.

Enjoy fewer crowds, warmer temperatures, and throwing the daunting idea of winter on its head with our picks of the best places to travel in fall and winter to escape the cold.



While everyone else elbows for space beneath Japan’s cherry blossoms in spring (though we admit, it’s quite the breathtaking sight), you’ll be breezily basking in the fiery hues of its autumn foliage. Pair the striking landscape with piping hot onsens to keep the cool evening air at bay, and you’ve landed on one of the prime times to go to Japan. 

Best Places to Travel Fall Winter

Why go to Japan in 2020-2021: The 2020 Olympics will heighten the atmosphere in Japan, helping to build upon its inbound tourism (like more flights between North America and Tokyo). We’ve also just returned from doing extensive research for a new trip on the subtropical Kyushu Island that we’ll be launching this year. Want to be among the first to hear about it? Send us a note.

One of our favourite B&R moments in Japan: Cycling around Noto Island and keeping our eyes peeled for dolphins before lunch in a farm-town restaurant that serves the tastiest tempura and handmade soba noodles on the peninsula.


Skip the scorching summer heat and head to Morocco in October, just before the High Atlas Peaks receive their first dusting of snow. In the palm grove of Skoura (where we visit on our Morocco Active Expedition), you’ll be just in time for date harvesting season and later in the journey in Marrakech, revel in the quietude of its exceptional gardens, following in the footsteps of one of the country’s most revered guides.

Best Places to Travel Fall Winter

Why go to Morocco in 2020-2021:  In 2019, Marrakech was awarded the title of African Capital of Culture 2020, attesting to the city’s rich history (it’s the home of two UNESCO World Heritage sites) and burgeoning art scene.

One of our favourite B&R moments in Morocco: Crossing the desert dunes on camelback to a private Berber camp for a feast beneath the starry desert sky. 



The landscape of this sliver of land changes swiftly between its northern and southern corners, swinging from desert plains to glacial fjords to temperate rainforest. No matter which terrain you choose to explore, November is an ideal time to visit: Spring is in full bloom in the southern Patagonia region, while the drier and warmer temperatures of the north offer an opportune time to pedal amid the fields of vineyards and Andes mountains.

Best Places to Travel Fall Winter

Why go to Chile in 2020-2021: The Tompkins Conservation made the largest private land donation in history last year and created two new National Parks in Chile, totalling an impressive 41 across the country. Plus, increased flight connections between Santiago to Puerto Natales will make it easier to access Torres del Paine National Park in Patagonia. 

One of our favourite B&R moments in Chile: Riding from the coast into the countryside in the Colchagua Valley on our Chile Wine Country Biking trip to a sumptuous picnic spread, followed by a cooking class with one of the country’s most celebrated chefs.

New Zealand

November is shoulder season in New Zealand, meaning summer and an influx of tourists are just around the corner. Come early to enjoy the country all to yourself (almost—you’ll be competing for space with some 30-odd million sheep) and take your pick of world-class hiking trails with wineries to match. Turn to our resident Kiwi and trip planner, Rob Grieve, to craft an adventure of a lifetime.

Best Places to Travel Fall Winter

Why go to New Zealand in 2020-2021:  Travel to New Zealand from North America will be made easier with the first direct, non-stop flight between Los Angeles and Christchurch coming in October 2020.

One of our favourite B&R moments in New Zealand: Venturing across Lake Te Anau to Milford Track with an expert in Kiwi flora and fauna and meander along the Clinton River. In a word: stunning.



Gather the family for a trip to Argentina and spend the holiday season pedalling past rust-coloured mountains, glittering salt pans, and Colonial towns. Rather than gathering around a turkey (which we all know is greatly overrated), you’ll be feasting instead on the country’s famous tender cuts of beef washed down with a glass of inky Malbec.

Best Places to Travel Fall Winter

Why go to Argentina in 2020-2021:  One of the year’s most exciting astronomical events will take place on December 14, 2020, when a total solar eclipse will pass over the Patagonian Steppe of Argentina.

One of our favourite B&R moments in Argentina: Riding through a cloud forest to the polychromatic Humahuaca Canyon in Northern Argentina, and taking a break to lunch at a family-run sugar plantation.


The sprawling Angkor Wat temple complex is worth a visit any time of year, but in December, when temperatures hang around a pleasant 30°C (86°F), you’ll soak up its beauty without soaking in sweat. Your trusty e-bike lets you cruise around without exerting too much effort, keeping you cool and allowing you to reach the further (and lesser-visited) corners of the park. After, return to your resort for a moment of respite by the infinity pool.

Best Places to Travel Fall Winter

Why go to Cambodia in 2020-2021: The Kingdom has been making efforts to clean up its coastline and open up more beachside options for its visitors, helping to ease over-tourism at the temples that have long been the country’s biggest draw. 

One of our favourite B&R moments in Cambodia: Zipping alongside the floating villages on Ton le Sap Lake on our e-bikes to arrive at the wild jungle temple of Ta Prohm, just in time to catch the sunset.



Nothing stops the drudge of January dead in its tracks like the beachy vibes of Uruguay. We’re not sure how such a small country packs such a huge punch, but it has it all: an emergent wine scene, an innovative arts community, and dreamy seaside resorts. Seeming to naturally embrace the ethos of slow travel, head to Uruguay to kick back after the holiday bustle.

Best Places to Travel Fall Winter

Why go to Uruguay in 2020-2021: In Punta del Este, a new Museum of Latin American Art will open in 2021, adding yet another reason to visit one of our favourite beach towns. We also love how the country is making strides in sustainability and set forth a national plan to improve the country culturally, environmentally and economically through its tourism offerings. 

One of our favourite B&R moments in Uruguay: Rolling through the ‘Tuscany of Uruguay’, pausing to sample olive oil with a boutique producer and tasting a local Tannat Reserva on our Uruguay Biking trip.

Sri Lanka

With influences drawing from Portuguese, Dutch and British cultures, a visit to Sri Lanka can feel like a trip around the globe. Adding to this diversity is an array of ever-changing scenery and sites—hilly tea plantations to Azure coastline, Buddhist temples to ancient fortresses—three official languages (Sinhalese, Tamil and English) and incredible wildlife (elephants and leopards and deer… oh my.) This isn’t the Land of Oz, but it certainly is magical.

Best Places to Travel Fall Winter

Why go to Sri Lanka in 2020-2021: After a difficult 2019, Sri Lanka is making a comeback and ready to welcome travellers with open arms. It’s on many lists as a hot travel destination for 2020, but we’ve been heading here for years and know what you should discover, both old and new. 

One of our favourite B&R moments in Sri Lanka: Pedalling along an old king’s route through market towns brimming with exotic vegetables, which we’ll get to sample during a meal in a Sri Lankan home (we even help prepare some of the dishes!).



Vietnam has made the cut as one of our favourite places to travel in winter for the past twenty years, and it doesn’t look like it will lose its ranking any time soon. Our friendships run deep here, like Duc, who invites us to an intimate meal at his top-rated restaurant in Hoi An, and our longtime local guide, Tam Dinh, who’s been regaling travellers with stories of his home country for more than a decade.

Best Places to Travel Fall Winter

Why go to Vietnam in 2020-2021: Condé Nast acknowledges our Vietnam Trip Designer, Nathan Lane, as a Top Travel Specialist for Vietnam by Condé Nast. We already knew he was ahead of his game. But now that it’s been made official by one of the most discerning travel publications—don’t miss the chance to have him plan your journey. 

One of our favourite B&R moments in Vietnam: Sharing a home-cooked meal in the backyard of a relative of the Nguyen Dynasty (who also just so happens to be one of our close friends) on Vietnam and Cambodia Biking.


Swap the drab shades of February for technicolour temples, neon nighttime food markets and vibrant florals (like those at the Chiang Mai Flower Festival in February) in Thailand. Temperatures will be cool and dry, perfect for riverside rides past rice paddies. You may, however, break a sweat eating some spine-tingling spicy dishes. But nothing a dip in the dreamy pool of The Peninsula Bangkok can’t fix.

Best Places to Travel Fall Winter

Why go to Thailand in 2020-2021: Thailand has had a bad rap in the past of attracting hordes of tourists. However, its government is making moves to disperse travellers to other corners of the country. With B&R, your trip will be in the hands of Karen MacRae, who lived in Thailand for many years and can show you a side of it that others often miss.

One of our favourite B&R moments in Thailand: Countryside riding interspersed with market stops to sample the local food (is there any better way to do it?) on our Bangkok to Chiang Mai trip.

Have another destination in mind? Our experts love to talk about travel to anywhere, anytime. Contact us here.

The Slow Road



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