14 Tips and Tricks For Avoiding Holiday Travel Headaches

I was just asked to do an interview forNewsNation Live on how travelers can prepare for a smooth trip this holiday season (video embedded below). If you recall, last year was anything but smooth when Southwest Airlines ruined Christmas for millions of travelers, cancelling over 14,000 flights. You know it was bad when even some of their own pilots and flight attendants had to sleep in airports. RELATED: 10 Tips for Passengers Caught Up in a Meltdown

There were a lot of factors that lead to that epic failure and fortunately, I think the airlines have learned from Southwest’s mistakes, which included overscheduling planes and crews. The proof was that there were very few cancelations and delays this past Thanksgiving even though airports set records for the amount of people passing through security checkpoints. In fact, the TSA set the all-time single day record when their officers screened over 2.9 million individuals the Sunday after turkey day.

However, if there’s a brutal storm, it could throw everything off so below are my best holiday travel tips, including information on booking tickets, getting the best deals, navigating the crowds and generally, having a smooth travel experience.

1. How to find cheap holiday flights
If you haven’t purchased your airplane tickets, what are you thinking? If you subscribe to my daily travel tip newsletter, then you know that I was advising people back in the summer to buy their tickets. The good news is that if you can be flexible with the dates/times, then you should be able to find a good deal. Here’s my advice to find cheap tickets and be sure to set a fare alert, even after you purchased your tickets.

These days, most airlines don’t charge change fees as long as you don’t buy Basic Economy tickets or fly ultra low-fare carriers (always read the fine print.) That way, you can cancel your flight and rebook if you find a cheaper flight (highly unlikely) or if someone in the family gets sick (highly likely) so if you need to cancel, at least you won’t lose the money. You just need to apply it to another ticket on the same airline within a year of purchase.

RELATED: Flight Delayed or Canceled? Here’s What You Need to Do

2. Use a travel agent
I made my career thanks to the internet but if you’re traveling over the holidays and don’t have top tier elite status on the airline you’re flying, then I would find a reputable travel agent and have them book your tickets (ask your friends who they use). That’s because if there’s a snowstorm, massive volcano eruption, an airline has an IT meltdown or a strike, then you don’t want to spend hours trying to get on the next available flight. It’s well worth spending $25-$50 per ticket to have a good travel agent do the dirty work if you-know-what hits the fan.

3. Give yourself extra, extra time
Speaking of getting on the next available flight … If you miss your flight because you woke up late, got stuck in traffic, your Uber didn’t show up or you couldn’t find airport parking, you need to realize you could be stuck for days and be on the hook for some major costs. It’s critical you give yourself enough time because if you miss your flight, good luck getting on the next flight because as I said above, flights are going out full. Leave extra early or be prepared to purchase new tickets.

4. Have a back-up plan
If you absolutely cannot afford to get stuck, then buy a refundable back-up ticket on another airline, connecting in a different region of the country (in case there’s bad weather) for a few hours after your original flight. That way, if your original flight gets cancelled or you get stuck in traffic, you aren’t totally screwed. Just make sure to cancel the flight you’re not taking before the cut-off time (usually before departure time). Here are some more tips about this nuclear travel hack.

5. Double check your reservations 
My family and I flew from Turks and Caicos to Los Angeles (via Miami) the Tuesday before Thanksgiving. The only hiccup was a rookie mistake I made. I did not double check all of my reservations as I normally do. And guess what? I had accidentally booked a car service for the following week. So we had to wait 25 minutes at LAX for an Uber Black, which felt like an eternity with two little ones who had been traveling for 12 hours. GOOD TO KNOW: If you are traveling to LAX, here are some important tips.

6. Book airport parking or your ride in advance 
As you probably learned from the tip above, it’s important to pre-book rides in advance. If you’re planning on parking at an airport, keep in mind that many lots are full over holidays. If you want to guarantee yourself a spot and save money, then pre-book parking.

7. Book nonstop and morning flights
This summer I wrote a tip titled, “Every Travel Expert’s Secret For Not Being Stuck in the Chaos.” I explained why I dragged my kids out of bed in the middle of the night to make an early morning flight. The reason why is because if there’s a hiccup like a mechanical problem or a crew member calling in sick, then just one flight can create a domino effect. Another reason is that bad weather usually happens later in the day so if you leave early, you have a 25% better chance of getting to where you want to go on-time.

8. Book longer layovers
Unfortunately, in the example above, I couldn’t book a nonstop flight from Naples, Italy to Toronto, Canada. That’s why I purposely booked a long layover. I could have had us take a much later flight but our layover in Munich, Germany would have only been an hour, which was way too risky. Instead, we made a day out of it to drastically lessen the chances of misconnecting, relieve the stress and get a taste of Germany (literally). Here’s the story.

9. Don’t check bags
If you ask any frequent flier their best travel tip, the majority will answer with, “Don’t check bags.” This way, you don’t have to show up to the airport extra early to check it, wait around for what seems like an eternity at the baggage carrousel upon arrival, worry about your bags getting lost or having items stolen. A carry-on bag will also save you money on baggage fees, allow you to take public transportation more easily and get on a different flight if your original one is delayed or canceled. However, not many people can travel without checking a bag. I’m one of them when I’m with my family. So if you are checking bags and you really want to know where your bags are, a good little trick a lot of frequent travelers use is to pop an Apple AirTag in their checked luggage. You can buy them at an Apple store or on Amazon for $27 for one or $80 for four (NOTE: that price is accurate at the time of this publication). For those with Android phones, you can use Samsung’s SmartTags.

10. Get travel insurance
I’ve worked with Allianz Global Assistance for almost a decade but even if I didn’t, I would still recommend buying travel insurance since it gives travelers great peace of mind. Just make sure you read your policy’s fine print and double check the coverage you get from your credit card company.

11. Pay with a credit card
Regardless of whether you’re buying a domestic one-way flight or an African safari package, always protect your purchases by using a credit card and not a debit card. With a credit card, you’re protected by the Fair Credit Billing Act. Per Cornell Law, “The Act requires creditors to give consumers 60 days to challenge certain disputed charges over $50 such as wrong amounts, inaccurate statements, undelivered or unacceptable goods, and transactions by unauthorized users.” With a debit card, you’re out of luck.

TIP: Always set up text notifications for purchases so you know exactly when your credit card has been charged.

12. Upgrade
If you haven’t purchased your ticket yet, then don’t just look at economy fares. Since there are not a lot of business travelers flying over the holidays, you can sometimes find much cheaper first-class fares. There are a lot of factors involved but always doublecheck and keep in mind that it could be cheaper or just a little bit more, especially when you factor in all the airline’s add-on fees like checked baggage, assigned seats, food/drink, etc. If you’ve already purchased your seats, then check to see if you can snag an upgrade for cheap.

13. How to get the best seat
If you can’t fly first class, then at least aim for getting the best seat in economy (usually the exit row or bulkhead). First, consult SeatGuru.com for the best seat on your type of aircraft, then sign up to ExpertFlyer so they can monitor your desired seats so you don’t have to keep checking yourself. You can choose a specific seat, like an exit row aisle or a type like any window or aisle. When one opens up, you will be notified. Seats can open up anytime but typically start five days to 24 hours before departure and lasts all the way up to boarding. This is when airlines start upgrading their frequent fliers who almost always have the best economy seats already reserved. So, when they get lucky, you can too (if you’re quick).

RELATED: If An Airline Severely Delays or Cancels Your Flight, Are They Obligated to Cover Your Hotel Accommodations?

14. Be extra nice
If you’re a regular reader, then you know that my number one travel tip is to always be genuinely nice to everyone but especially to gate agents and flight attendants since they most likely don’t want to be working over the holidays. They would much rather be home with their families than listen to you whine. As you know, agents and flight attendants already had a difficult job pre-pandemic and now they’ve been putting up with a whole lot of crazy post-pandemic. I always make sure to greet them with a smile and almost always bring them a box or bag of chocolates.

I hope these travel tips help you travel as safely and smoothly as possible this holiday season. If you find them helpful please share with your loved ones and sign up to my free newsletter.

KEEP READING

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• 10 Airport Security Hacks Every Traveler Should Know
• How to Get the Best Coach Seat on the Plane
• The Sleep Hack Every Traveler Needs to Know
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