Life

Travel Writers And Influencers Tell Us Their Favorite Destinations For Winter

As winter sets in across the northern hemisphere (and summer in the southern), travel is on everyone’s mind. The idea of escaping the biting cold to someplace warm is an intoxicating one. Or maybe you’re someone who goes all-in on the season and finds that perfect cabin on the side of the mountain to watch the snow pile up. That’s what is sort of great about winter, you can get the best of both worlds without having to travel too far from mainland North America.

We decided to ask some of our favorite travelers — raconteurs and vagabonds who are on the road right now — where they love to go in the winter. There’s a great array of answers below, ranging from sweltering tropics to those snowy mountainsides. Hopefully, their expert advice will give you the motivation to hit the open road this winter too.

STACEY LEASCA (sleasca) — DARBY, MONTANA

Darby is a super small town with about 700 residents located in the southwestern part of the state. What it lacks in population it more than makes up for in adventure. In Darby, visitors can ski, go on winter cross-country horseback rides, snowshoeing, snowmobiling, and so much more.

Perhaps the most exhilarating (and adorable) things visitors can do in Darby is head out for a dog sled ride. In Darby, guests can ride out with Evermore Adventures, a dogsledding operation helmed by two of the leading women in dogsledding. The rides last for several hours and include a pitstop at the top of a mountain with a cup of hot chocolate.

If you’re nice, they may even let you hold a puppy… or two… or three!

MATT PAYNE (mattpaynetravelphotography) — BANFF NATIONAL PARK, CANADA

Banff is an epic backdrop for just about any winter activity. While I love adrenaline as much as the next guy, my favorite experience during my stay at the Banff Springs Fairmont was far more passive: Ice fishing.

The journey began with a snowy trek through the forest to the shores of the very frozen Spray Lakes. A couple of snow kiters ripped around us as we made our way to a tiny shed where I’d spend the next few hours sitting on a box in a heated shed on a frozen lake sipping cider and noshing on locally sourced sausage on a fresh baguette.

Our guides from Wapiti Sports & Outfitters drilled for holes (one in each corner of the shed) and dropped baited lines in the water. Then we took a seat and waited. The shed was just warm enough to be comfortable and sips of whiskey from a smuggled flask warmed me a bit more. Periodically, I’d step outside and take in the towering sun-soaked snowy mountains that surrounded the lake. There was something primal about the silence as the piercing cold wind ripped across the lake, kicking up the snow as it blew. Eventually, the fishing poles snapped tight. Hooks set. And, within a few intense minutes, we’d caught a dozen trout.

We took them to the cook shed, where our guides cleaned and cooked the fish on site. It was quite a lunch. The cleanest fish I’ve ever eaten in one of the most beautiful spots in the world.

CIARA JOHNSON (hey_ciara) — ASPEN, CO

I went to Aspen for the first time earlier this year and it was my favorite winter travel experience! I got to dive into the ski town’s history at the Aspen Historical Society. I enjoyed taking snowboarding lessons at Buttermilk Mountain, which give me a chance to step outside of my comfort zone.

I was able to cut costs by staying at the Limelight Hotel which offered a complimentary shuttle, morning slope runs, free breakfast, and a happy hour! Free activities like the Aspen Art Museum and the winter wonderland that is the Aspen Center for Environmental Studies also allowed me to stay on budget.

I really enjoyed the Apres Ski culture after a long day on the slopes because who can complain about half price drinks surrounded by a fireplace? You can’t. I’d certainly return during the summertime to see a different side of Aspen. After all, the Food & Wine Classic is calling my name.

ZACHARY WEISS (zacharyweiss) — SAINT MORITZ, SWITZERLAND

It’s not easy to get to St. Moritz. Yet every time I find myself there, it’s always worth the trek. It begins with a four-hour train ride from Zürich. The train winds along the snow-covered Alps until you happen upon a small town with a year-round population of just over 5,000 residents. That number swells during the winter season. Plenty of skiers come out in droves. But, more often, the crowd is made up of holiday travelers looking to enjoy everything St. Moritz has to offer.

It’s all centered around Lake St. Moritz, which freezes over in the winter to create a sort of stadium for activities. Visitors can spectate a snow polo match or even try their hand at Skijoring — skiing while being pulled by a horse. The Cresta Run is nearby too, an ice track founded in 1884. You can partake if you’re crazy enough to zip down the course, head first on a toboggan, at speeds of up to 85 MPH. Legendary playboys like Gianni Agnelli and Gunter Sachs were among the club’s revered membership.

But for me, the best part is the hotels that feel plucked right out of The Grand Budapest Hotel, with the loyal staff to match. My go-to is the Kulm Hotel. The Kulm offers a perfect mix of old-world charm and modern amenities, like an outdoor heated pool overlooking the mountains.

SOHEILA HAKIMI (isthatsoh) — ASPEN, COLORADO

Being from Canada, where winter makes up a third of the year, I typically yearn for escapes to warmer destinations. But, last year, I went to Aspen for a quick four-day getaway and found myself embracing the snow again!

As a teenager, I loved winter and welcomed weekends with friends snowboarding at ski resorts near my home but somewhere along the way life pulled me away. By the time my trip to Aspen rolled around it had been over a decade since I had last been on a snowboard. I vividly remember sitting ankle deep in fresh powder, 12,000 feet above sea-level with the cold winter air in my nostrils and I. was. nervous! Thankfully, it didn’t take long for muscle memory to kick in and, before I knew it, I was gliding down the hills as gracefully as I used to.

Although the skiing alone was incredible, what made this winter escape feel so different was a whole other element I could take advantage of, APRES! As much as I had fun skiing, I also had a whole lot of fun après skiing and Aspen’s après scene sets the bar high!

KARL WATSON (karlwatsondocs) — INDIA

I much prefer the heat to the cold. I work as a freelance video editor between my travels, and there’s never any work on in January. So as soon as Christmas is done, I head off on an adventure for a few weeks. It’s amazing because it means I never get the January blues. This year I’m off to Vietnam, exploring the whole country from south to north.

One trip I did back in 2016, though, was six weeks traveling around India. Winter is the perfect time to go because the cities in the north aren’t scorching hot. They’re already busy and crazy enough as it is. You don’t want to add in boiling hot temperatures to that mix.

My trip finished right at the very south of India, a little beach town called Varkala. Sitting on the beach enjoying a beer in February, nothing beats it! Good spot for a bit of paragliding as well.

MELANIE SUTRATHADA (melaniesutra) — ICELAND

There is no destination more magical to me than Iceland in the winter. Think stunning frozen waterfalls, crystal blue ice caves, and beautiful Icelandic horses with their thick winter coats. Add in the dancing northern lights and steamy natural hot springs, and Iceland is essentially the winter wonderland that you’d picture in a Disney movie.

The days are shorter during this time of the year with only four or five hours of light each day, leaving you with dreamy sunrises and sunsets that seem to last for hours. Let’s just say that this season is the perfect time to book a flight to Iceland!

JUSTIN WALTER (atwjustin) — SUN VALLEY, IDAHO

Living in California, it’s been my tradition to do at least one ski weekend every winter which has included hot spots like Mammoth Lakes, Tahoe, and Big Bear. Last year, however, I discovered a hidden gem a short flight from LAX (two hours and change). Say hello to Sun Valley, Idaho!

As a winter destination, Sun Valley offers a storybook wonderland where instead of feeling like a tourist, guests live like locals among warm and welcoming residents. During my visit in the height of a winter weekend, Sun Valley was the least touristy ski resort town I’ve ever been to. In California, I’m used to long lines and crowded slopes, but here I felt as if I had “Baldy” (aka Bald Mountain) all to myself! Powder conditions were perfect and my time in Sun Valley transported me into an idyllic real-life snow globe.

Beyond the slopes, the region is made up of a cluster of small towns full of kitschy yet cute restaurants (check out Pioneer Saloon) and local breweries (try Sawtooth) that hit the spot for all your après ski needs.

Did you know Idaho had such an untapped and pristine winter escape? You do now. Thank me after your first run down the slopes…

CHARLOTTE & NATALIE (ourtasteforlife) — NEPAL

After spending some time in Nepal last year, we’d have to say this is our all-time favorite Winter destination. Although temperatures are often bitterly cold, it’s also when the country sees its clearest conditions, allowing unobstructed views of the snowcapped Himalayan mountains.

For sensational views and a magical winter vibe, we recommend heading to the sleepy town of Pokhara. It’s the kind of place that has you forgetting that anywhere else in the world exists. You’ll be content immersing in the tranquillity such conditions provide.

The center point of the town is the majestic Fewa Lake which boasts a jaw-dropping backdrop of the Annapurna mountain range. I’d freely say it’s one of the most beautiful places on earth. Or if you’re up to the challenge, you could even take on one of the various trekking routes such as Annapurna Circuit or Annapurna Base Camp.

FORREST GALANTE (forrest.galante) — MICRONESIA

Well, I’m not a cold-weather person. So for me, a perfect winter is spent exploring remote coral atolls of Micronesia looking for previously unidentified species of endemic reef fish, studying stinger-less jellyfish, making bonfires on uninhabited islands to cook a freshly speared snapper, and climbing trees to pick coconuts.

In other words, if I have to even have a shirt on, it’s too cold to call it a vacay!

TERESA CESARIO (teresacesario) — COSTA RICA

When you live in Miami Beach, it’s hard to imagine a more perfect place to spend your winter. But there are times even flamingos get bit with the travel bug. When this happens, I find myself wanting to travel with intention.

My sister and I began planning a trip to Costa Rica this past summer after learning only one in 1,000 leatherback turtles make it to adulthood. I’m currently writing this article from Costa Rica where I gathered 15 hospitality veterans who wanted to donate their time as well as dine and drink around the city of Nosara. In this beautiful city, we’ve found our home away from home at the Bodhi Tree Yoga Resort. The resort provides us with daily yoga classes, fresh juices, and a surprisingly great bartender named Vida.

The restaurant and bar scene around Nosara is growing and includes a members-only lounge called ”Black Sheep.” This Irish bar in Costa Rica is just offbeat enough to make a Miamian feel at home.

Tomorrow under the crescent moon we’ll watch baby turtles hatch and protect them as they make their way into the ocean. This only happens in the winter months. It’s an amazing way to give back while being gluttonous. Pura Vida!

ERIN ROSE BELAIR (roseblacque) — IDAHO

I rarely seek out winter destinations. I love a nice cabin and a good book, but for me, winter usually means hunkering down and getting some writing done. Which is probably why my pick for a winter destination is Idaho.

It feels like home and yet offers up all the magic of winter I miss in California. It has the ability to wrap you up and make you forget there’s anywhere else you’d rather be. It’s slow and thoughtful, quiet and cold, an old book you once read, the friend that you miss. It feels nostalgic even if it’s your first visit.

Plus, there is no better feeling than soaking in a natural hot spring while the snow falls all around you. And, there’s great skiing in Sun Valley, incredible bars in Boise where one can sip a Manhattan and warm up, and gorgeous snowy drives up to the Sawtooth Mountain’s that’ll take your breath away.

CHARLES THORP (charlesthorp) — SAN JUAN, PUERTO RICO

Puerto Rico is a worthy destination no matter where you live in the world, but for those of us who live on the East Coast of the United States, it’s a Caribbean paradise reachable in under four hours. The island is a perfect escape from the frozen faces and the frostbitten hands that come with the daily commute. I enjoy my ski weekends, but eventually, you reach your breaking point.

The beauty of the San Juan area is that it has everything that you could possibly want for your warm-weather getaway and more. I have gotten good at taking advantage of that by first staying at an AirBnB outside of the city proper to enjoy the quieter life and to be closer to El Yunque rainforest which provides some of the best hiking and horseback riding I’ve ever experienced. The beaches outside of the city are also quieter, and so you can spend hours just listening to the waves crash without being bothered.

Once there’s been the proper fill of adventure, I make the move for a few nights in Old San Juan. Last time I was there I stayed at El Convento, a charming little hotel built in the 17th-century. There you can walk around and explore the history of the island, hitting landmarks like the beautifully decrepit Castillo San Felipe del Morro. The rest of the day is spent eating everything in sight, drinking at great cocktail bars, and dancing until the legs burn.

WRITER’S PICK: ZACH JOHNSTON (ztp_johnston) — SICILY

Ah, Sicilia.

I live in Berlin where it gets so, so cold. So when I can escape my desk in winter, I head south to Italy.

Southern Italy is a wholly different world from the rest of the country and that’s extra true of Sicily. I tend to make basecamp in Palermo, a bustling city that spans millennia — holding endless stories of lost cultures, bitter wars, and fascinating people. The place is a wild mix of amazing aromas wafting from street food carts on (seemingly) every corner, bakeries making every type of pizza you can image (don’t sleep on the hot dog and fries pizza, seriously), and outdoor food markets slinging everything from the land and sea.

The seaside city offers you a chance to sail or fish if you’re so inclined. The city’s train station is a great way to take day trips all over the country (though the road system is pretty top-notch too). A trip to Agrigento on the southern coast is the home to one of the largest and best-preserved ancient Greek cities on the Mediterranean is a must. To the east, Etna still rumbles and spits fire every now and then. Oh, and the beaches — the island is a wonderland for beach bums looking to just chill, take in the sun and sea with a Negroni in hand, and let the day slip away.

There’s also a wild and dangerous feel to Sicily, Palermo especially. Street food markets are built on rubble from World War II. The mafia is 100 percent a part of the city’s economy and openly operating on the streets. There’s an edge to Palermo and Sicily that makes you feel alive. Add in an amazing food scene, awe-inspiring villages on mountaintops, idyllic beaches with crystal clear azure water, and all the wine and you have a spot that’ll give you a hard reset during the harshest of winters.

And, yes, you will hear The Godfather wedding theme about 20 times a day. It rings out from lone street trumpeters, tourist shops, train station platforms, corner stores, and people’s ringtones.

EDITOR’S PICK: STEVE BRAMUCCI (stevebram) — NORTH SHORE, OAHU

Steve Bramucci

That pic was taken two days ago, on Oahu’s North Shore, so obviously I’m biased. The man with me is beloved surfer and lifeguard Rocky Canon, so I’m also obviously lucky as hell. To spend time on the “Seven Mile Miracle” with a guy like Rocky, who knows every break better than I know the contours of my keyboard, is a huge advantage for anyone trying to catch rides on the North Shore.

This is surfing’s Mecca. Yes, I know that term has fallen out of favor as a metaphor over the past few years but I’m using it correctly here. It’s a place where the kinetic and spiritual sides of the sport collide to create a hallowed ground that every adherent to the culture should visit at least once. Hyperbole? If anything, I’m understanding things.

Will it be boring if you don’t surf? Not a chance. Rather than chasing waves (always defer to locals; always defer to pros) you can spend your days watching them. The Vans Triple Crown of Surfing takes place on the North Shore, with three pro tour events stretching across November and December. In December, the Billabong Pipe Masters is held at the world’s most famous wave, Banzai Pipeline. If the waves are firing, and they will be for at least part of the contest, it is an absolute marvel to behold.

There’s only one real “resort” on the North Shore and it has gone to great lengths to fit in with the local “keep the country country” mentality. Book in at Turtle Bay — probably the best break along the Seven Mile Miracle for intermediate surfers (beginners should stick to Honolulu) — and lounge in the pool, do karaoke at the Surfer Bar, retrace Jason Segel’s footsteps (this is where virtually every second of Forgetting Sarah Marshall was filmed), and check out one of the daily spa happy hours.

This is island living at it’s best: warm, slow-paced, filled with beautiful people, and tons of activities for you to think about doing and then decide to skip in favor of eating a shave ice while watching Kelly Slater and John John Florence rip waves.

(Extra Bonus Tip: Model-turned-shark advocate Ocean Ramsey leads tours to dive with sharks in the waters just offshore from Haleiwa. This is the sort of guided and safe excursion that feels like a glimpse at the future of animal-based tourism — with money from every tour going to protect sharks and preserve their habitats. It’s also a ton of fun.)

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