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Learn From Me: The 7 Dumbest Travel Mistakes I’ve Made

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It's easy to make costly mistakes when booking travel. I've made too many of them myself, and I'm supposed to be a pro at this…

Whether it's botching the international birthday format, having autofill ruin my name on a reservation, or waiting too long to book flights and having it cost me hundreds of dollars, there has been no shortage of mishaps and failures in my travels. 

At Thrifty Traveler, we're all about giving people the basics and knowledge to become smarter travelers – and avoid costly mistakes. That's why we cover everything from the basics of how to find cheap flights, using Google Flights, and the best day to book flights all the way up to how to use points and miles to fly to Hawaii, Europe, or Japan – and the biggest mistakes travelers make using their points.

There are members of our Thrifty Traveler team who have flown first and business class cabins across every ocean using points and miles … and some of us are just getting started on our journey of learning how to travel more for less. The common thread between us is that we're all still learning, and often, we're learning the hard way. 

So, I thought I'd confess seven of the biggest travel mistakes I've made over the years and cop to those fumbles and foibles so you can do better than I did.

Please withhold judgment as I lay my travel sins bare in this travel confessional.


Overpaying for Flights

As a flight deal expert finding fares to send to our Thrifty Traveler Premium members, I love seeing our subscribers book dirt-cheap flights to their favorite destinations around the country – and across the globe. But it's also painful: I've realized how much I've overpaid to fly to some of these destinations in the past.

Here's an example: Fresh out of college, I booked a trip in February 2016 to the Swiss Alps, flying from Minneapolis-St. Paul (MSP) to Zurich (ZRH). I paid about $800 for a roundtrip economy fare. Now, every time I find fares like these, I kick myself for not saving all that money at a time in my life when money was so tight. 




Knowing I could have booked nearly the same flights from my home airport for under $500 was rough – I could have bought two tickets for about what I paid back in 2016. Worse yet, just days before we found that first Swiss deal, we clued Thrifty Traveler Premium members in on a way to fly to SWISS business class for just 60,000 each way. 




Had I been a subscriber back in 2016, this all could have been at my fingertips – and my lean, post-grad bank account would have thanked me. I guess I didn't know how bad of a deal I was getting when I booked it initially…so ignorance is bliss, but now my veil has been lifted and I know I got fleeced. Never again. 


The Birthday Issue

Some mistakes you learn from, and some mistakes get you over and over again. When it comes to checking my birthday on my bookings, I refuse to learn, and it's come back to haunt me a few times over the years. 

The first time it happened to me was in the lowest-stakes scenario possible. I was flying domestically, from Florida to Minnesota, and fat-fingered my date of birth on a budget airline's website and got it wrong by one day. On the way down to Florida, I was waved right through – nobody noticed a thing and I took my flight no problem. But on the way back, a discerning TSA agent noticed my birthday was wrong on my reservation compared to my ID and I was turned away. I had to go stand in the check-in line (behind about 75 members of a college baseball team who were all checking three bags each onto the flight) and wait about an hour and a half to fix my birthday, re-check-in, go through security, and just sprint onto my flight before the boarding door. 

“Never again,” I told myself…just about four months before it happened again. 


PLAY Airlines check-in desk


Soon after, I booked the inaugural flight from the U.S. on PLAY Airlines up to Iceland (KEF) from Baltimore (BWI). The ultra-low cost carrier had never flown from the U.S. before, and its website was a little janky. I selected my date of birth, double checked I had it right, and booked without a hitch. About two weeks before travel, I triple-checked my date of birth, only to see that it was one day earlier…what? 

I tried to fix it online – no dice. I called my sister who I was traveling with who also had her date of birth changed by one day as well. Weird. I called PLAY and they told me it was an issue with the new U.S. flight where all of the dates of birth were affected by one day because the airline didn't account for the time difference between the U.S. and Iceland. (I also don't know how this is possible, but whatever.) So at the airport, everyone on this flight had to check-in in person to resolve the birthday issue, causing a long delay and a painful day at the airport. 

That one wasn't my fault, but these last two definitely were. 

When you fly with international airlines, they often do dates and birthdates the opposite way we do them. In the U.S., we do Month/Day/Year. Internationally, however, they often do Day/Month/Year. So my birthday of 04/01/1993 in the U.S. should be 01/04/1993 in most other countries…including on their airlines. 


Date of Birth
Entering your date of birth on Lufthansa. A helpful format reminder appears underneath. Lesser travelers may ignore that reminder, though…


My birthday on my Avianca LifeMiles account (which I used to book TAP Air Portugal, SWISS Business Class, and SWISS Economy fares over the years) was wrong on each and every itinerary I had, requiring me to make frantic phone calls to customer service to remedy the issue over and over again. The same thing happened on my Qatar Avios account, which took months for me to remedy after repeated calls and emails to their customer service as well. It kept me from linking my British Airways and Qatar Avios accounts, which made me miss out on some amazing flight deals along the way. 


Birth date Qatar


Luckily, many of these airlines know that this is a pain point for some flyers and have spelled things out really simply (like Qatar did above) for bone-heads like me. Just double check and triple check your birth date on your itineraries so you don't learn the hard way (five-ish times). 


Breaking the Flight First Rule

When it comes to planning travel, this is a mistake we see all too often. It could easily cost you hundreds of dollars that could be used on making your trip better. And I've made it, too.

In the past, I'd choose a destination and decide on my travel dates, then request time off from work. That's when I started looking for flights … with my dates locked in and my options therefore limited.

At Thrifty Traveler, we have a rule. It's called the Flight First Rule.


Best Flight Deals 2018


Instead of deciding on the dates of your trip before booking your flights, start by searching for flights, letting the price guide you to the cheapest dates possible. Flexibility is crucial if you want to save on flights – and trust us, it makes a big difference.

You might be shocked at how much you can save just by departing a day earlier or later than you initially planned. By traveling during cheaper seasons, you could save even more.

I used to book travel around pre-determined dates or destinations – and paid $800 to fly to Switzerland as a result. Now I let cheap flights and deals lead the way.

Can’t be flexible? Travel dates set in stone? Set a Google Flights Price Alert to get notified when the price of the flights you need drop!

When I get a Thrifty Traveler Premium alert in my inbox, I book the fare at its lowest price and start building a trip around that cheap fare. Part of the reason I can confidently do that is the 24-hour free cancellation policy guaranteed for nearly all flights to, from, or within the U.S. That's a 24-hour window to determine whether those dates will work – and if I can get time off.

I know this story is about my travel woes, but allow me to brag for one minute by illustrating a (rare) instance where I did things right!

When my colleagues and I at Thrifty Traveler Premium put out this sizzling deal to Havana, Cuba (HAV), I immediately followed the link to book it directly with the airline. I booked two tickets from Minneapolis-St. Paul (MSP) to Havana (HAV) for $354 each.


Cuba flight deal


As soon as I booked it, I called my wife and asked her if she could make the trip work. She gave me an emphatic thumbs up. Then, I emailed my boss to ask for the time off. Approved.

And just like that, we had an April trip to Cuba on the books! Cuba wasn't a place we had high on our list and wasn't something we were locked into doing in mid-April. Instead, we planned a dream trip based on the cheapest flights possible. 

Flights are almost always the most expensive part of any trip, so making sure you do the best you can on that expense should always be your priority when booking travel.


Being Too Slow to Book Flights

When you see a good fare, book it! Handle the rest later. Utilize that 24-hour free cancellation window to handle the logistics and decide if your decision was too impulsive.

My list of mistakes on this front is too long to recount. Far too often, I've dragged my feet on booking a cheap flight, only to return to it later and found it's increased by $100 or more.

The latest example really killed me. I wanted to fly from Minneapolis (MSP) to Louisville (SDF) for the PGA Championship golf tournament in May. I was about three weeks out from the trip and the nonstop Delta flights were around $389 one-way…ouch. But, if you booked the same flight through Air France/KLM Flying Blue, it was just 7,500 miles. It was a screaming deal to save almost $400. I called my travel companions to make sure the trip was a go, promising myself I'd book first thing in the morning. 

Poof. Gone. Vanished. In just a few hours, the award availability slipped away and I was stuck with only expensive options. The 7,500-point rate slipped through my fingers and cost me hundreds. I could have booked with the 24-hour rule protecting me and snagged a nearly free flight to the PGA. 

The 24-hour change-your-mind rule is possibly the most helpful budget travel tool there is. If you see something great in the airfare space, it's not likely to last. Book it! Then start asking the big questions about your travel companions, your time off requests, and who is going to watch the kids and dogs. So long as you can come up with answers within 24 hours, you're in the clear.

Another tactic I wish I had used more as a nascent traveler is capitalizing on fare differences. That's right: On major U.S. carriers like American and Delta, when the price of your previously booked flight drops, you can change your reservation online and get an e-credit for the difference in the fare. 

Read next: As Flight Prices Drop, Rebook Your Flights & Save Even More!

Say you booked two main cabin economy, roundtrip tickets for a vacation to Lake Tahoe (RNO) for $300 each. As soon as you're done booking, record your flight price somewhere, and then go find your flights on Google Flights and setup a Google Flights Price Alert. If and when that price goes down, Google will send you an email alerting you to the price change. Then, all you have to do is go change your flight if you're flying American or Delta, or cancel and re-book your flight at the lower rate if you're flying another airline.

There's also no better example of the need to act fast than when a mistake fare crops up. Just a few weeks ago, we found this ridiculous mistake fare to Dublin (DUB) from Minneapolis (MSP) and Chicago (ORD). 


Mistake fare dublin


The second you see a mistake fare or a unicorn deal like this, drop everything and book it. Ask your boss for time off after your tickets are booked. Book a ticket for your favorite travel companion rather than try to align schedules first – the fares could easily disappear before you get a response.

That's exactly what Thrifty Traveler Marketing Manager Amber did when this deal hit her inbox. She booked first, and then texted her husband to see whether they could make the trip work. She had 24 hours to get a yes or no from her husband and her time off approved. Easy-peasy. 

Read more: All About Mistake Fares, and How to Find & Book Them


Being Too Loyal to Airlines and Hotels

Your loyalty to one particular airline or hotel chain is costing you money, plain and simple. I know it cost me plenty over the years.

Sure, we've all got our go-to airlines that we prefer over competitors. But strict hotel or airline monogamy means those brands are beating you at their game. Airlines and hotel brands are making millions of dollars from customer loyalty.

Over the past few years, thanks to co-branded credit cards that make it easier for more and more travelers to get and keep status, status is getting less valuable. More and more people fight for the same complimentary upgrades, making whatever status you managed to earn inherently less valuable.

As a Minneapolis resident, Delta loyalty is tempting. They have a great onboard experience and tons and tons of nonstop flights to some of my favorite destinations. I'm guilty of paying much more to fly Delta, even when Alaska, American, or United are offering lower fares. All in the name of chasing status…

If you really want to travel more for less, flying on the lowest fares from a handful of different airlines and saving hundreds in the process, all while earning miles on a handful of different airlines is the way to go. And that's the right course of action for almost every average traveler out there, myself included. 

I do the same thing for hotels and rental cars now, too. Instead of continually throwing money at just Hertz or Marriott, where status can be hard to earn and isn't that valuable, I cast a wide net and get myself the best rates instead.

Brand loyalty doesn't pay, especially because that brand ultimately doesn't care a wink about you. 


The Last Name Saga

At the Thrifty Traveler office, my colleagues jokingly call me “Gunnar Olson Olson Olson” because of this ridiculous mistake that took literally years to resolve. 

When I entered my information into my Avianca LifeMiles account for the first time (besides getting my birthday wrong as I already noted above), I also let the autofill feature on my web browser put in some of my information to save time. Unfortunately, the autofill put my last name into the middle name bar…and the last name bar. So my name on my account was “Gunnar Olson Olson.” 

When I called the Colombian airline, they told me it “probably wouldn't be an issue” for my honeymoon flights I had booked nearly a year earlier. Given that my itinerary left Nairobi International Airport (NBO) at 4 a.m., I decided I didn't want to risk miscommunication with a desk agent, and I called Avianca to make the change. They told me it was not possible and that I would have to rebook the flights – which is always risky when using points and miles because the award space isn't always there. 

I called one last time to see if I could find an agent who could help me out of the goodness of their heart – and I did! I told them my last name was listed as Olson Olson and it should just be one Olson. Well, one more miscommunication led to them adding an “Olson” to my last name instead of subtracting it from my middle name. Hence, Gunnar Olson Olson Olson was born. 

In the end, I had to rebook the tickets to fix the issue. Luckily the award space was still there and we were able to cancel and re-snag the same seats over again…with just one Olson this time. 

Double check your personal information and take it slow when booking. My harried booking caused me hours of problems afterward. 


Swiping the Same Old Credit Card

This is my biggest travel mistake, and for the longest time I didn't understand why. When I did the math, I realized I was leaving valuable points on the table, even if I was earning a few miles with every credit card swipe.

For years, I swiped my *delta skymiles gold card* every chance I got, telling myself earning SkyMiles to fly on my favorite airline was the wise move. During that time, I earned just one credit card welcome bonus, earning just a few hundred extra SkyMiles each year for my everyday and travel spending.

The points earning was slow, giving me 1 SkyMile for each buck I spent. And when it came time to use them, I was handcuffed to just Delta SkyMiles.


book flights with credit card points


Now, I have a few different credit cards that earn flexible points like Chase Ultimate Rewards, Capital One Venture Miles, and American Express Membership Rewards – points that I can transfer to a few dozen different airlines and hotel chains. Plus, I've earned more than 200,000 points in welcome bonuses in a matter of months – much more than I would have earned if I just kept swiping my Delta card. 

With my *venture x*, I also get 2x points on all purchases and a $300 travel credit per year, which really takes the thinking out of the equation and gives me a “swipe anywhere” kind of card in my wallet. 

Critically, I've gotten over my fear of annual fees with credit cards. Whether it's $95 or $695 a year, it's a big roadblock for many travelers. But I realized that with the amount I spend on travel each year, even costly travel credit cards are saving me money – especially hotel credits, airline fee credits, and more.

Just so we're clear, credit cards are serious business. It's important to go slow and never spend more than you can afford to pay off in full, each and every month. No matter how many points and miles I've earned, staying debt-free is far more important.

Branching out beyond earning and burning SkyMiles changed everything for me. Now I fly some of the best airlines in the world for next to nothing and the points reappear in my account faster than ever – without spending any more money. 


Bottom Line

If you'll forgive my travel sins, hopefully, you can learn from them as I did.

Was there pain along the way? Absolutely. Is there sleep-depriving regret? For sure. So please learn from my mistakes so you don't make them, too.

Editorial Disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airlines or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.

Disclaimer: The responses below are not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved or otherwise endorsed by the bank advertiser. It is not the bank advertiser’s responsibility to ensure all posts and/or questions are answered.

1 Responses

  • I get the not being totally loyal thing. And I too am a Minnesota based traveler. But as a premium guy on Delta, Marriott and Hilton, I get way more in return, especially when things go south. With 3500 plus flights, I have had more than a few that required help.

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