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We’re giving away another Southwest gift card (thanks to the ever generous, long-time reader Caveman), but this time the conditions of the giveaway are going to be a little different.

While most of you reading this blog probably consider yourself travel experts, at least to a degree, that doesn’t mean we haven’t made embarrassing mistakes. We’re all human here. There’s nothing more endearing, and humanizing, than stories of ourselves being idiots. We want to hear yours!

Tell us your cringiest screw-ups and embarrassing moments traveling. I’ll pick two that I find to be the most entertaining and publish them on the blog. I’ll leave it up to you guys to vote for the winner in the comments. The reader with the most votes will win a $101 gift card from Southwest that never expires (with quick and easy delivery through email).

Steps to Win

  1. Send your travel goof (keep it to one, please!) to or leave it as a comment on this post.
  2. Wait for my follow up post with my top two choices.
  3. Vote in the comments of the follow up post with your top choice (aside from your own, let’s actually make this fun people!)

Our Travel Goofs

Scott’s (by Scott)

One time I flew to Las Vegas for a World Series of Poker tournament, with a plan to fly to Phoenix afterwards to be interviewed on the television show “The List”.

I had bought the perfect string of awards, Honolulu > Las Vegas > Phoenix > Honolulu all with Avios. Sitting at the poker table, with my flight in a few hours, I decided to re-check my reservation and noticed that I didn’t in fact book Las Vegas to Phoenix, I booked it backwards, Phoenix to Las Vegas.

I called British Airways and explained the situation, but they told me that since it was within 24 hours of departure, there was nothing they could do. They couldn’t cancel and redeposit my miles. So I had to go online and book myself another award for 4,500 Avios + $5.60 from Las Vegas to Phoenix that left a few hours later.

Sarah Page’s

It’s your lucky day! You’re getting two goofs for the price of one from me. Also, mine are way better (worse?) than Scott’s. Unfortunately for me.


The first happened when I was backpacking in Brazil a few years ago. I was in Florianópolis, out drinking and saying goodbye to new friends I had met as I was scheduled to fly to Salvador the following day. It was a long night that concluded in watching the sunrise from the top of a very tall sand dune. A great way to go out–or so I thought.

I arrived at the airport the following afternoon in time for my flight at 3 PM. Except there was no flight at 3 PM.

The GOL attendant kindly told me that I must be mistaking what was in fact a 3 am departure for a 3 PM departure. Oops.

In what seemed like Karmic punishment, I sat hunched in a hungover and angry stupor, considerably poorer after buying a last minute flight, waiting for hours to leave on a later plane that evening.


Ironically enough, I had quite an embarrassing travel experience just this morning.

I left for the Atlanta airport with what I thought was plenty of time. My estimate was naive, I suppose, albeit not totally my fault as there was a wreck. I sat in traffic–I know, go figure, it’s Atlanta–and arrived to Harts-field-Jackson much later than anticipated. The attendant at the Alaska counter told me check-in was closed and that I’d need to reschedule. My face dropped and I asked her if there was ANYTHING I could do aside from calling reservations, promising her I wouldn’t hold them accountable if I got to the gate to find out I had missed the flight. She reluctantly agreed, but told me there was nothing she could do about the bag I needed to check, it was too late for that. I’d have to haul it through the airport and try my luck gate checking it.

Then I ran, faster than I ever have through an airport, with one carry-on size roller, one larger check roll bag, and a backpack on my back. Not exactly the best time to be traveling weighed down, but it was my only chance.

I bustled through security as “that person”, sweaty and anxious, asking everyone if I could move ahead of them in the centuries long line. So many people gave me looks and eyebrows at my obviously oversize luggage, and a few even asked if I thought I was going to board the plane with all that stuff. But the majority of people were helpful and nice, encouraging me to push past them, and security even let me through with some liquids they shouldn’t have after scanning them separately.

I arrived at the gate in a full on sprint and….

View from the wing, no pun intended, on the decent into Portland
View from the wing, no pun intended, of Mt. Rainier on the decent into Portland (ATL > PDX)

….made the flight.

At least that goof has a happier ending than my last. Looks like I’m getting a little better at this with age.

Bottom Line

Ever showed up for a flight that wasn’t actually booked? Had your pants sucked in and pulled down by an escalator? The second is a true story, thank goodness one belonging to my friend and not me… 😉

Share your biggest travel goof with us for a chance to win a $101 Southwest gift card! Keep an eye out for a follow up to this post with the top two stories, and remember to vote for a winner in the comments.

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