Top 10 Winter Vacation Spots

Now is the time to start planning your winter getaway

Summer is winding down, and as the temperatures begin to drop, it becomes the perfect time to start thinking about a winter vacation. Maybe you’re seeing the last good pool and beach days slip away and are looking forward to the days when you can escape the winter cold to a sunny locale. Or perhaps you’re looking forward to a snowy retreat where you can ski during the day and curl up next to a fire at night. Whatever your preference, you’ll save money and have a good shot at the top hotels and resorts if you book early.

This month, BOSS looks at 10 of the best winter vacation spots for everyone from snowbirds to beach bums (five in the US and five abroad).

Top 5 U.S. Winter Vacation Spots

Jackson Hole, Wyoming

Skiers and snowboarders across the globe flock to Jackson Hole during the winter months for its world-class skiing. With resorts such as Snow King Mountain Resort, Jackson Hole Mountain Resort, and the Grand Targhee Resort offering a comfortable stay, skiing and snowboarding, thrill rides, scenic tram rides, wild animal sighting, and more, it’s easy to see why Jackson Hole is one of the premier winter vacation destinations in the US.

Just north of Jackson Hole is the National Museum of Wildlife Art, a 51,000 square foot museum featuring works by Rembrandt, Picasso, Georgia O’Keefe, Andy Warhol, and others.

Key West, Florida

Those looking to head south for the winter can’t get any farther south in the continental US than Key West. Winter is high season due to the 75-degree weather, but that just means the crowds on Duval Street will be reveling all night at the historic Sloppy Joe’s Bar and other hotspots. The diving, snorkeling, fishing, and boating are excellent, but no one would blame you if you spent much of the day lounging pool side at the Galleon Resort or Ocean Key Resort & Spa.

It’s worthwhile to set some time aside to visit the Hemingway Home & Museum, which is also home to several dozen six-toed cats, some of whom are descendants of the novelist’s own six-toed cat, Snow White.

New Orleans, Louisiana

You won’t get Mardis Gras in the dead of winter (it’s Feb. 25 next year), but you won’t get an overcrowded Bourbon Street either. The weather will be temperate as you stroll through the French Quarter, pop in to jazz clubs such as Preservation Hall and the Spotted Cat, and sample local cuisine from Commander’s Palace, Beachbum Berry’s Latitude 29, and Herbsaint.

Lodging in the heart of the city can be found at world-class hotels such as the Ritz-Carlton and the Royal Sonesta. Additionally, ghost tours and cemetery tours are available for those with a fascination with the supernatural, as are bayou tours for nature lovers.

Breckenridge, Colorado

A top destination for skiers and snowboarders, the Breckenridge Ski Resort boasts 2,908 acres of mountain peaks, with trails and terrain parks for all levels of snow sport enthusiasts. Don’t miss the Imperial Express, North America’s highest chairlift that gives unparalleled views of the mountains and city.

When not hitting the slopes, head into town to relive Breckenridge’s Gold Rush history as you explore Main Street’s Victorian buildings that are now some of the area’s finest restaurants — including Hearthstone, which offers fresh and sustainable meals in a historic house with galleries and shops.

Maui, Hawaii

Not as rustic as Kauai, yet not as developed as Oahu, Maui offers scenic beaches, hiking trails, surfing, snorkeling, diving, and much more. Whether you stay at Ka’anapali Beach Resort, the Wailea Beach Resort, or more rustic lodgings along the Road to Hana, the beach and breathtaking views are not far away. Set some time aside to wake up early and trek up Haleakala to watch the sunrise above the clouds and then ride a bike down Maui’s 10,000-feet high volcano.

With Southwest Airlines recently beginning flights to Hawaii, it’s become easier to find cheap fares to the Aloha State. An added bonus: Winter is the perfect time to visit Maui for those looking to catch the humpback whale migration.

The Top 5 Global Winter Vacation Spots

Lucerne, Switzerland

The picturesque city set on Lake Lucerne is beautiful any time of year, but in the winter it comes alive with festive lights and Christmas markets, especially in Weinmarkt and Renaissance Altes Rathaus in the pedestrian-friendly Old Town. Of course, skiers will not want to miss the chance to conquer the famous nearby peaks of Rigi and Pilatus.

When you decide to step inside to avoid the cold, you can explore Lucerne’s Rosengart Collection, taking in its pieces by Picasso, Paul Klee, Matisse, Monet, and more.

Costa Rica

Forget all about winter weather with an escape to the pura vida of Costa Rica. December marks the end of the rainy season, making it a perfect time to zipline through the rainforest canopy, hike the Arenal Volcano, or visit the La Paz Waterfall Gardens. Visitors can choose to rough it on the beach or stay at popular resorts such as Playa Cielo or the Tulemar Resort.

Wherever you stay, spending time on the beach and in the ocean snorkeling, diving, or surfing is a must when visiting Costa Rica.

Whistler, British Columbia

A winter trip to Whistler — about 75 miles north of Vancouver — is sure to involve a lot of time at Whistler Blackcomb, the massive ski resort that boasts almost 40 feet of snow per year across its 8,100 acres. When taking a break from speeding down the slopes, visitors can watch some of the numerous ski and snowboard competitions held at Whistler every year.

In addition to skiing and snowboarding, visitors can go snowmobiling, snowshoeing, and catch a scenic ride on the PEAK 2 PEAK gondola.

Dubai, United Arab Emirates

Spend your winter break in a desert oasis where daytime temperatures range from the mid-70s to mid-80s. Dubai is a land of extravagance, boasting the world’s tallest tower (Burj Khalifa), massive resorts, expensive sports cars, and the Gold Souk — one of the largest gold jewelry markets in the world. The Persian Gulf’s Jumeirah Beach is a popular place to soak up some rays or play on the water.

Visitors should be sure not to miss the architectural wonders of Dubai, ranging from the modern Burj Al Arab to the historic buildings in the Bastakiya Quarter. Top of the line accommodations can be found at resorts such as the Four Seasons Dubai at Jumeirah Beach and Atlantis the Palm.

Canary Islands

Formed millions of years ago by volcanic eruptions, the archipelago making up the Canary Islands is rife with outdoor activities and good weather all year. It may seem like a remote destination, a chain of islands off the northwest African coast, but major airlines such as American Airlines and British Airways have flights to this winter vacation hotspot.

Visitors can hike among the black volcanic rock of Mount Teide, find spots for mountain biking or rock climbing, or participate in any variety of water sports from scuba diving to kite surfing. A visit to Siam Park, voted the No. 1 water park in the world six years running, is a popular choice for cooling off.  For the less outdoorsy, cities and towns such as Santa Cruz and Puerto de Mogan offer local culture, shopping, and numerous dining options.

Pack Your Bags

Whether you’re looking to stay close to home or embark on a globetrotting adventure, there are plenty of excellent options for a winter vacation that will provide a much-needed break and leave you recharged when you return to the office. Just remember, now is the time to start planning if you want to get the best rates and secure lodging at the hottest hotels and resorts.