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Tales of Juicy Travel Disasters — And How to Overcome Them

Stefan Loble

Stefan at a pay phone in Cuba.


When we travel, it’s pretty darn common for things to go wrong. This is no surprise, given the relationship between how exciting a destination is, and the complexity or even risk that goes along with experiencing it.

A trip sometimes feels more like a mission — I need to do this, that, and the other thing within a certain time frame, and without getting ripped off. As a result, I’ve noticed that when problems arise overseas, it can feel like my entire life is hanging in the balance and our emotions can be inflated.

For a little perspective, here’s a rundown of some things that go bad while traveling, and how each situation turned out in the end.

Carry them with you, and maybe you’ll find a little comfort the next time you’re in a jam, and see that maybe things aren’t as disastrous as they seem...

Transportation Disasters

The entry point to all travel go-wrongs is transportation. And sooner or later, a dramatic missed connection is going to happen.

One of our customers got stuck in Narita airport in Tokyo after a bad snowstorm shut down the city… for three days.

“All flights were cancelled and so I (along with thousands of other people) was stuck in the terminal with nowhere to go. So I slept in the terminal for about 23 hours with all my work gear and personal stuff. Finally JAL managed to book me another flight but from a different airport on the other side of Tokyo. So I had to take the train all the way across a strange city I'd never been to with all my stuff. I finally managed to get to Okinawa — three days late without a shower in disgusting clothes.” — Luke Koetje

In the moment when we’re trying to get somewhere, our mission seems like the most important thing in the world.

When this happens, I like to consider how bad the situation is in terms of what’s really at stake. Am I in danger, or merely just delayed? After all, travel is a luxury to begin with, and many of the places we visit are so interesting because they’re remote and less developed, making missed connections the norm.

My best weapon for being delayed in the airport is entertainment. I like to keep it fun, make new friends, and help people — like stranded families — to feel better about my experience.

Maximum potential impact: Medium. You could lose time and a stack of money, which will sting in the moment, but life will go on.

Embarrassment and Rookie Mistakes

The second dynamic built into travel is feeling like a fish out of water. Different cultures, languages, and complex logistics often can often make the simple seem daunting. As a result, travel can be filled with small embarrassments.

Our copywriter Lacy had her own special recipe for embarrassment. Instead of one of those small, private moments far from home that few people witness, Lacy decided to present herself publicly to lots of people of her own culture, that she was also destined to spend a lot of time with.

We realized something was wrong almost as soon as we arrived at the eerily empty cruise terminal. We spotted the ship at the far end of the terminal (easily half a mile away or more), and when it blew those enormously loud horns, we started to run.

We didn’t know that ‘all aboard’ is not the time you begin boarding the ship, but rather the time you must be aboard.

We managed to make it to the embarkation point just before they pulled up the ramps. Once on board, the Purser took us to register. ‘It’s OK,’ he consoled me, sensing my all-too-public shame, in front of hundreds of my fellow cruise ship passengers lined up along the decks…. ‘You made it, and that’s what counts.” — Lacy Boggs

I enjoy this story most when I imagine Lacy running (sorry, Lacy) inelegantly, down a huge empty port under blazing sunshine. As she runs, I see a few plastic shopping bags banging together, maybe a few tacky souvenirs, even a goofy hat falling off her head. There she is, all mad at her husband like Damnit, I told you not to buy the pinata.

And that’s the thing. Objectively it wasn’t a huge deal — although being stuck at port would have been bad. Instead, the moment of embarrassment is the worst for whoever is on the receiving end.

Therefore, while I’m always looking to travel smoothly  experienced, aware, and trying to appear familiar with the unfamiliar  when I goof up, I’m going to laugh about it.

Maximum potential impact: Low. You might have a red face, but it’s not going to affect your life long term. Embrace the story.


In some parts of the world, theft is par for the course. When our designer Akemi spent a year in Accra, she quickly learned that theft was part of the cost of living.

“I always carried the equivalent of $5 and my crappy flip phone on my person — never my passport or any credit cards. At one of the games of the Africa Cup of Nations soccer tournament, everyone was pressed up against each other trying to get in, and I felt a man’s hand slide into my pocket (not elegantly — it was actually sadly funny to me how obvious he was). My hand was wrapped around my phone as a precaution, and so there followed a goofy tug of war where I pulled and he pulled. I finally just let it go. After you get mugged a few times, you realize how unimportant your physical stuff really is.” — Akemi Hiatt

Here’s the deal — I suggest not getting angry about theft. I know stealing is supposed to be universally wrong, but it isn’t about you personally. Any visitor with resources is a target.

When I’ve had something significant taken, as I peeled back the layers — imagining the person who took it, thinking about how different our lives were leading up to this moment, and how different they were going to be going forward — there were few simple answers that made me feel better about “right and wrong.”

My suggestion is to defend against big losses than will ruin your trip. For example, I use the hidden pockets in our pants and travel blazer to split up valuables, and make them generally far from reach — to combat prying hands.

Maximum potential impact: Medium. It can definitely suck if a significant amount of money or your passport is taken. But, there are ways to reduce the impact. In particularly rough destinations, I suggest splitting your valuables and preparing to give up something small, should real force be used.

Health Disasters

Both at home or abroad, we’ve all been there… where our body isn’t on an even keel.

Once, when I was a young lad in Calcutta, India, I drank a liter of water straight from the tap. Late at night, it was a last resort. I’ll spare you the details, but suffice it to say the impact was dramatic and notable… striking a day later on public transportation.

I have observed that the consensus of most experienced travellers I meet is that dangerous places for food safety aren’t what many fear — the market stand is not as much of a threat as a mid-range hotel.

The bargain I struck with my wife is that whatever embarrassing thing happens overseas, has to be confessed so others can laugh. This is in preparation for when it’s their turn.

Maximum potential impact: Medium. For most people the impact will be some discomfort and an inconvenience. Of course, more serious things can happen, particularly when we’re talking more about real safety versus comfort. The trick is to stay healthy enough to enjoy your trip.


It can be hard to know when you’re in real danger while you’re traveling — especially if you’re in a totally new situation, female, traveling alone, or all of the above. Laura Lynch of Savored Journeys learned the hard way that winging it with travel plans isn’t always easy on the nerves.

“I couldn’t find any information online about how to get from Montenegro to Croatia, so I decided to wing it. When I landed in Montenegro, there were no signs in English or even any taxis, just one empty shuttle bus. I explained to the driver that I needed to get to Croatia. He made a phone call and when he hung up, he barked at me to get on the bus and we drove off. This was step one, and after three more different men, a bus, a ferry, another drive and an unexplained transfer to a third car on the side of the road, began to panic. Being a women alone in these situations is extremely uncomfortable and I was sure I was headed for my death. Until micraciously, a sign for the Croatian border appeared.

Just one step left.... I needed to pretend to be the driver’s cousin, he explained to me in perfect English. And across we went.

Apparently, this taxi company had devised a way to get visitors into Croatia, though it wasn’t technically allowed. — Laura Lynch

I like this story because it shows how our ability to digest information from another culture, language, etc. can be so far off. I’ve experienced this a bunch of times, where I thought my hosts were bad guys, and they turned out to be sweethearts. On the other hand, a few of the times alarm bells told me to run, I’m glad I did.

Maximum potential impact: High. I have my own risk-benefit analysis. I often think about the statistics of riding in a car 1,000 times: scary moments are much more common than accidents, and minor accidents are much more common than bad accidents. In other words, the extremes are rare, but the potential for damage in those extremes is high. Family and kids have certainly altered my equation. I use the above to consider how bad a situations’ potential is, accept the possibility for minor disaster as a trade for a travel experience, and stay away from the more major perils...most of the time.

Emotion Overpowers Everything

Sometimes it’s hard to connect with your trip when something else is wrong. Our partnership expert, Katherine Conaway, experienced this first hand when she unexpectedly got dumped, and  a romantic trip for two to Morocco became a trip for one.

“After a rollercoaster eight-day trip, where I nursed my wounds, was harassed on the street, and woken by night terrors, on my way to fly out at 2am, my taxi got hit by another car on the highway. After I finally convinced the driver to continue and we got to the airport, I couldn't pay him because I didn't have any cash left and his app wasn't working to charge my card. I entered in the wrong terminal and had to run to the correct one — and with only 30 minutes to spare, the agent made the call. I was going to miss my flight.

And that is when I lost it.

As the unimpressed Lufthansa agent worked on rebooking me, I decided to attempt to explain myself, and managed to utter the phrase about being dumped . There’s a shift, and all of the sudden, she was full of empathy. The agent and a mystery man immediately helped me behind the counter to sit down in an extra chair. They offered me their condolences. The man even offered to let me stay at his family’s home. The upside was that a local friend hosted me at her home in Casablanca, and those two days with her family ended up being the best thing for my broken heart.

I was impressed by how Katherine’s travel disasters could have been a story on their own, but were diminished by her internal experience. Anything other than a worst-of-the-worst disaster, is not nearly as powerful as what we’re feeling inside.

If Katherine’s emotions can make travel bumps seem minor, then a more positive perspective — or a mindset of gratitude — should theoretically also be able to make travel problems seem small.

That’s what I try to do: “Yup, I’m delayed, but I am not injured.” You get the idea.

Maximum impact potentialMinor long term impact, but overwhelming power in the short term.

I suggest a three-part approach to taking on anything difficult on the road:

  • First, budget for things to go wrong when you travel to address logistical problems.
  • Second, look at things though the perspective of your overall life, not this one trip.
  • And third, if an emotion or event overpowers everything from left-field, then just go with it. If you are in Bali and don’t want to leave the resort, then don’t leave the resort.

If you have a story of a travel disaster that turned out OK in the end, I’m always all ears for a good tale. Who knows, maybe one of yours will provide me comfort, when things aren’t going so well on the road…

Stefan Loble



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