Travel isn’t always perfect and we certainly aren’t either. This week on the show, Gunnar and Kyle cop to the worst travel mistakes they’ve made over the year.
From rehashing Gunnar’s Avianca last name fiasco to entering birthdates wrong to over-scheduling trips, getting fleeced at an expensive restaurant, and even timing bathroom breaks on the road, the guys have screwed up a lot over the years. Join us as we discredit, debase, and humiliate ourselves!
Tune in now on YouTube, Apple Podcasts, Spotify, or wherever you get your podcasts! And be sure to subscribe now to get each new episode every Thursday morning (plus the occasional Tuesday bonus episode!)
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Show Notes
00:00 – What’s the biggest mistake travelers make?
02:50 – Sylvia welcomes us to the show from Zion National Park
05:15 – The Gunnar Olson Olson Olson story
07:10 – Not checking airfare from more than one airport
09:20 – Think before you swipe: Using the wrong card to book flights
11:55 – Over-scheduling travel – Kyle’s slightly-too-much trip
14:00 – Not paying attention to open hours
16:15 – Birthday fiascos and infant reservations: Don’t wait until the airport!
19:40 – Getting a ski trip shuttered by the weather
22:30 – A word from our sponsor: Don’t miss the next great flight deals with Thrifty Traveler Premium
24:20 – Letting e-credits expire
26:15 – Leaving something in the overhead bin
28:30 – Swiping the same old credit card
30:40 – Check the menu: A crazy expensive meal in Singapore
32:35 – The pre-boarding bathroom break
34:40 – A listener asks: Why the “Yo?”
36:12 – Another listener asks: More on our rebooking strategy
43:05 – The biggest mistake Gunnar has made at Thrifty Traveler
Produced and edited by Sylvia Thomas
Video editing by Kyle Thomas
Show music: “All That” by Benjamin Tissot
While listening to your “biggest travel mistakes” podcast, I had a sudden flashback to my own international disaster.
A few years ago—back when I was dating my now‑husband—we booked what we thought was the deal of a lifetime: a trip to Jamaica through VacationExpress. Flight and resort for $800 per person. We were thrilled. Financially savvy. Basically travel influencers in our own minds.
Cut to us landing in Jamaica, sipping mimosas, feeling elite… until immigration.
I hand over my passport and—surprise—it turns out a page was missing. This was 2015, when passports were apparently held together with the world’s weakest staples. Between trips to Machu Picchu, South Africa, and several Caribbean islands, a page had quietly escaped.
And I should mention: I did not know passport pages were numbered. That’s how unprepared I was for international travel.
They pulled us aside into an immigration office with some truly sketchy characters, then calmly escorted us… back onto the plane we came in on. Didn’t matter that we flew from Cincinnati—the plane was now headed to Nashville, and that was that.
I was a wreck. Full panic. The flight attendants felt so bad they upgraded us to first class, which I absolutely did not emotionally deserve. I vaguely remember drinking several glasses of wine and staring into the void.
Technically, my boyfriend could’ve gone into Jamaica while I flew to an emergency passport office, but instead we accepted the loss and re‑routed ourselves to visit my future sister‑in‑law in northern Utah. In early fall. In Jamaica clothes. But hey—we still had fun. Just cold. Very cold.
So PSA for everyone listening: treat your passport like the sacred document it is. One ripped or missing page can end your vacation instantly.
And yes—the question everyone asks: “Did you get your money back?”
We did not. My now‑husband hates travel insurance, so goodbye $1,600… plus extra airfare to and from Utah. Would insurance have covered it? No idea. I didn’t even try. (Now that we are married we always get insurance or make sure a travel credit card has it!)
And just when you think the story’s over—years later, with my brand‑new replacement passport, we crossed into Canada on foot at Niagara Falls right after Covid restrictions eased. On the way back into the U.S., the agent says, “You know your passport isn’t signed, right?”
MORTIFYING.
They let me sign it and sent me on my way, but honestly? I think it’s fair to say I should maybe not be trusted to leave the country.
I enjoyed the episode, but I have to call you out, Kyle, on the Borough Market story. Your distance estimates felt off, so I checked . According to Google Maps, it is a 1.8 mile walk from Trafalgar Square to Borough Market, not the 7-10 miles you mentioned in the episode. Also, London has busses – and the front row of the upper deck on one of those double decker busses is one of the most fun ways to ride around the city. Were they on strike too?
Gunnar, Really disappointed to see You use the three letter abbreviation for such an offensive word in the title of this podcast. I’m sure you could have found a more respectful way to ask the question what is happening with flight prices. I hope you consider keeping things clean in the future.
Tell Kyle no one cares he is a straight white male and continually bringing it up is offensive. If he was a blind blonde lesbian african american pacific islander no one would care. Grow up people tune in to get the information and couldn’t care less about someone’s gender and ethnic make up.
I was just poking fun at myself/trying to show some self-awareness about the privilege of complaining about flying business class … but yeah, probably dropped that line one or two too many times.
Hey! Don’t knock the Hyatt Place Northwest/Medical Center. It is the closest and most convenient Hyatt for visiting Six Flags Fiesta Texas! 😉
*As a Globalist*…
But really, as a Globalist who travels with two kids and basically only ever uses points (other than Platinum credits for THC) I do think there are aspects that can’t really be replicated elsewhere unless you’re independently wealthy. As Gunnar pointed out the footprint is a challenge and may prevent me from requalifying this year, but there’s just so much that being a Globalist allows me to do that wouldn’t be possible without it unless I drained all of my Amex MRs at 1c each to book via FHR/THC. The combination of milestone rewards and straight Globalist benefits is second to none for a family – I can use 25k points per night (or less) and a suite upgrade award to put our whole family into a great room at a nice hotel with free breakfast and parking. And sometimes I can throw a Guest of Honor award at my extended family so that the cousins can come too! We just wouldn’t be able to travel as much or as well as we do – and with the people we love – with the other disloyal hotel options you mentioned*.
*The Edit with a Points Boost might be the next best thing for our needs but I’ve lost count of my rejections from the CSR personal card.