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Fun Places to Vacation During Winter Holidays

By Olivia Harlow

At the first sight of snow or the first feel of a cool winter wind, winter vacation beckons. Powdery mountains call to the spirit of snow sports enthusiasts, who instantly pack up ski bags, splurge on season lift tickets, and hit the slopes.

For others, it’s distant, sun-drenched tropical beaches that summon the soul. Whatever your interests, we’ve got you covered with some incredible winter destinations.


For the Ice Queens/Kings:




Crested Butte is one of those rare places that is magical year-round, but it especially attracts ski and snowboard bums during winter months each year. This charmingly adorable town is set in the Rocky Mountains, offering outstanding downhill skiing and mountain biking. The state’s West Elk Loop Scenic and Historic Byway offers lovely views of wilderness areas such as the Kebler Pass mountains. After a day swooning over glittery white mountaintops, you’ll want to wander the town’s local shops and restaurants on Elk Avenue. Be sure to stop in Bonez for margaritas and tacos at night, and Izzy’s for a lush breakfast the following morning.




Just north of Vancouver, Whistler Blackcomb is one of the largest ski resorts in North America and has consistently been rated a “best of” destination around the globe. In addition to traditional skiing and snowboarding, the area offers snowshoeing, tobogganing, and ski jumping at Olympic Park–the venue used in the 2010 Vancouver Winter Olympics. The town’s urban center is a chalet-style, pedestrian village at the base of the mountains, offering gorgeous 360 views, incredible dining options, and cute boutiques, and relaxing spas.




Located on Japan’s Hokaaido Island near the dormant volcano of Mt. Yotei, Nikseko has been officially noted Japan’s #1 snow resort and one of the best skiing destinations in the world. Home to the slopes of Mt. Niseko-Annupuri, snow sports enthusiasts flock to its dramatic powder bowls and tree runs, covered in an average of 15 meters of pow each season. In addition to traditional winter sports, visitors can try out heli skiing, snowmobiling, cat skiing, and snowshoeing. And after a long day of shredding, there’s nothing better than an evening at the spa. Be sure to stop in to any of the area’s countless hot spring resorts, or “onsen.” (For tips on respecting the tradition, read here.) If you plan your visit in February, be sure to check out the Sapporo Ice Festival—a seven-day event with ice sculptures, snow slides, ice skating, and various other exciting activities, which brings in approximately two million visitors from around the world each year. At night, explore the local Kutchan Town, a fabulous place to experience authentic Japanese cuisine and nightlife.




This small alpine town is a great place to witness Austria’s raw beauty and experience its thrilling downhill skiing. Skiing, particularly, is the area’s favorite sport and outdoor activity. The legendary Kitzbühel  Streif is a highly regarded downhill ski race track, bringing some of the world’s best skiers for a challenge. If you don’t want to participate, be sure to at least observe! Snow shoeing is another great way to hike some of the mountains during winter months. In addition to outdoor sports, upscale shops and cafes line the streets of its medieval town center. Impressive art-focused museums also intrigue visitors far and wide–specifically Museum Kitzbühel, which offers a rooftop terrace with unimaginable views.




The small town of Jackson is located in Wyoming’s Jackson Hole Valley—an iconic ski area, home to well-known runs including Jackson Hole Mountain Resort, Grand Targhee Resort, and Snow King Mountain Resort. That said, there’s so much more to the quaint town aside from its top-notch pow. The National Elk Refuge—which was established in 1912 to help preserve the local elk population—is a serene sanctuary for the migrating creatures from fall until spring. The National Museum of Wildlife Art features artwork by Andy Warhol and Georgia O’Keefe, and just north are the famous Teton mountains and Yosemite National Park. After a day out and about exploring the arts and playing in snow, you’ll want to warm up by the fire with a glass of whiskey and a meaty platter from Million Dollar Cowboy Steakhouse. To no surprise, Jackson’s art, culture, amazing food, world-class skiing, and intriguing nearby getaways, make this vacation so much more than a ski trip. And if you can’t get enough of this magical place (trust us, chances are you won’t want to leave), here’s a list of local events and festivities happening year round.


For the Beach Babes:




This Hawaiian island is nicknamed “Garden Isle,” due to its tropical rainforest coverage. Dramatic cliffs and pinnacles line the Na Pali Coast, and the stunning Waimea Canyon follows the state’s iconic Sleeping Giant mountain ridge. Of course, the island has fabulous beaches, but it’s impossible to visit Kauai and not explore its mountains. (For hiking ideas, check here.)




This small South Pacific island is just northwest of Tahiti, surrounded by crystal clear ocean. Known as one of the most romantic places in the world, Bora Bora is home to hibiscus flowers, palm trees, stunning beaches, rising mountains, and luxury bungalows. At first look, its vibrant coral reefs, white sands, and turquoise waters are seemingly unreal. A 727-meter dormant volcano rests in the island’s center, which gives life to two peaks: Mt. Pahia and Mt. Otemanu. And the beaches’ scuba diving brings you face-to-face with manta rays, colorful fish, and underwater gardens.




Whether you’re exploring the Spanish architecture and bustling nightlife of San Jose, climbing the epic Talamanca Mountains near the Central Valley, ziplining through the rainforests of Montezuma, or laying on the beach at Playa Hermosa–Costa Rica is an unbeatable sunshine-drenched getaway during the cooler months. Be sure to visit Manuel Anotnio—the country’s most popular beach, studded with palm trees and lined with jungle. It’s the perfect place to add thrilling adventure to a typical relaxing beach vacation.




Propped along the Caribbean coastline of Mexico’s famed Yucatan Peninsula, Tulum is a South American icon, known mainly for its serene beaches and ancient Mayan history. In addition to lounging on white sands and diving in pools of pure blue sea, be sure to check out the Parque Nacional Tulum—an interesting park with mangroves and natural sinkholes—and the El Castillo, a large stone castle perched high on craggy cliffs. With beachside bars, fine dining, live music, intriguing wildlife, spas, and abundant culture in every corner, it’s a place of total awe and wonder.




Whether you’re feasting on fresh seafood, watching sunset from the seat of a kayak, parasailing high above the ocean, or jet skiing, Fort Myers is a great Floridian escape from the North’s chilling winter months. Be sure to visit the Fort Myers Brewing Company for a game of corn hole, a delicious food truck feast, and a locally brewed cold one. Take a stand-up paddleboard (SUP) out at sunrise for the ultimate meditative experience.


Other Unique Escapes:

  • Amalfi Coast and Venice, Italy
  • New Orleans, Louisiana
  • Barcelona, Spain
  • Sri Lanka
  • Senegal


Whatever your interests are, there’s a relaxing vacation waiting just around the corner. Make the most of these winter months but planning an unforgettable getaway!

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