Holiday Vacation Destinations You've Never Thought Of

While traveling in the summer provides many options to soak up the sun, winter can be a challenging time to know where to travel, especially if you’re not into skiing and winter sports.

And yet winter can be a great time to travel for many reasons.

Reasons to Travel in Winter

If you have flexibility about when you travel, consider going in the winter. Prices are much lower off-season, and sometimes you can get upgrades without paying for them. There are, of course, fewer crowds since the summer months are when most people travel. And if being around crowds stresses you out, how relaxing is a summer vacation anyway?

And while you can visit destinations that are temperate year-round, likely no destination will be boiling the way it is in summer. And it’s a fact: snow makes everything look magical, so your photos will be gorgeous! Finally, you may encounter fun holiday markets and events that can enhance your trip even more.

There are, of course, a few drawbacks to traveling in the winter, the biggest one being unpredictable weather. When snowstorms hit, flights are delayed or canceled, which could put a big kink in your plans. 

Let’s look at a few of the destinations you might want to consider for your next holiday vacation.

For Christmas Fans: Esslingen, Germany

Located just 10 minutes by train from Stuttgart, this bedroom community is the epitome of quaint, old-school Germany. Its timbered houses, painted in cheery pastels, give the town a fairy-tale vibe.

There’s an annual Medieval Market & Christmas Market held from late November until just before Christmas. You’ll find 200+ vendors offering local delicacies, medieval merchants and craftsmen, tours, and workshops. You’ll feel like you’ve stepped back in time even more when you see people dressed up in medieval garb (which you can also buy for yourself at the market, in case you forgot to pack your kirtle!).

For Warm-Weather Lovers: Key West

If bundling up for your winter holiday doesn’t appeal, consider a trip to the temperate Florida Keys. Key West, the last of the Keys, has temperatures ranging from 65 to 80 in the winter, which means you can still rock flip-flops and shorts on Christmas.

There are several Christmas-related parades and events in town in December, as well as the usual year-round offerings of sunset boat tours, bar crawls, and beach time.

If you’re there for New Year’s, don’t miss the Conch Shell Drop on Duval Street or the New Year’s Eve Shoe Drop Celebration, which is your opportunity to watch a six-foot-high red high heel descend from Bourbon Street Pub New Orleans House!

For Winter/Nature Lovers: Kakslauttanen, Finland

If seeing the Northern Lights is on your bucket list, you won’t find a better spot to view them than from your own igloo at Kakslauttanen Arctic Resort. The glass igloos give you an unobstructed view of the lights above. Bring your camera!

Additionally, you can enjoy husky, reindeer, or snowmobile safaris, aurora hunting, or cross-country skiing.

For Spa Lovers: The Dolomiti Mountains, Italy

While Italy is chock-full of beautiful places to visit (like the Amalfi Coast), one that might not be on your list is the Dolomiti mountains, located north of Venice. For those who prefer the après-ski more than the actual exercise, staying at a spa resort in Italy’s Dolomiti mountains could be the perfect balance.

In towns like Cortina D’Ampezzo, Alleghe, and Mareson-Pecol, you’ll find hotels with spa amenities. QC Terme Dolomiti is a great example. Here, you can enjoy massages, a thermal water path, and heated pools. 

And if you’re traveling with skiers, there are plenty of slopes nearby to enjoy while you get a massage! Whether you ski or not, you’ll appreciate how gorgeous the mountains look draped in snow.

For Those With Kids: Orlando, Florida

Yes, Florida graces this list twice. If you have kids, you already know that Orlando is the epicenter of all things Disney (and Universal), and there are plenty of holiday events at the theme parks here. 

And yes, I’ll backtrack a little about avoiding crowds because Orlando does draw a healthy number of visitors over the holidays. But there are also fun things to explore outside of the theme parks. For example, Marriott’s Gaylord Palms hosts an annual holiday event called ICE! That changes each year but always includes ice sculptures, slides, and tunnels that appeal to kids of all ages. The weather may be warm outside, but bring a coat to experience ICE! Since the venue is kept cold.

If you want to explore more of Orlando, there is also the beautiful Lake Eola Park at the center of downtown, as well as the Orlando Science Center for science lovers.

For History Buffs: Malta

This island, which sits just south of Italy and north of Tunisia in Africa, is a hidden gem. With gorgeous beaches you can enjoy throughout the year, Malta is a great destination if you hate the cold.

In addition to being a gorgeous place to chill on the beach, it also has a rich history, thanks to being invaded over the millennia by the Phoenicians, Carthaginians, Romans, Arabs, Normans, Aragonese, Crusaders, French, and British.

Visit more than 90 museums and landmarks, national monuments, and underwater sites, including Ħaġar Qim and Mnajdra Archaeological Park, where you can walk among 5,000-year-old ruins.  Or, if you’re a diver, explore the Xlendi Underwater Archaeological Park, home to a Phoenician shipwreck from the 7th century BC.

Tips for Traveling for the Holidays

Now that you’ve reviewed this list of unusual winter vacation destinations, which appeal to you? Ready to start planning your trip? Here are some tips to help you have the best winter vacation ever.

Be Strategic About Booking Flights

Book your tickets about six weeks in advance. You can use tools like Hopper or Kayak to track flight prices and get the best deal (Hopper will tell you if prices are likely to drop and when the best time to buy is). 

If you don’t mind flying on the holiday, Christmas Day is often a cheap and uncrowded day for flights. Keep in mind that the day before and the day after Christmas are often busier for flights, so you might want to avoid booking a flight on these days.

Weather

Keep an eye on the weather, as a snowstorm, either at your destination or where you have a flight layover, could demolish your plans. Consider purchasing travel insurance if your flight or hotels are otherwise nonrefundable. And remember, if you do find yourself stuck in an unplanned location, remember travel hack #15: be open to serendipity!

Also, plan for contingencies. I traveled to Europe the year it had the worst winter weather in 70 years. We were pulling our suitcases through knee-deep snow. Trains were delayed. Not fun. In the event that you can’t get out to do many activities, have a list of indoor activities you can do instead.

Events

See what events are happening where you’re headed. The holidays are usually full of fun events, and some may attract thousands of people to the place you’re visiting. If you’re interested in attending the event, book your hotel far in advance. If you’d rather avoid the crowds, note when big events are happening and book before or after.

If you’re renting a car, arrive early for big events to find a good parking spot. Consider taking public transportation as an alternative.

Traveling in winter, especially for the holidays, can be an affordable option to see a place without the crowds and the heat. Just remember that you can’t always predict the weather, so pack and plan accordingly!