17 Tips to Make Holiday Traveling a Joy

Written by Jillian Walsh

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17 Tips to Make Holiday Traveling a Joy

With school out and many businesses offering vacation time, there’s no better opportunity to have an adventure with your friends and family than over the holidays. But traveling in winter means keeping a few key things in mind, ranging from personal safety to booking flights at the right time and more.


Make the Most of Your Winter Vacation This Year with These Tips

1. Health is wealth

It’s a good idea to pack a travel health kit, including prescription medications, Band-Aids, insect repellent, sunscreen, and alcohol-based hand sanitizer for any unexpected events. Keep this in your luggage or car wherever you go, and you’ll always be prepared for minor injuries or germy hands.

2. Make sure your car is travel ready

This is the time to be sure your car is in peak condition for travel, whether you’re planning a long trip or a nearby visit. Get a complete checkup for your car, van, or truck, including an inspection of your tires, well in advance of your trip. Auto repair shops are busy at holiday times, and you may want to consider repair expenses in your holiday budget.

Map out your holiday travel route ahead of time and get to know what optional routes are available if traffic backups or weather issues cause a change in plans. If traveling with children, be sure to pack plenty of snacks and water to keep stops to a minimum. Travel games, videos, and activities for those confined to car seats can make the trip smoother.

3. Check weather sites for travel advisories

You may be excited to spend winter in the snow, but before you go you should check local and national weather sites for travel advisories regarding your driving route, upcoming flight, or other vacation plans. The last thing you want is to be stuck on the road in dangerous conditions or get to the airport on time for your flight, only to find out that it’s been canceled due to an incoming snowstorm. The sooner you are warned about travel advisories, the easier you can change your plans and still have a great holiday vacation.

4. Pick the right destination

There’s more to traveling smartly during the winter and holiday season than focusing on safety, of course. You should also pick the perfect destination well ahead of time.

Is it your holiday tradition to visit friends or family members? Your choice is an easy one! But if you have more freedom and flexibility for your holiday plans, try to research popular holiday destinations based on factors like:

Having an idea of where you’ll go over your winter vacation ahead of schedule will make it easier for you to buy tickets and plan your trip with minimum hassle. And choosing more affordable places to travel will free up your budget for other holiday expenses.

5. Book pet care well in advance

Have a dog (or several)? They’ll need to be looked after while you are away. Like when booking many things over holiday vacations, it pays to book pet sitters or boarding venues well in advance. One of the top holiday travel tips for pet owners is don’t wait until the week before your vacation begins to call the kennel, as many other pet parents will have the same idea. Local boarding facilities might not have any space left, or pet sitters may already have full schedules.

Instead, book pet sitting or dog boarding a month in advance or more.

6.  Reserve restaurants in advance, too

By the same token, try to reserve any restaurants you want to eat at in advance of your arrival. Many of the hottest dining destinations around the country and around the globe offer reservations during busy holidays weeks or months ahead of time. The more popular the place, the earlier you need to reserve your table.

7. Renew your passport ahead of time

Depending on when you last did it, your passport may need to be renewed. Be sure that your passport, driver’s license, and other documentation won’t expire while you are on vacation. That’s a setup for a travel disaster, where you might be stuck in one country or worse, not be allowed to board your flight because of a documentation issue.

Packing up suitcase for vacation and preparing for a journey, flat lay

8. Pack light if you have access to a washer & dryer

If your holiday vacation destination has a washer and dryer for your clothes, don’t bother packing dozens of different outfits. Instead, pack light; your bags and your shoulders will thank you. Once you reach your vacation home or hotel, you can wash the clothes that you traveled in and cycle through the different outfits you’ve packed for the adventures ahead.

9. Do a winter car check before hitting the road

Planning on driving to your vacation destination? You need to make sure your car is up for the task. That means performing a standard winter readiness check, including:

One more thing – it’s a good idea to pack an emergency kit in your car just in case you get stranded in the snow. Make sure your car has a few flashlights, some blankets, and bandages or first-aid supplies at a minimum.

10. Seriously, consider travel insurance

If you’re like most Americans, some types of insurance feel like little more than attempts to get you to spend money you don’t have to. But when it comes to holiday travel, travel insurance really is a good investment.

With COVID-19 strains still floating around, and with the possibility of unpredictable winter weather always looming ahead, it may be worth it to purchase travel insurance for your plane tickets or other major travel bookings. The right insurance policy will refund you in part or in full if your plans change, if you have to cancel your vacation plans less than 24 hours before departure or if your flight is canceled by your airline.

11. Consider being a contrarian traveler

As you initially plan your winter vacation, you’re probably thinking of the standard range of holiday destinations: Florida, the Bahamas, and other warm-weather sanctuaries where you can get away from the cold for a few days.

But if you’re wondering how to afford travel during the winter months and enjoy a more novel experience, consider roaming the globe as a contrarian traveler instead. For example, many plane tickets to Europe and other cold-weather destinations are available at discounts around the holiday season – many Europeans and tourists alike don’t think of heading up north when planning their winter vacations, after all.

You can take advantage of those discounts and enjoy snowy, seasonal adventures in destinations like Prague, Rome, Salisbury, and Reykjavik –  Iceland is a perfect place to catch the aurora borealis around the holidays.

Being a contrarian traveler as you decide where to travel in December and January is a lesser-known travel tip that may grant you special experiences and opportunities you’d otherwise miss if you stick to the standard holiday vacation script.

12. Plan your route (& backup route)

The best winter road trips are ones that go exactly as planned. So it’s a no-brainer that you should plan your route down to the finest detail. Figure out when you’ll leave home, what roads you’ll take, and what traffic and the weather will be like.

While you’re at it, consider planning a backup route or two, as well. For example, if you’re going to a grandparents’ cabin in the mountain, make sure you know how to get there in at least two ways – if one road is snowed in or hasn’t been plowed, you can make a quick adjustment and get back on your way.

13. Pack a physical map

Winter tends to play havoc on our electronic devices, including car GPS systems. If your phone or car loses its signal, you could find yourself stranded in the middle of nowhere. Do yourself a favor and pack a real map to put in the glove compartment. If the worst happens, you can navigate to the nearest clear road the old-fashioned way!

14.  Consider Amtrak for domestic travel

If you’re visiting family or a holiday destination in the US, don’t lock yourself into flying if you don’t have to. Amtrak travel can be surprisingly cost-effective and very fun. That’s because Amtrak fares are determined solely by how far in advance you purchase your ticket as opposed to seasonal shifts, so there’s no holiday upcharge to worry about.

Taking the train can be a relaxing experience and a fun adventure for your kids. Depending on your route, you could be treated to snowy landscapes on your journey: perfect for snapping photos and taking in the holiday ambiance.

Ordering Christmas presents, online payment. Online shopping, internet banking, spending money, holidays, vacations concept

15. Always book tickets with your credit card

Whether you’re booking tickets for a plane, train, or automobile, be sure to do so with your credit card instead of your debit card. That way, if you have to cancel at the last minute and need that extra cash ASAP, you won’t have to wait a few business days for the money to hit your checking account.

On top of that, scams and identity theft are more common during the holidays, as people shop online and purchase travel tickets more frequently during this timeframe. Purchasing tickets with your credit card will help protect your identity and your primary bank account from potential thieves.

16. Wrap gifts after you arrive

If you’re bringing presents to friends or family members for the holidays, do yourself a favor and wait to wrap your gifts after you arrive. Pack the wrapping paper, tape, and other accessories with your clothes (and don’t forget the gifts themselves!). This will not only save space in a car or suitcase, but if you are flying, TSA may require you to unwrap all your gifts and your hard work!

When you finally wrap your gifts, you don’t have to worry about them being damaged or torn in transit.

17.  Be social – ask locals what’s good to see & do

No matter where you go for your holiday vacation, you’ll want to enjoy the unique experiences in that area. Hotel concierges, taxi drivers, and other locals know exactly where you should go and what you should see so a top winter holiday travel tip is just to ask for their suggested spots. Plus, they can give you recommendations based on your budget or preferences, whether you’re looking for twinkling lights in a winter wonderland or budget-friendly festivities like free Christmas tree lightings and holiday markets

Be social and ask questions! In many cases, locals are the ones who can give you the best tips about lesser-known hotspots, saving you from less-than-stellar experiences at tourist traps.

Bon Voyage!

Traveling in winter can be tough, but it can also be fun if you plan ahead and prep for the weather, using our holiday travel tips and others. To have the best winter vacation possible, set your travel budget or take out a vacation loan now, before you pack your bags, so your financial ducks are all in a row by the time you hit the airport. Have fun!



  1. https://wwwnc.cdc.gov/travel/page/traveling-holidays
  2. https://www.redcross.org/about-us/news-and-events/news/Travel-Safety-Tips-for-Thanksgiving-Travelers.html
  3. https://www.travelchannel.com/interests/travel-tips/photos/tips-for-traveling-during-the-holidays
  4. https://www.citizensbank.com/learning/holiday-travel-tips-for-your-sanity-and-wallet.aspx


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