10 Destinations Perfect for a Winter Vacation

Images: Shutterstock; Design: Samantha Shin/Thrillist
Images: Shutterstock; Design: Samantha Shin/Thrillist

Temperatures are dropping, jackets are emerging from storage — it’s The Most Wonderful Time Of The Year™ again. Unfortunately, the problem with winter isn’t so much that it’s cold, it’s that it’s long. By the time late January and February roll around, everyone is eager to be done with the chilly season. Winter vacationing is a crucial way to stave off cabin fever and get a change of scenery. When it comes to trips during the winter, there are two ways to go: seek shelter from the cold in the warmest places you can find, or embrace parts of the world that know the snow intimately. For our roundup of places to take a trip this year, we included both:

San Juan, Puerto Rico

This top vacation spot is a hot destination in winter thanks to unbeatable weather. Temperatures stay in the mid-70s even during the peak months of winter, and it’s only a short plane ride from the East Coast (3.5 hours from NYC, for example) with no passport needed. Old San Juan is full of beautiful, historic buildings, plus good food and friendly locals. Be sure to check out the pink sand beach of Isla Verde, home to plenty of resorts and hotels. San Juan is no stranger to tourists, so you’ll be able to partake in the usual beachy adventures, even in winter: paragliding, surfing, and boat rides are accessible just off the road from the airport. But for the authentic experience, be sure to take a trip into the city proper and check out the salsa clubs and bars. Having some Spanish will help, but you can also let your moves do the talking.

Quebec City

Quebec City is a true winter destination, with a charming small-village feel that was made for snowy days and long nights. Yes, you’ll need to bundle up, since average temperatures dip below freezing even during the day, but walking around the hilly sections of town will warm you up. Plus, those hills make for spectacular skiing and snowboarding at places just outside of town, like Le Massif. The Charlevoix region in general is beautiful, with rolling hills and fjords worth exploring. The city embraces the cold with its yearly winter carnival from (this year from February 4-13) — featuring snow sculptures, celebration of the area’s French heritage, and nighttime canoe races — and by building an ice hotel. You brought enough layers, right?


Lake Tahoe

Tahoe has taken on a certain rep among SF snow seekers for a reason. The area’s unique geology creates breathtaking panoramic views from the top of both ski slopes and hiking trails, but those looking to stay warm have options as well. The area is unusually sunny, even in winter, so you can get the goggle tan from the safety of your hot tub. The Nevada side of the lake keeps things lively, with casinos just across the state line and even more in Carson City. However, those looking for seclusion will find it: most of the surrounding area is made up of National Forest land, with plenty of opportunities for snowshoeing and backcountry skiing far from the crowds.

Costa Del Sol, Spain

Andalusia’s Costa Del Sol is a mix of Spanish, Mediterranean, and even British influences thanks to nearby Gibraltar. Málaga is the largest tourist destination and, but the entire coast is dotted with charming small towns like Estepona, Mijas, and Marbella. Each of these has historic Spanish architecture, mild Mediterranean weather, and numerous spas and resorts, thanks to the influx of visitors seeking a respite from the weather. Renting a car is recommended here, since you'll want to visit smaller towns and find tucked-away trails by the sea. This is also a must-visit spot for golfers, since the coast boasts the highest concentration of golf courses in Europe.


Myrtle Beach, South Carolina

Myrtle Beach is the hot spot on South Carolina’s Grand Strand, a great destination for both natural beauty and retro good vibes. The city’s Brookgreen Gardens hosts Night of a Thousand Candles, a Christmastime transformation that involves hand-lighting 3,000 candles among the oak groves. Without the summertime crowds, it’s easier than ever to take a peaceful stroll among the pristine shores of Huntington Beach State Park and visit Atalaya Castle tucked away behind the dunes. Of course, the city’s lively nightlife is still in force, with southern “shag dancing” happening at local spots like Fat Harold’s Beach Club.

Cartagena, Colombia

Getting below the equator is an easy solution to winter blues, since it just flips the seasons entirely. Although a bit further away than domestic spots (it's 5 hours from NYC flying direct, and many other cities will require a layover), Cartagena is a particularly great spot for the Endless Summer crowd, since it’s tucked in on Colombia’s Caribbean coastline. The Walled City is the historic portion of Cartagena, designated as a UNESCO Heritage Site due to the city’s history of fighting off pirates. Of course, beaches abound, but the city boasts museums for those looking for a more in-depth history or a look at the artistic traditions of Colombia.


New York City

New York, New York goes big in many ways, but the city really kicks off in December. City landmarks like Rockefeller Plaza transform completely, with a huge lit up tree, skating rink, and throngs of tourists. Shopping on Fifth Avenue is also a crowd draw, since flagships stores decorate elaborate window displays for visitors. If you’re looking for panoramic views of the Big Apple, skip the slog up the Brooklyn Bridge and try one of the city’s ferries instead, or walk along the Brooklyn waterfront. If a snowstorm rolls in, pop into one of the many bars with a fireplace to warm up. (Or, you could go in the complete opposite direction and join the brave souls taking a dip at Coney Island all winter long.)

Florida Keys

Florida exists as the pilgrimage site for many warm-weather seekers, and the Keys are the prime example of the place to hunker down during the cold months. US Route 1 connects the islands, allowing for easy access to different locales depending on your mood. Resorts line the shores too, so finding an affordable place to stay is possible, and fishing charters leave regularly from Key Largo, Islamorada, and many of the smaller island towns. If you really want to embrace the Keys vibe, check out the Hemingway Home & Museum and pet the famed author’s six-toed cats.

Aspen, Colorado

For those who spend winter on skis, Aspen needs to be on your bucket list. With four major mountains surrounding the city, you could explore the slopes here for weeks and never run the same route twice. (The total number of ski trails is over 300.) Of course, there’s no shortage of hotels and resorts to accommodate the skiers, with luxury favorites like the ski-in, ski-out Little Nell or the stunning St. Regis. After a long day flying down mountains, unwind in one of the local hot springs, like Glenwood Resort or the all-natural (and free!) Conundrum springs.

North Conway, New Hampshire

Unlike some of the other big names on this list, North Conway has a much more small-town vibe. Nevertheless, it holds up as a winter destination, thanks to the 700,000 acres of White Mountain National Forest surrounding the town, plus the backdrop of Mt. Washington, the tallest peak in the Northeast. Antique stores, cozy bed and breakfasts, and family-friendly resorts give the place an intimate feel, but the Mt. Washington Valley also happens to be a standout spot for ice climbing if you’re looking for something more adventurous. To really cap off the winter wonderland feel, book a sleigh ride at Farm By The River and traverse the fields the old-fashioned way (bundled up, of course).