The Best Winter Vacation Ideas, From Jackson Hole to the Azores
Once the cold settles in and the heavy coats come out of the closet, many of us find ourselves pulled in two completely different travel directions. On one side are the classic winter fantasies: Think snow-covered landscapes, ski slopes with cozy chalets, and impossibly charming Christmas markets. But once the holidays pass and the wind seems to cut a little sharper, an entirely different set of dreams comes into focus—and these are all about warm temperatures and sunshine that make you forget what month it is.
If you find yourself torn between snow and sand every winter, you’re not alone. Here, we’ve rounded up 25 of the best winter vacation ideas that suit every type of cold-weather wanderlust, from beloved Asian cities to quiet beach regions in Mexico. Consider this your excuse to make that winter travel wish list just a little bit longer this year.
Oneil Williams/UnsplashMedellín, Colombia
The temperatures in Medellín remain consistently perfect all year (it is called the City of Eternal Spring, after all), but you’ll encounter far less rainfall in the winter months. That gives you more daytime hours to explore this city that has emerged from its dark past to become a microcosm of Colombia’s progression into a bright and creative future. Named one of our best places to go in 2026, Medellín’s future—especially in the culinary world—is brighter than ever.
Micael Sáez/UnsplashNorthern Chilean Patagonia
While the appeal of Torres del Paine National Park is undeniable, our eyes are currently set a bit further afield. Northern Chilean Patagonia (another best place to go in 2026) is known as the Yosemite of South America, but unlike its Californian counterpart, it still flies slightly under the radar. Book a stay at Reñihué, a stunning fjord-side property, to view the region through a conservationist’s lens.
- Travel Wild/Getty
Sri Lanka
Sri Lanka is proof that the best things often come in small packages. Within its compact borders, you’ll find eight UNESCO World Heritage sites (including the striking rock fortress of Sigiriya), emerald-colored tea farms, beaches facing turquoise waters, and layers of history and culture in Colombo. The weather is usually best in winter (from December to mid-April), so book those tickets now.
Sandro Bisaro/GettyIceland
It’s a winter classic for a reason. Iceland may overflow with visitors most months of the year, but its winter activities and landscapes—from the peaks of Vatnajökull National Park to the ice-studded beaches of Jökulsárlón—are absolutely worth braving the crowds for.
Nik West/GettyRiviera Nayarit, Mexico
Mexico’s west coast is a reliable warm-weather winter getaway. Instead of staying in Puerto Vallarta, though, head north to the quieter, more upscale Riviera Nayarit. Aside from popular surf towns like Sayulita, the region is known for its natural beauty and excellent weather—expect pristine shorelines, a backdrop of the Sierra Madre mountains, and sunshine for 90% of the year.
Tatiana Kolesnikova/GettyBergen, Norway
With its colorful wooden buildings, fjord-front location, and scenic harbor, Bergen is like a snow globe setting in real life. The town looks beautiful in the summer, sure, but it’s during the winter months that you get to view the Northern Lights during their peak season. Because if you’re going to be freezing up in Scandinavia, you might as well get to cross an astronomical item off your bucket list.
Gary Yeowell/GettyDeath Valley National Park, California
Death Valley is nearly unvisitable in the summer, with temperatures often creeping above 120 degrees. Luckily, the national park’s moonlike topography and rocky features are beautiful all year—and with winter temps hovering in the 60s and 70s, you can actually enjoy them without completely melting. Be sure to set your alarm to catch the sunrise from Zabriskie Point.
Ihor_Tailwind/GettyPrague
If you thought Prague was beautiful in the summer, just wait until you see it in winter: The city’s Gothic architecture provides the perfect backdrop for savoring sugary pastries and roasted ham, warming up on mulled wine, and indulging in some major holiday shopping. Prague’s main Christmas markets take place in the Old Town and Wenceslas Square, which are conveniently just five minutes apart on foot. Aside from the aforementioned food and beverages, the markets are filled with traditional Czech goods and ornaments, and marked by a frenzy of holiday carols and lights.
Peter Adams/GettyOkavango Delta, Botswana
Botswana isn’t simply somewhere to escape the cold—it’s a bona fide paradise. Surround yourself with bathing zebras and grazing giraffes as you traverse the river via mokoro canoe, and don’t miss out on the unreal birdwatching. You can stay in an array of buzzy safari lodges that, while still extremely comfortable, eschew over-the-top amenities in favor of a true wildlife lover’s experience.
Getty ImagesMontreal, Canada
Even when the winter months turn the city white, Montrealers don their matryoshka doll layers and take the city by storm. You’ll see them both warming up inside with kittens at North America’s first cat café and headbanging the night away at Igloofest, the coldest music festival in the world. Even as snowfall drops by increments of feet, you can’t help but fall in love with the city’s outgoing spirit—and warm culinary scene.
Simon Bradfield/GettyZakynthos, Greece
All Greek islands seem to be framed by that killer shade of emerald blue, but there’s something about the white sand beaches and brilliant waters at Navagio Bay in Zakynthos that will make your heart skip a beat. Its secluded location (it’s sheltered on either side by soaring cliffs) keeps its aquamarine waters so perfect and pure—basically the exact opposite of winter grays.
Rolf Blicher Godfrey/UnsplashCopenhagen
When you visit the birthplace of hygge (the Danish concept of “coziness”), you better believe your winter vacation is going to be aces. That feeling can be found throughout Copenhagen, from pastry shops to inviting hotels.
Chaodao Zhang/GettyBoracay, Philippines
Consistently voted one of the best islands in the world in our Readers’ Choice Awards, Boracay is a favorite of locals and tourists alike. The idyllic white sand beaches were so popular with visitors that, at one point, the authorities had to prohibit tourism for a while to let the land and community rehabilitate. But now it’s back in business, ready to welcome those looking to relax and unwind, or party the night away—or both.
Xavier Balderas Cejudo/UnsplashGreenland
Icy and mysterious, Greenland is one of the most naturally beautiful places on earth. The world’s biggest non-continental island is so much more than glaciers (but yes, the glaciers are spectacular)—think magnificent fjords, colorful villages, and fields of sheep. Throw in some northern lights appearances, and you have yourself one of the best winter vacation ideas.
Joel Rohland/UnsplashCanary Islands, Spain
It’s not quite hot enough to swim off the white sand beaches of Spain’s Canary Islands in the winter, but to make up for it, there are fewer crowds, ever-impressive views, and off-season prices on this cluster of volcanic isles. For what it’s worth, the island of Gran Canaria, just off northwestern Africa, is said to have the best climate in the world.
OhKobayashi/GettyHokkaido, Japan
The Japanese island of Hokkaido is blessed with myriad geological beauties (think volcanoes, national parks, and lakes), most of which are even more stunning in winter. For example, the ethereal Shirogane Blue Pond wears ice beautifully, with its towering trees and azure waters coated in glimmering frost. Looking to ski? The slopes of Niseko are among the finest in the world.
John Harper/GettySingapore
There’s no better place to escape the winter cold than right on the equator, which is pretty much exactly where Singapore sits. Inclement weather won’t stop you from visiting the city-state’s many hawker centers, museums, boutiques, and night markets. This city in a garden is a perfect way to relieve your eyes of the winter grays and give them some verdant life.
Anshar73/GettyZermatt, Switzerland
Zermatt, surrounded by some of the Alps’ tallest peaks, has 223 miles of runs in four huge ski areas—some at an altitude of over 10,000 feet, meaning snow here lingers for a very long season. This enchanting Alpine village lies at the foot of the Matterhorn, Switzerland’s most famous mountain, and has plenty of modern touches, like its state-of-the-art lift system and swanky après-ski diversions.
Ze Paulo Gasparotto/UnsplashFernando de Noronha, Brazil
If the famous beaches of Rio are getting too crowded for you, head 220 miles off Brazil’s northeastern coast to the breathtaking archipelago of Fernando de Noronha. Here you can snorkel in crystal-clear waters, trek lush trails, and watch the moon rise over the ocean.
JellisV/GettyFinnish Lapland
Imagine the most idyllic winter scene you can dream up, and Finnish Lapland will absolutely deliver. There aren’t many places where you can visit Santa Claus, take a reindeer sleigh ride, or sleep under the Northern Lights in a bubble sled—but Lapland lets you do all three.
Claudio Fonte/UnsplashCape Town
From December to March, South Africa’s safari circuit takes a back seat to Africa’s most cosmopolitan city, thanks to prime weather conditions. During the Southern Hemisphere’s summer, Cape Town’s restaurant, hotel, and nightlife scenes are at their best. Plus, it’s the growing season in South Africa’s winelands, from Stellenbosch to Franschhoek to Swartland, all of which are just a short road trip away.
Deberarr/GettyNew York City
Not many cities can compare to New York City during the holidays. The classics continue to shine bright: the lighting of the Christmas tree in Rockefeller Center, the Christmas Spectacular Starring the Radio City Rockettes, ice skating in Central Park, and The Nutcracker at Lincoln Center. Once you’ve covered those, head out of the city to some of the best skiing in the northeast.
Fred Froese/GettyChiang Mai, Thailand
Chiang Mai in Thailand is surrounded by misty mountains, golden temples, and verdant rice terraces—all with a climate that rarely dips below 60 degrees. During the city’s Flower Festival, held annually on the first weekend of February, every street in the old city is covered in flowers and plants for three days.
Courtesy Caldera HouseJackson Hole, Wyoming
This Teton-ringed valley is a true winter wonderland. Of course, it helps if you want to spend most of your time skiing—Jackson Hole is known for its 3,000 acres of both accessible backcountry terrain and challenging vertical slopes. But even if you don’t want to hit the powder, you can still indulge in après-ski diversions in both Teton Village and the town of Jackson. And let’s face it: Any excuse to cozy up in Caldera House is a good one.
aragami123345/GettyThe Azores
While it may seem counterintuitive to fly to an island for the cool weather, it’s exactly that brisk and fresh feeling that’ll enchant you in the Azores, an archipelago in the middle of the North Atlantic. All that lush greenery and pleasant chill will let you discover a new kind of sweater weather, and it’s just a five-hour flight from the US.
This gallery has been updated with new information since its original publish date.
