10 Tips on How to Have a Winter Vacation: A Guide For Traveling in the Cold Season

Planning a winter vacation can be a little tricky. It’s one thing to throw a swimsuit and some shorts in your bag for a summer beach trip…but planning a cold-weather adventure is quite another story.


But don’t worry - we have 10 fantastic tips to help make your winter vacation a breeze!


Winter vacation



1. Research Your Accommodations

It’s always wise to take a good look at where you’ll be staying, but it’s even more critical during the wintertime. Make sure you’ve double-checked essential details like:

  • Will bedding be provided?

  • Is there heat? (Looking at you, rustic mountain cabin)

  • Do you need 4-wheel drive to access it when there’s snow?

  • Is it close to things you want to do?

  • Will you be able to stock up on or have easy access to food if you’re snowed in?

Yellow cabin in a gloomy day in the middle of the mountains

Few people like these kinds of surprises, so make sure you know what you’re getting into before you book.


2. Add on Travel Insurance

Some people swear by travel insurance, and others prefer to take their chances. However, traveling during the winter definitely increases those chances due to ice and snow. Most basic travel insurance packages protect you against bad weather cancellations, significant travel delays, and even alternative transportation costs.


If you don’t want a comprehensive package, there are always options that you can customize for your specific vacation. For example, add skiing or snowboarding insurance to your mountain resort trip to cover injuries and/or booking cancellations.


3. Pack a Hard Shell Suitcase

Winter trips are an excellent reason to buy a hard shell suitcase if you don’t have one in your travel arsenal. Besides containing all your bulky winter clothes into a defined space, hard shells also protect your belongings from all the cold wetness that the season brings.



4. Be Smart About Storms

Winter storms affect all forms of travel, but drivers need to be extra cautious this time of year. Keep an eye on the weather along your route, so you have a heads up if something bad is coming your way. And if there is any chance you’ll be driving into (or near) storms, it’s always best to stay off the roads until they pass.


City bus on the side of an empty street in the middle of a winter storm

However, in case you get hit by surprise, be sure you have cold-weather necessities prepared, including an extra tank of gas, warm clothes, fully charged phones, and even emergency flares. It’s better to be safe than sorry!



5. Book Activities Ahead of Time

If you’re planning to fill your schedule with any winter activities, it’s always wise to book your time slots well in advance. Especially at places like resorts, where everyone is there for the same things, reservations can fill up fast! It never hurts to plan ahead but waiting until the last second may mean missing out.


Large crowd in a ski resort - winter destination


6. Try Taking the Train

If you’re worried about a holiday rush or just don’t like the hassle of driving or flying, why not give train travel a go? Most trains offer comfortable and relaxing seating for your trip, and you can even book overnight accommodations for longer excursions. Plus, you can simply sit back and enjoy the entire trip with easy access to food and restrooms the whole way.

One more bonus: train baggage limits are often much more lenient. For example, Amtrak lets you bring two 50-pound suitcases for free, making it significantly easier to pack those winter clothes and even presents.


7. Don’t Overpack

“If I have the space, why not bring it?” Because then you have to carry it and repack it! Be conscientious about your winter wardrobe and stick to the essentials for your trip. Especially with airlines, over-packing can mean hefty fees, so packing light is your best option. Pick items that are warm but not bulky and that you can wear multiple times in different combinations if necessary.


Woman carrying folded warm clothing for the winter

P.S. If you book your activities in advance, you’ll already know what counts as essential, and you can cull unnecessary coats, boots, and gear.


8. Have Backup Plans

‘Tis the season of canceled plans, so always have a plan B. Bring games to play indoors if your outdoor plans get snowed out, and keep an eye on other flights to your destination if yours gets canceled or heavily delayed. You may even have a secondary location in mind in case yours becomes suddenly inaccessible. Don’t forget to read the cancellation policies for each part of your trip so you can maximize refunds and put them toward your plan B.


9. Fly Nonstop Whenever Possible

Have you noticed that weather always seems to hit while you’re at a connecting airport? Cut down your chances of being stuck mid-route by booking non-stop flights whenever you can. If your flight gets delayed from your hometown, you can simply return home and wait it out. And if it happens on your return trip, there’s a good chance that the place you


10. Choose the Right Vacation for You

Large crowd in a skating rink with national flags in the view

Traveling during the winter doesn’t mean you have to go someplace with snow! If you hate being cold and trekking through snow, don’t cave in to pressure to stay at a ski resort or mountain cabin. Conversely, you don’t have to find an idyllic tropical paradise to escape the cold and get those perfect social media pics.


Think of the kind of place that would make you the happiest during your trip and do your research to see what’s available within your time and budget range.



Where will you go this winter? No matter what your winter destination is, make waiting for your trip more fun by using our Vacation Countdown App!


Available at the App Store or Google Play Store.

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