The Top 7 Winter Trips to Book Now


Why is it that summer vacations get all the attention, all the hype? Maybe it’s ingrained in us from childhood. School’s out for summer, but school should be out for winter instead. That’s when the days are interminably long and dark, and a decadent holiday is needed more than ever. And if it can’t be two weeks in the Maldives, at least let it be two days in the Florida Keys. To that end, we’ve identified the greatest getaways for the upcoming winter. In our opinion, you’re never more warranted to splurge on a dream vacation than during the throes of a Polar Vortex. After all, in the words of Taylor Swift: ‘Tis the damn season. 

1. Escape to the Lush Rainforests of Panama

Dusk at Plaza de Francia in Panama

Dusk at Plaza de Francia in Panama City, Panama

When it rains, it pours. And when you’re in Panama, the rain pours strong enough to fortify a rainforest barricade between South and Central America (also known as the Darién Gap). But you will be grateful for that liquid sunshine when the dry season arrives in January and the tropical jungle glistens beneath that equatorial sun. And while digital nomads worldwide migrate to Costa Rica with the first snowfall of the season, Panama remains relatively undiscovered. A slice of paradise awaits you — blissfully free of crowds. 

2. Get Away From it All in the Florida Keys

Sunset view from a pier

Sunset in Islamorada, Florida Keys

In their iconic ode to vacation, there’s a reason the Beach Boys envisioned Kokomo as an island “off the Florida Keys.” Nowhere else on earth is as laid-back, as devil-may-care, as this coral cay archipelago in the south Atlantic. Though merely an hour’s drive south of Miami, the Keys feel like they belong to a separate planet than the nightlife capital of south Florida. Nicknamed the Conch Republic for its attempts at secession, Key West epitomizes the ethos: No shirt, no shoes, no problem. In the famous words of Brian Wilson: That’s where you want to go to get away from it all.

3. Walk in a Winter Wonderland in Bavaria

Christmas shops in Munich, Germany

Christmas Market in Munich, Germany (Adobe stock)

If you’ve ever felt like living inside a holiday snow globe,  book a flight to Munich post-haste — or, at the very least, before December 24th. If the Bavarian Christmas markets aren’t already atop your holiday wish list, you’re either Scrooge or simply uninformed. Even the most jaded, Grinch-like heart can’t resist the yuletide splendor that envelops the Alpine villages of southeast Germany this time of year. After all, Baroque churches and Medieval castles are best observed laden with sparkling lights atop and beneath a shimmering of snow. 

4. Bask in the Sunshine of the Happy Island of Aruba

Picnic pools on a pier in Aruba

The lunch dock at Zeerovers, a popular restaurant in Aruba

If seasonal depression is a regular (dreaded) occurrence in your life, there’s no better cure than a trip to Aruba. One Happy Island is more than just a catchy slogan for this white-sand oasis in the Dutch Caribbean — recent research has validated that Arubans are among the most happiest people on earth. And why wouldn’t they be when the sun shines upon them nearly every day of the year? Aruba is located just outside the hurricane belt — guaranteeing a forecast of near-cloudless skies and tranquil turquoise waters. And visitors who aren’t locals wish we were: Aruba has the highest return rate in the Caribbean, with 65% of guests always coming back for more. So, if you’re not yet a convert to the dushi lifestyle, we suggest embarking on your maiden voyage this winter.

5. Discover Adventure and Sophistication in Chile

Rooftop restaurant in Chile

The rooftop at the W Santiago, Chile

It’s rarely chilly in Chile. Even when skiing in the Andes in the depth of South American winter (July), the high-altitude sunshine is an eternal balm for all that ails. And the country’s capital, Santiago, is the perfect cosmopolitan escape for our colder months —  a respite from the frigid winters of the northern hemisphere. Stay at the Ritz Carlton Santiago for a taste of true Chilean luxury, and sip cocktails on the rooftop at the W Santiago to watch the sun go down over the central valley. Chile’s climate in December is warm and temperate — perfect for a Santiago sojourn — although, in January, heat waves become more common. Take that as a sign to mark an item off your bucket list and  head south to Punta Arenas, the gateway to Antarctica where temperatures rarely rise above 60° — and the Magellanic penguins never disappoint.  

6. Maximize your Bliss in The Maldives

View of an island in the Maldives from a seaplane

Islands in the Maldives viewed from a seaplane

There’s no vacation more envy-inducing than the Maldives. The vibrant aquamarine hues of the Indian Ocean are instantly recognizable — you’d identify that white-sand beach anywhere (usually in photos of your coworkers’ honeymoons). While this affliction most severely impacts the Instagram-addicted, there’s no escaping the lure of those overwater bungalows in our popular imagination. So, why even try? Resistance is futile. This winter, give in to your desire to be pampered and spoiled like an aquatic deity and book that flight to Malé — with or without a significant other. There’s more to the Maldives than luxury and romance, and this coral island chain contains a surprising amount of adventure, both above and beneath the water. Hang ten, swim with sharks and eradicate tan lines from the privacy of your plunge pool. To quote the patron saint of vacation, Jimmy Buffet: Changes in latitude, changes in attitude. After all, you’re a better person when you’re tan.

7. Go Skiing in Jackson Hole

Jackson Hole, Wyoming (Adobe stock)

Tucked away in western Wyoming, in a valley surrounded by mountains on all sides, Jackson Hole’s remoteness plays a distinct role in its allure. Its inhospitable climate and conditions—an alpine desert that receives triple-digit inches of snowfall per year—made it undesirable to settlers and Native Americans for centuries. And, as such, it remained uninhabited until the turn of the last century.  “Keep Jackson Wild” is the town’s mission statement for a good reason. You can feel this vastness still when you visit today, even though Jackson Hole is now a well-known destination. Often ranked among the best ski resorts in North America, Jackson Hole Mountain Resort boasts near-limitless backcountry and the infamous Corbet’s Couloir.  Yet, due to its remoteness (and a shortage of direct flights), this off-piste paradise remains decidedly less crowded than its neighbors to the southeast, Aspen or Vail—resulting in fresher trails and shorter lift lines. Part of Jackson Hole still feels untouched—and this sense of unspoiled nature, of wild Western possibility, extends to the ski terrain, famous for being steep, deep, and challenging.

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