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The 12 Mistakes of Holiday Travel and How to Avoid Them

Travel Team | Sep 8, 2023

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Snow covered airplane parked at the airport.

Whether it’s New Year’s, Easter, Diwali, or Thanksgiving, holidays are something to look forward to. This is especially true when your celebrations include travel. If you dread planning holiday travel, however, it might be because you're making one (or more) of these common mistakes. Thankfully, we have the best travel hacks that can help you avoid these missteps.

Common Holiday Travel Mistakes and How to Fix Them

Mistake #1: You don’t book in advance.

Women wearing traditional head wraps waving sparklers.

Spontaneous trips can be incredibly exciting! But the holidays are not the time for those unplanned getaways. Flights and hotels will be packed, and the closer you are to the holiday itself, the more expensive reservations are likely to be. That’s if you can get a ticket at all.

Peak winter holiday travel in the United States — around Thanksgiving and Christmastime — should be booked sooner rather than later. As we said in our holiday travel guide, aim to book by the end of October for the best deals on flights and many other accommodations.

Mistake #2: You forget “obvious” travel tasks.

Holiday travel can create the perfect storm of forgetfulness. You’re wrangling everything you need for the celebrations at the same time you’re trying to pack, arrange a house sitter, finish a project at work before you leave, and a thousand other things.

Long before things get hectic, start a list of all the logistics you need to take care of so you don’t forget something “obvious” like renewing your passport or notifying your credit card company you’ll be out of town. If it helps, run your list by friends or family to see what you might have forgotten.

Mistake #3: You travel at the wrong time.

Sometimes we’re limited with when we travel. But if you can be flexible and travel outside peak times — on the Monday before Thanksgiving instead of Wednesday, for example — you'll save yourself a lot of headaches.

Additionally, paying to fly at a convenient time can be a lifesaver. For instance, booking a red-eye flight with two transfers might be the cheapest option, but it might not be the best. More connections mean more opportunities for delays and lost luggage. And if you have kids in tow, booking a direct flight could be well worth the investment. Before you book anything, be honest with yourself about what your family — and your budget — can handle.

Mistake #4: You overschedule.

Jam-packed schedules can create undue stress, especially when something inevitably changes your itinerary. Work with your family or traveling companions to prioritize the traditions that are truly essential, making sure to build in downtime when everyone can rest and regroup. By focusing on just a few key activities, you’ll have time to make memories with your loved ones, rather than trying to rush everyone from one task to the next.

Man rushing from airport to corporate holiday party.

Mistake #5: You don’t give yourself enough time.

Even with extra time built in, it’s important to keep your itinerary flexible. Allow time to take advantage of serendipitous activities or mornings when everyone just wants to laze around together.

Just as importantly, a flexible itinerary also means you’ll be less stressed when flight delays and cancellations, construction roadblocks, and bad weather force you to alter your plans on the spot. Remember that the line at security, the wait for food at the restaurant, the amount of time it takes to get everyone dressed and out the door inevitably takes longer during holidays.

Mistake #6: You abandon all routine.

It’s hard to stick to a normal schedule or an eating regimen during holidays. By all means, enjoy the unique opportunities the season brings. However, try to maintain as many of your comforting rituals as you can. It could be that moment in the morning alone with your coffee, an exercise routine, or reading a book. Finding moments of normalcy, even if that means you have to excuse yourself from the group for an hour, can help you stay centered. And when you’re centered, everyone will enjoy the holiday more.

Mistake #7: You overpack.

Lugging bulky suitcases and overstuffed gift bags is enough to make anyone grumpy. And when you’re traveling by plane, bus, or train, checking extra bags can put a dent in your holiday travel budget. Save yourself the hassle and travel light.

Focus on basic, durable staples that can be mixed and matched into entirely new looks. Jeans, solid-colored sweaters, button-downs, and scarves are great for this. If you have access to a washer and dryer at your destination, it’s even better.

If you’re traveling for a gift-giving holiday, an easy way to lighten your luggage is to ship presents to their recipients, either via the online retailer you bought from or by dropping them at the post office before you leave town.

Mistake #8: You think gifts have to be things.

While we’re on the subject of gifts, it can work to your advantage to rethink your gifting strategy to start with. Instead of giving trinkets and baubles, consider giving someone the gift of an experience. The trip itself might be your gift. You could treat your host to a nice dinner when you arrive. Or you could give them a card telling them about the dance lessons you signed them up for.

Mistake #9: You expect too much togetherness.

It’s often a given that you’ll spend time with family during the holidays. You should absolutely embrace the spirit of togetherness and create memories together. Remember, though, that there is such a thing as too much quality time.

Take advantage when family or friends offer their spare room or couch to save money on a hotel. However, also be realistic about what you need. If their home is too small for you and your kids, it might be worth the extra expense of renting someplace. After all, if that saggy couch results in bad sleep and that means you’re grouchy and pick a fight, was it really that good of a deal?

Gerbil's eating snacks.

Mistake #10: You don’t pack snacks.

“There will be plenty to eat when we get there,” sounds logical, but it can be a trap. Showing up at your destination hangry or with a dehydration headache is not how you want to start your holiday vacation. While there might be treats and hors d’oeuvres when you get there, throw a few healthy snacks in your bag to hold you over until then.

Mistake #11: You don’t have a realistic budget.

As you start to plan your holiday travel, be very clear about how much you are able to spend and how much things will cost. It’s easy to break the bank during the holidays, and even easier when you’re traveling. Set your priorities, and if the act of travel is more important than the gifts or big meals your companions are used to during the holiday, be honest with them about how you’re willing to spend your money. Not sticking to your budget — or not having one in the first place — is a surefire way to regret your finances later.

Mistake #12: You don’t get the best travel insurance.

Traveling on a budget doesn’t always mean cutting as many corners as possible and finding the cheapest version of things. Because so many things can go awry with holiday travel — overbooked flights, icy winter roads, a family feud that causes you to reconsider traveling at all — it’s as good a time as any to protect your trip with travel insurance.

Trip protection plans can provide coverage for travel delays and cancellations, lost or damaged luggage, and more. And if your holidays are taking you abroad, you’ll want to consider travel medical insurance in case you get sick or hurt while traveling.

Happy Holiday Travels

With all that goes into planning the perfect holiday trip, it doesn’t take much to suddenly feel overwhelmed. Fortunately, buying travel insurance from licensed agents can make some of that easier. Talk to our experts about finding the best travel insurance for your trip and enjoy the celebrations with the knowledge that you’re well protected.


Former Seven Corners writers Grace Lower and Luke Maguire Armstrong shared some of the holiday tips and memories for this blog.

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