Nearly every seasoned traveler will have a slew of stories to tell about thier travel fails, mishaps, and embarrasing moments. It’s part of the experience, and generally something that can’t be avoided.
Whether that’s a missed flight, a broken down bus, or an excruciatingly long Uber ride (true story), things are not always going to go as planned.
Over time, we learn to navigate these travel fails and mishaps with ease, while hopefully preventing them from ruining an otherwise wonderful trip.
With experience comes the ability to find the humor in one’s travel fails. Well, most of the time anyway.
Just for fun, I thought you might like to read about some of the many things that have gone wrong for me while on the road.
I hope you enjoy these stories of travel fails and embarrassing moments, courtesy of my own inexperience, poor planning, and a dose of bad luck.
My top travel fails and embarrassing moments
That time I fell in Reykjavik (2019)
More of an embarrassing moment than anything else, I was enjoying some time walking around downtown Reykjavik one evening.
I had most of the major tourist hot spots to myself since it was both late and cold.
I found myself alone at the waterfront looking up at the Sun Voyager sculpture with the light from the Imagine Peace Tower in the background. It was peacefully quiet. The kind of quiet that falls over a city after a fresh snowfall.
I made my way over to the sculpture to get a better look. As I walked around to the far side, the ice got the better of me. Yup, that’s right. I fell on my a$$.
As I fell, I heard a faint gasp in the background. Sure enough, I look over and a small crowd had gathered. Just my luck.
I waved. They waved back. Whrere did these poeple come from? So much for being alone.
I stood up, dusted the snow off my rear, and continued taking pictures.
Nothing to see here folks.
That time I crashed my bike into the bushes while looking for alpacas (2019)
I was nearing the end of my trip to Copenhagen and was looking for a few more unique things to see before I had to leave.
I saw on social media that someone had posted pictures of a herd of alpacas in a park near my hotel. Of course I decided then and there that I needed to find these alpacas.
What I didn’t know is that the alpacas were not confined to a specific area of park. Instead, they roamed the area freely and could be anywhere at any time.
While I’m sure many of the locals know where to find them, this tourist did not.
As a result of my committment to finding these fluffy, long-necked cuties, I peddled my bike through the park. I made my way along muddy rain soaked trails, for the better part of two hours. Not one in sight.
During one particularly steep section of trail, I decided to allow gravity to do its thing. I peddled as hard as I could to the top of a hill hoping to build enough momentum to cruise down the other side.
As I reached the top of the hill and began my descent down the opposite side, I quickly realized I would need to change course.
Apparently, gravity had also “done its thing” with the rain water too. Covering the path at the bottom of the hill was a massive puddle of water. The kind one shouldn’t ride their bike through.
I attempted to steer my bike around the outer right side of the puddle and then make my way back onto the trail. What happened was a little different.
While I succeeded in avoiding the puddle of water, I was unable to steer my bike back onto the trail as planned.
Instead, my front tire slipped in the loose gravel that lined the path. Both the bike and my body came to a halt when I drove my bike into the bushes just off the trail.
I turned around to see another man riding down the hill behind me. He did not acknowledge me standing there in the bushes.
Instead, he gracefully steered his bike around the left side of the puddle and kept right on going. Further evidence that the Danes are better at just about everything.
As for me, I dragged my bike out of the bushes, taking several branches with it. I pulled the thorns out of my jacket sleeve, and hopped back on my bike.
I never found the alpacas.
That time I took the world’s slowest Uber ride (2018)
I stood alone in the rain on the streets of Paris’ Gare de Lyon neighborhood at 3:00 a.m.
I was trying to request an Uber to the airport for my flight to Marrakech, Morocco at 6:00 a.m.
Since it was Paris, and it was 3:00 a.m., people were just finishing up their partying from the night before. So as luck would have it, surge pricing was in effect.
I decided to wait 5 minutes and try Uber again to see if I could get a better deal. It worked.
I managed to save about 15 Euros when a driver finally accepted my ride request. The Uber app told me the driver would arrive in 5 minutes. He did not.
Instead, my driver arrived 15 minutes later even though I could see on the app that he was just around the corner, sitting there, not moving.
Once my driver finally made his way over to pick me up, I hopped in the car and pulled up the directions to the airport. Great, I thought to myself. We’ll be there in about 30 minutes.
What I didn’t know, is that my driver held no sense of urgency whatsoever. Even with the knowledge that he was picking up a passenger at 3:20 in the morning who was headed to an international airport. Nope, no hurry at all.
For the next 45 or so minutes, my driver was the slowest car on the freeway. And this is by a long shot. Cars were flying by at twice our speed, maybe more.
The driver was so focused on using Google translate to ask me mundane questions, that he was swerving all over the road while driving at least 30 mhp below the acceptable speed limit.
I rationalized that if we did eventually veer off the road, there was little chance for injury since we were moving so slowly.
Eventually, I arrived at the airport stressed out, but just in time to be the last one to check my bag in for the flight.
My plane was boarding as I approached the gate, but I had a moment to pick up a quick snack before I got in line to board.
Lesson learned: Always leave at least 30 minutes more than you think you need when taking an Uber to the airport.
This was one of my most worst travel fails, but mostly because of all the stress it caused. I was meeting up with a tour in Morocco, so a missed flight would have been a signficant and costly mistake.
That time I flew to the wrong city in Mexico (2018)
Back in 2018, the boyfriend and I were planning a trip to Mexico. I had always admired the country’s colorful Dia de Los Muertos holiday, so we were planning our visit around that time of year.
While doing my trip research, I learned that Oaxaca was a particulary beautiful place to experience this holiday.
After reading all about the celebrations around the city and the beautiful decorations on display, I booked us a hotel for three nights. The boyfriend was in charge of booking the airfare.
At some point after he booked our flights from Mexico City, but a few weeks before we were to depart, he realized he had booked flights to the wrong destination.
So instead of spending three fabulous nights enjoying the food and culture of Oaxaca, we instead enjoyed the beach life in the coastal city of Huatulco.
In the end, we were happy we got to visit Huatulco, but I never did get my Oaxacan Dia de Los Muertos experience.
That time I got stuck at the airport in Venice (2018)
The boyfriend and I were on our first international trip together in Italy. We had made our way north from Rome and were spending a night in Venice before flying up to Paris for two nights.
Everything I read beforehand about Venice told me it was too touristy, it was not worth visiting, and that the food was terrible. EVERYTHING I READ WAS WRONG.
Venice was amazing.
But anyways, after our day in Venice, we woke up the next morning and headed to the airport for our flight to Paris.
We boarded our flight in the early afternoon. After our plane pulled away from the gate, we proceeded to sit on the tarmac for 3 hours. No joke. We sat there for 3 hours.
In fact, we were stuck on the plane for so long they started beverage service. I believe they even fed us a snack.
After sitting on the tarmac for three hours, they finally brought us back to the gate so we could get off the plane. Needless to say, our flight was cancelled.
As we retrieved our luggage, I called the airline to try and snag a spot on the next flight. I managed to get through rather quickly and was placed on the next departure later that night.
The issue with this whole ordeal though, is that after we were rebooked on the new flight, we ended up just sitting in the airport for the next six hours.
We were stuck in a total dream destination, and elected to just sit in the airport.
The Venice airport is close enough to the city center that we could have easily gone back and explored some more. I really wish we had.
Lesson learned: Don’t spend your day in an airport if you don’t have to. Flights get delayed and cancelled all the time. Don’t let it ruin your day.
That time I broke the toilet (2014)
This is one of my favorite travel fails and favorite travel stories to tell.
I had just spent the past several hours traveling from Puerto Viejo, Costa Rica to Bocas del Toro, Panama. It was a trek that included multiple vans, a border crossing, and even a boat ride.
I had spent the night before drinking wine at a local Italian restaurant with some friends I made. We closed the place down as young backpackers do.
Despite the late night, I was up early and ready to move on to my next destination.
About an hour or so into the trip, my stomach started to bother me. The roads were full of potholes, so the ride was on the bumpy side.
As a result, I was looking forward to getting to my hostel in Panama so I could just relax for a bit.
When I finally arrived at the hostel and got checked in, I was shown to a room with three other bunks.
All the beds were taken except one, so I placed my belongings down on the available bed, then made a bee line for the restroom.
I’ll spare you the details here, but when I went to flush the toilet, it did not flush.
Unsure what to do, I attempted to flush multiple times, pulling the handle in all directions. No luck.
I lifted the lid from the back of the toilet, but nothing looked familiar to me. I know, it’s a toilet, how complicated can it be? But believe me when I tell you, I would have done anything to get that toilet to flush.
With no other options in sight, I accepted defeat. I left the toilet, unflushed, just sitting there.
As my luck seems to go in these situations, as soon as I walked out of the restroom, one of my roommates returned to the room. He walked right into the restroom.
I cringed as I heard him messing around with the toilet. A few moments later it flushed.
I was so embarrassed I did what anybody else would do, I grabbed my belongings and got the heck out of there. No seriously, I picked up my bag and left, never to return again.
I made my way to the other side of the island, unfortunately only a short walk away, and checked into a hotel room. A hotel room with my own bathroom and my own working toilet.
That time I learned what bed bugs are (2014)
I was visiting Puerto Viejo on my first international solo trip back in 2014. I was traveling with some girls I met when I landed in the capital San Jose.
Originally, I had booked a room in a tree house, but upon seeing how to enter said tree house, I asked for a different room.
My new friends and I were offered one of their largest rooms if we wanted to share. The shared room would save us money, so we agreed.
It was an upstairs room with lots of windows and a private balcony with a hammock. It seemed perfect.
We dropped off our things, put on our swimsuits, and headed out to enjoy Puerto Viejo’s beautiful Caribbean beaches.
At night, we returned to our room, got ready for bed, and passed out.
In the morning, my travel partner in the bunk above me asked if anyone else was feeling itchy. We did.
At this point we all crawled out of our beds and started ripping the sheets off our prison style mattresses. We were in a hostel after all.
We all found what we believed to be bed bugs crawling around our mattresses. Our solution? We tossed all three of our mattresses outside on the balcony.
We stood them up in a row against the railing, then proceeded to continue getting ready for the day.
It was as if we thought the bed bugs would realize they were outside now and they were free. Free to escape the confines of our mattresses.
We returned to our room late that night intoxicated from the party at the hostel bar. So we did what any drunk twentysomethings would do. We put our bed bug infested mattresses back on our beds and went to sleep.
The following morning, my bunkmate and I bonded over the bug bites appearing all over our arms and legs.
Was it gross? Yes it was. Did we do anything about it? No we did not.
That time I hiked to the summit of Mt. Whitney with a hangover (2012)
One of my most epic travel fails was the result of some seriously bad decision making.
My boyfriend at the time and I were spending two nights in Lone Pine, California so we could hike Mt. Whitney as an out and back single day hike.
For those of you that don’t know, Mt. Whitney is the tallest peak in the continental USA standing at 14,505 feet tall.
It is also one of the tallest mountains you can climb without moutaineering skills or climbing equipment. The round trip hike is 22 miles and takes anywhere from 12 to 16 hours to complete, depending on one’s fitness level.
It’s a hike one should prepare for well in advance.
One should not however, spend the night before drinking and playing ping pong at the local bar. But that’s exactly what happened.
Predictably late for our sunrise wake up call, we finally set foot on the trail around 8:00 a.m. Much too late to have any hope of returning by nightfall. But that was not the worst part.
It was the hangover that got the best of me.
My pounding headache started to go away after the first two hours or so, but the nausea remained with me for the majority of the day.
As late afternoon approached and the temperature began dropping, I acquired yet another headache. Not a pounding headache, but a dull, constant one.
This my friends, was an altitude headache.
This altitude headache paired perfectly with the nausea, and stuck with me for the remainder of my day.
However, despite these obstacles, I managed to see the summit of that beautiful mountain.
Climbing Mt. Whitney in a single day is an incredibly difficlut feat for most people, but doing it while hungover with an altitude headache is a different beast entirely.
I’m proud of this accomplishment and it remains one of the most stunningly beautiful hikes I’ve ever done in my life.
The views from the summit were worth all the pain I put myself through that day.
If you’re an avid hiker, I encourage you to look into hiking Mt. Whitney. Just please don’t visit the bars the night before. Save yourself from my same travel fails and learn from my mistakes.
That time I booked a rundown motel in the middle of nowhere – (2010)
One of the first trips I ever took by myself was to Washington D.C. to attend a rally on the National Mall.
I booked my flights and reserved a bed in a hostel just a short walk from all the major sights.
Just a few days before my trip, I received a call from the owner of the hostel. He informed me they were cancelling my reservation because they were overbooked and gave my bed to someone else.
I immediately began looking for somewhere else affordable to stay. Since there was a major event happening in the city, all the hostels and affordable hotel rooms were long since sold out.
As a result, I ended up in a run down motel somewhere in Maryland in the middle of nowhere. The hotel was depressing and there was nothing around to do. It was incredibly sad.
To make matters worse, the train ride from where I was in Maryland, to the National Mall in Washington DC, took about 90 minutes each way. If that wasn’t bad enough, my hotel was also a 30 minute walk from the train station.
So I basically had a two hour commute, each way, everyday I was there.
I can’t begin to tell you how bad this sucked and it completely ruined my trip. I spent the majority of my time and money commuting to and from this crappy hotel.
To this day this remains one of my biggest travel fails ever.
I can now look back and laugh at how awful this experience was, but the memory of this trip remains depressing.
I hope you’ve enjoyed reading about my many travel fails and embarrassing moments over the years. If you enjoyed this post, please consider sharing. It really helps me a lot. Thanks for reading.
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Eden FitePart-time Traveler | Dog Lover | Avoider of Crowds
I help people use their vacation days to see the world.
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