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Holiday Travel 2021: What You Need To Know
Updated: November 17, 2021 |
Taylor Kovar, CFP

Budget Travel Tips: Holiday Travel Without Stress

Travel. Is. BACK!

For some, that’s the best news ever. After almost two years of lockdowns and quarantines, there’s a sense that we can finally go where we want, when we want. You can take the trip you postponed; go see the family across the country you’ve been missing. This also means the stress of holiday travel is about to rear its frightening head, reminding us all of the endless lines at security checkpoints, the lack of legroom in coach, and the ceaseless cries of “Are we there yet?” from the backseat. 

Holiday travel is back. You have no excuse not to go see your in-laws this year. Time to dust off your suitcases and get prepared.


Bustling Airports

Traveling during the holidays is one of those ill-advised requirements of life. We must go to see family, we must go find Santa, we must use these days off from work to get trapped in an airport for thirty straight hours.

If you forgot that flying in December is usually the opposite of fun, this year could be the perfect thing to jog your memory. If you think there’s a trick that will allow you to avoid the crowds, you’re either deceiving yourself or you need to let me know ASAP. 

Two reasons why this year will be as bad as any year that came before it.  

International Travel Resumes

This might not relate to your destination, but it’s important to know that people from dozens of countries had been barred from flying to the U.S. until just weeks ago. It’s not like foreigners couldn’t travel here by any means, but getting into our airports has not been easy. 

Now that those COVID-related travel restrictions are gone, I expect every airport with an international hub to see a lot more traffic on a daily basis. This comes during the holiday season when ports of travel will already be overwhelmed by domestic travelers. Even if you’re flying from Dallas to NOLA, folks traveling from Argentina to Martha’s Vineyard might have something to say about whether or not your flight leaves on time. 

It’s great that we’re opening back up to visitors and Americans living abroad. It’s also going to make for some pretty long lines outside the bag checking area.

More People With Freedom To Travel

This one is a little more speculative, but I’m pretty confident we’re going to have an extra wave of flyers this winter made up of those who either work remotely or retired early. Beyond the layoffs, a lot of people just opted into different employment circumstances during the pandemic. People left jobs at restaurants to start doing freelance work, or chose to take a pay cut and go remote full time. 

I have friends who, even while making less money, started traveling twice as much once their jobs no longer required them to come into the office. Having the ability to fly on a workday creates a whole new kind of flexibility, and with holiday flights readily accessible for the first time in almost two years, I bet we’re going to see some newbies in the air. 

That means even those off-peak options, like the redeyes and early morning flights, could book up more quickly than they have in years past.

Whoever it is making your check-in line move slowly—international travelers or freelance workers—the point is to be ready. Get to the airport early, have snacks and distractions ready for the kids, and wear comfortable shoes. 


To Insure or Not To Insure?

The debate over whether or not a person should pay the airline for travel insurance has raged on for years. In a lot of ways, this boils down to a Spender versus Saver argument. “What’s an extra $30 dollars if it means our trip is protected?” versus “Why the heck would we spend $30 PER TICKET if we don’t need to?”

Let’s do a quick, basic, surface-level pros and cons list.


  • Flexibility to change your itinerary
  • Protection from weather-related cancelations
  • Nominal fees


  • Policy coverage varies
  • Tickets often non-refundable
  • Purchase already insured through credit card

None of these reasons is universally applicable, which is why you’ll get different opinions from different advisors. Personally, I don’t like buying something that feels like it’s a price hike without much value. I get the feeling that the airlines won’t be that eager to help me out with any changes even if I do have insurance, so I prefer to trust my credit card and then do my best to avoid whatever circumstances might disrupt my travel plans. 

That said, I think the COVID situation makes it worth giving travel insurance a little more consideration. Especially if you’re packing up the whole family for a long flight, you don’t want a positive test to cost you hundreds on four or five tickets that can’t be exchanged. 

Different airlines handle rescheduling and COVID policy in different ways. Before shelling out any money for insurance, check out the company website and see how much information you can get. A lot of times the language is intentionally vague, in which case it’s probably worth jumping on the phone and sitting through fifteen minutes of hold music so you can ask a direct question. 

Like it or not, companies rely on our ignorance for a large portion of their earnings. Whether that’s buying insurance you don’t need or not having insurance when it could be useful, airlines are always angling for whatever will line their pockets. Don’t get scared into buying coverage that isn’t useful, but don’t assume you’ll be able to get a refund or a voucher should something come up.

Cancellations and Craziness

More than anything else, I predict the holiday season of 2021 will be defined by this. Cancellations and craziness. The airports are going to be crazy. If we get hit with a winter storm a few days before Christmas, the number of canceled flights will be enormous. 

Staffing shortages have been a problem affecting flights all year, and I can’t imagine that will stop right in time for Christmas. Even if every airline goes on a hiring spree, it’s still the season when people want time off work. It’s also the time of year when everyone is getting sick, and people aren’t going to show up to work with a cough when their place of work is on an airplane.

This is why we all need to be more diligent than normal in planning our trips.

Aside from making sure you’ve got all your bags organized so you can make it through security unscathed, you need to have clear plans for how you’re getting to the airport, where you’re staying after, and what each of those places requires. 

For example, a lot of hotels still aren’t running airport shuttles in the aftermath of the pandemic. A lot of parking lot shuttles still aren’t running either. If you have three kids and a dozen bags, an Uber to or from the airport isn’t going to work for you. Confusing matters even more, a lot of hotels do have shuttles running but haven’t updated the COVID verbiage in their contracts. A call to the front desk of these places might be the only way to know what’s really going on. 

Once you get to where you’re going, make sure those rental cars are secured with all the add-on you need, like car seats and cargo space. More travelers = more rentals = more renters running out of supplies and not having what you need. Don’t take anything for granted.

The Great Holiday Escape of 2021 is going to be awesome. People will be reunited with family; they will take their young children places they’ve never been before; they’ll break out of the routines that have us nearly bored to death. 

None of it will be easy.

Even the most seasoned, prepared traveler will have to contend with cancelations and craziness. If your trip ends up being relatively painless, that’s great news; we still recommend you plan for the worst. 

Whatever your holiday plans might be, we here at The Money Couple hope you get where you want to go and have a wonderful time while you’re there!

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