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50 Of The Worst (And Most Hilarious) Travel Fails People Ever Experienced

MonicaApril 4, 2022

Let’s be real here; travel fails make some of the best travel stories. They’re stories we want to listen to where everything goes wrong. Typically, these stories involve missed buses, strange illnesses, and chaotic transportation experiences to bucket list destinations.

We compiled 50 of the most hilarious travel fails from around the world for your entertainment. You’ll find stories about crying babies, awkward-angled pillows, and travel photos that are so bad, all you can do is laugh. 

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50. Crying Baby

“I was on a long trip with three transfers and was somehow next to a crying baby on every single flight” (via jimmyfallon). 

Flying is already stressful enough. When you add a crying baby to the mix, it makes it that much worse. Imagine sitting next to a crying baby on a long haul flight? No thank you. Not only that, but imagine it happening three consecutive times? That’s some bad luck, and one of those travel fails that’ll make you never want to travel again.

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49. Massage Went The Wrong Way

This is one of those travel fails that make you cringe. Lying down for a massage is an experience you’d hope would be a good one. Unfortunately, massages can end up being disastrous like this Reddit user experienced. The masseuse licked their foot and they ended up hiding in their hotel the rest of the week. That’s one way to ruin a vacation.

“I was on a pleasant vacation to the Bahamas when I decided that I wanted to get a massage because I had been in the ocean a little too long and my back began to ache. Then I thought that it’d be pretty good to go to a spa and get that done- as it had 4.7 stars with Google Reviews. I ended up leaving mid-massage and hiding in my hotel for the rest of the week because the masseuse licked my foot. Never again” (via BillionDollaBean).

Food Fun Travel

48. I Swear It’s A Neck Pillow!

Seeing this would cause you to take a double or triple take. It looks like this woman has a giant hole in the back of her pants. Fortunately, she’s only holding her beige neck pillow the wrong way. Next time you’re shopping for pillows, make sure you go for a bright green or blue one so this doesn’t happen to you (via Food Fun Travel).

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47. Beach Boys

“Early 2000’s, we were first in line for our SW flight out of Vegas when these older guys with Hawaiian shirts cut in front of us. My friend leans over and was like, “Who do they think they are the effing Beach Boys?” And, that’s how I met the real Beach Boys” (via haats528).

We’ve all made a joke like that time and time again. It’s rare that the joke you make is actually true, like what happened to this Twitter user. Lucky for them, they ended up meeting the real Beach Boys. What an awesome outcome.

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46. How Beautiful

Arriving at the Grand Canyon, only to find it’s shrouded in clouds, is one of those things we pray won’t happen to us. Most people that visit the Grand Canyon have a great experience unlike this Reddit user. Their first time seeing the Grand Canyon was ruined because it was concealed in a layer of clouds. At least it’s still beautiful in a way (via Mr-Xela-48).

Cars.com

45. Bad Connection

“Rental car couldn’t connect to our phones via Bluetooth and didn’t stop trying. We spent the entire road trip listening to a nice robot lady say “I’m sorry, I can’t find you” every 10 minutes” (via BakeRoss1988). 

Radio static is annoying enough, but listening to the robot lady say “I’m sorry, I can’t find you” every 10 minutes might even be more annoying. This is one of those travel fails that make you want to pull over on the side of the road, throw your hands in the air, and give up. 

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44. Paper Organizer

“On my second flight ever, coming back from Japan, I fell asleep during the 14 hour flight. I wake up to find paper laying all over me. The business lady that was sitting next to me used me to organize her papers while working on her laptop as I was sleeping” (via RobertBird37). 

The audacity. Talk about invading personal boundaries. Not only is that not okay, but it’s also incredibly rude. As one of the most random travel fails on this list, we’d hope that most people wouldn’t do this, and would have the social knowledge to know that you don’t use a random sleeping stranger to organize your documents on an airplane.

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43. Grand Tour

“When I was on holiday me and my family booked something called a “grand tour.” It was 4 hours of us sat in a poorly air conditioned bus whilst some dude tells us about pretty much any rock we pass. We did stop every once in a while at some random places in the middle of no where. Most boring day of my life” (via Jamoos123). 

We’ve all had a boring travel experience here and there. This Reddit user shares one of the most boring travel fails on this list, where they went on tour and pretty much stared at rocks for four hours. They must have been ecstatic when the tour was over.

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42. Ferry Ride

“Thought it would be a great idea to take a ferry from Wales to Dublin and back to save a few bucks. What I wasn’t counting on was the wind being too rough for us to dock so I spent 3.5 hours on the floor trying not to puke while we violently swayed in the Irish Sea” (via StuffKRISwrites). 

This doesn’t sound like it was worth the few bucks this Twitter user saved. Unfortunately, they spent a majority of the ferry ride on the floor, trying not to puke. As bad as it sounds, this is one of those travel fails that make a great story in the end. 

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41. First Time

It’s great when a pilot can have a sense of humor, especially when it’s at the cost of someone other than ourselves. This Twitter user was the butt of the pilot’s joke when they admitted they were scared because they were flying for the first time – and the pilot said it’s his first time too. As bad as that sounds, this is definitely one of those travel fails that make your first time flying quite special. 

“My first time flying I was petrified, I met the pilot and told him I was scared. His first announcement was we have a new flier on board today. Don’t worry, it’s my first time too” (via teesa1980). 

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40. Big Ben

“I finally got to see Big Ben” (via chadillac86). 

Big Ben, under construction. At the very least, this Reddit user wasn’t alone. There were probably tons of other people that also shared this experience, as one of the most heartbreaking travel fails on the list. Hopefully they were still able to enjoy London.

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39.  True Crime

“Was listening to a true crime podcast on a train ride. When I got to my stop I realized my headphones hadn’t been plugged in. It had been playing out of my phone the entire time” (via eddielovestoast). 

Maybe the other passengers on the train thanked this Twitter user for the entertainment. This is one of those travel fails that might’ve had a great outcome, even though it’s pretty embarrassing.

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38. Accidents Happen

“We hit some turbulence and a ventriloquist dummy fell out of the overhead compartment and started rolling down the cabin. People thought it was a child in a suit and bowtie and started freaking out” (via MovieNerd15). 

Even though this is pretty terrifying, it’s quite hilarious. Not only did a ventriloquist dummy fall out of the overhead compartment, but everyone thought it was a child rolling down the cabin. This is probably one of the most fortunate travel fails on this list considering it could have been a lot worse.

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37. Smarties

“I always brought smarties with me on planes to keep my 3 young kids busy. A man across the aisle from me was holding a screaming toddler and looking desperate. I handed him a pack of smarties. He immediately ate them himself and said “wow, thank you” (via karenconway21). 

It’s pretty hilarious that this man thought the Smarties were for him. Most of us would have assumed it was for our screaming child, but it looks like the man needed them more than the child did. These are the types of hilarious travel fails that keep us coming back for more. 

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36. Bad Timing

This isn’t something you see every day. Apparently, this was this Reddit user’s mom’s first time in Paris (via OstidTabarnak). We’re all wondering why the building is on fire. At least the mom got a selfie in front of it, and has a memorable story, to say the least.

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35. Airport Ride

“Hitched a ride on a cart transporting people across airport. I was lazy and had no idea those are only for people who actually need them. Mom and son in cart covered for me and told driver we were all “family.” If you see this, hi airport family!” (via Wichitakat). 

Hitchhiking to save money is one thing, but hitchhiking in an airport? That’s unheard of. This Twitter user stepped up their game and decided to hitch a ride on an airport cart. Luckily, she found the right passengers who covered for her. She could’ve boarded with total snitches. That would have been one of those travel fails that might’ve taken a turn for the worse.

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34. Shoes Off

This is one of the most disgusting travel fails on this list, and is something we hope would never happen to us. Not only is it rude, but it’s pretty gross. Has this guy ever heard of hygiene? 

I was on a plane that was almost empty, but this guy decided to sleep on the middle row and took off his shoes….i cannot describe the smell, I wanted to scream. ETA: it was a 12hs flight so yeah“ (via Neonexus-ULTRA).

Twitter

33. Scary Parade

“Was in Germany for Fachnacht, basically Grimms Fairy Tales/Halloween come to life. At a parade and was told “if you get kidnapped, don’t worry they will bring you back” I was terrified, spent the parade thinking I would be taken by creepy German witches and wolves“ (via Jess_icaBrown).

This doesn’t sound like something anyone would voluntarily sign up for. Not only is the idea of getting kidnapped terrifying, but getting kidnapped by German witches and wolves is scary. It makes it one of the creepiest travel fails on this list. 

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32. Trip To Italy

“So me and my family were planning on going to Florence, Italy and my grandma bought the tickets. We had about a week before we left and we noticed she bought tickets to get to Florence, Kentucky” (via D1llyD1lly02). 

This is so cute that it’s forgivable. That poor grandma. This is one of those travel fails that make you want to give that grandma a big hug for trying her best.

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31. New Profile Picture

This Reddit user’s Machu Picchu photo is so bad, it’s hilarious (via Mr_Tom_Yabo ). At least they’ve found their new profile picture with this travel fail. At least we can be certain they saw a lot more while visiting Machu Picchu than this photo shows.

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30. Reindeers

“At a camp in Northern Norway,I take out a reindeer plush toy from my bag and exclaimed to my guide ‘I love reindeers’. My guide ‘We do too, your soup had reindeer meat’”(via OdiousOpinions). 

That’s not something you want to hear after pulling out your reindeer plush toy, especially after having already eaten the soup. Hopefully this Twitter user enjoyed their meal, and this was one of those travel fails that helped broaden their taste palette. 

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29. Not Again!

“My first visit to NYC many years ago, while showering at the hotel, the entire ceiling came down and filled the tub. I narrowly escaped.  And when I called the front desk to complain and get a new room, I heard someone in the background say “Oh no, not again!” (via Jabe373). 

We probably all have a lot of questions, like why this hotel was allowing guests to stay in a room with a broken ceiling. Not only is it incredibly dangerous, but it’s also a health hazard on many different levels. Let’s hope this was one of those travel fails that benefited the Twitter user, and they got a room upgrade for free.

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28. Disney World Allergy

Have you ever been so excited you broke out in hives? Apparently, it’s a thing. This Reddit user shared their experience being so excited about going to Disney World, that their immune system attacked itself and they ended up having a miserable time. This is one of the most surprising travel fails we’ve heard of.

When I was 8 years old I got so excited about going to Disney World down in Florida, my immune system began attacking itself. I broke out in hives all over my body and I dragged the entire experience down because I was so sick and miserable. I am literally allergic to feeling an extreme emotion such as sheer giddy excitement lol“ (via Sgt_Frank_Woods).

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27. Still Looks Cool

This is one of those travel fails that’s so similar to the Grand Canyon fail, it seems to happen more often than not. Even though this Reddit user couldn’t see anything, the Gateway Arch still looks pretty cool. 

“Visited St. Louis for the first time and was told I had to see the famous Gateway Arch” (via drtythrtybass). 

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26. Crying

“I was on a flight from the Philippines to London, about 15 hours.  There were seven children under the age of 4 all around me.  There was not a moment someone wasn’t crying.  Most of the time, it was me” (via Robert_P_Wulff). 

We’d probably cry, too. Another Twitter user shared a similar experience with crying children on a long haul airplane. It seems these children save their tantrums for the worst possible time – like airplanes.

Food Fun Travel

25. A “Friendly” Bite

This isn’t something you see every day. A camel bite to the face just sounds unpleasant, but at least it’s one of those travel fails that make a great story (via Food Fun Travel).

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24. The Devil’s Bridge

“Rented a car and took a 2 hour drive outside of Berlin to see die rakotzbrücke just to discover the water was drained and the whole area is under construction” (via topsecretvcr). 

This is one of those travel fails that just breaks your heart. Imagine spending all that time, money, and effort to visit a place, only to find it’s shut down? Hopefully this Reddit user found something else to do instead.

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23. Missing Kid

“When I was 10 my family forgot me at Mount Rushmore during a cross country trip. I took the whole tour on my own and figured I’d meet them at the exit when I was done. They realized I was missing two hours after they’d left” (via theoneclark77). 

Talk about Home Alone. This family forgot about their 10-year-old kid. That’s pretty shocking, to say the least, and is one of those travel fails you hope would never happen again. At least the family probably felt pretty guilty. 

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22. Sumo Competition

“In a hostel in Kyoto found out about a big sumo competition the next morning in Osaka. Got up at like 5am and went to Osaka to try to attend, only to find it sold out. There was only one hostel with capacity left on town, went there and it turned out a lot of the sumo wrestlers were staying there. Sat up watching Sumo on TV at a hostel with Sumo wrestlers. Next morning they invited me and my friend to their private practice that was definitely not for the public” (via HowardPrime). 

This is one of the best travel fails on the list. Not only did this Reddit user get to watch Sumo on TV with the wrestlers, but they also got to go to a private practice. This definitely beats the big sumo competition. 

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21. Rude Uber

“If your @Uber driver calls you before they arrive and says “I’m almost there, where do you want to go?” Don’t tell them. As soon as I answered he hung up and cancelled the trip” (via zacjmclean). 

There are some things you tell Uber drivers, and some things you don’t. Like, your destination, before getting into the Uber. That’s a pretty mean thing for an Uber driver to do. Let’s hope this Twitter user found another Uber ride and made it to their destination safely and on time.  

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20. No Shoes

“Parents wake me up before sun rise so we can go to Six Flags. I get dressed and brush my teeth and all that and proceed to get in the backseat of the van and immediately fall asleep. I wake up like an hour later and realize we are almost there and that I forgot to put on shoes. My parents were pissed and we had to go buy me another pair” (via mrghostwork). 

This is one of the most innocent travel fails on this list. This kid was so excited, they forgot to bring their shoes to Six Flags. At least they didn’t break out in hives, like the other Reddit user did. 

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19. The Best View Of Paris

Another incredible view, shrouded by clouds. This husband and wife expected something totally different when they visited the Eiffel Tower for their honeymoon (via theadum). Let’s hope they were still able to enjoy Paris, regardless of the weather.

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18. Coat Bag

“Coming back to Canada in January from Mexico I said to my wife “imagine if they lost our coat bag”.  After 3 hours of intense questioning and luggage ransacking they realized I did not say “imagine if they lost our coke bag” (via Travisjpick). 

This is one of those travel fails that you think would never happen, but actually does. Unfortunately for this Twitter user, immigration misheard them and ended up ransacking their backpack in the hopes of finding drugs. Luckily, they made it out okay. 

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17. All-Inclusive

“Decades ago, on my first international flight: My seat mate took all that was offered to him—wine, steak dinner, cocktails. I declined everything, thinking it would cost a fortune. At the end of the flight I asked him the cost. He said, “My good man it’s all included!”” (via ArthurAlbertTV). 

We can all relate with this Twitter user. We’ve all declined fancy meals or drinks once and a while to save money. Unfortunately for this Twitter user, it was all included. They could’ve treated themselves to luxurious decadence, for free!

Sharkcrew

16. Shark Attack

“I was beach fishing on Restoration Island in Queensland, Australia. The person who I was with landed a small shark. I was helping hold down the shark while she removed the hook so she could release him. Just when she got the hook out the shark flipped around and grabbed my hand in its mouth. My hand was OK. I felt the true meaning of adrenaline rush and really threw that shark back into the reef” (via ordinaryknitter). 

That’s terrifying! You’d never expect a shark attack to happen out of the water, let alone when you’re releasing a hook. Luckily, this Reddit user’s hand was okay, and they pretty much made it out unscathed.

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15. Photobomb!

This is one of the cutest travel fails on this list. It’s not so much a failure as a great travel memory. Meeting a friendly stingray on vacation is pretty rare (via kebulatr).

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14. Cabin In The Woods

As terrifying as this is, it’s quite hilarious. You’d never expect a bear to be knocking on your door. It seems this Twitter user was pretty nonchalant about the whole thing, and found it humorous. This is one of those travel fails that make a great story in the end. 

“Rented a cabin in the woods I heard a loud knock on the door, I yelled I’m in the shower! Pounding continued, and yelled I’m in the shower! I come out to see and it was a bear trying to knock down the door! I guess he wanted to take a shower too” (via DannyUnchained1). 

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13. DIY Elephant

As one of the strangest travel fails on this list, a DIY elephant is something none of us have probably ever seen before. When you can’t afford an elephant, just make your own. Add a trunk to a cow, and you instantly have your very own elephant (via Food Fun Travel).

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12. Photo For Reference

“Traveled​ to Wittenberg, Germany in 2011. The door Martin Luther nailed the 95 Thesis to was being restored” (via Trowj). 

This is definitely cringe worthy! At least they had a photo reference to look at, even though, in a way, it makes it worse. It’s not something you’d expect to see, much like the other Reddit user who had a similar experience visiting The Devil’s Bridge. These travel fails keep happening, but they make great stories.

Wikipedia

11. The Hotel Next Door

“I got into a taxi and asked the driver to take me to my hotel. He pointed across the street and said “There it is”. I got out and walked to it“ (via DaSkrambledEgg). 

At least this taxi driver canceled the ride for a good reason, unlike the Uber driver from above. This is hilarious, and is something we can all relate to. Being in a new city is already stressful enough, so adding an embarrassing experience to the mix makes it much worse.

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10. Almost There

Bad travel photos can be so funny that they’re sometimes better than good travel photos. This person missed the sun by a few inches, but it still made for a great picture (via Food Fun Travel).

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9. Air Sax

“In high school, our marching band, which I was in, got to go to Sea World Orlando to perform. It was my freshman year.  Long story short, we were on a bus for 12 hours, got off and I realized no one packed my instrument. So, I played air sax in front of hundreds” (via mikefreeman1012). 

This Twitter user was able to make light of the situation by playing “air sax.” It’s such a bad travel fail, that it’s hilarious. At least they were still able to join in on the performance!

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8. Cheesecake

“Guy next to me on the plane was sound asleep.  The cheesecake I was served flipped out of the container when I opened it and landed in his lap.  Had to clean it off for him while he slept.  He was a bit surprised by the remaining mess on his pants when he woke up” (via haugl76). 

At least this Twitter user helped clean up the passenger, instead of the other person who used their seat mate as a paper organizer. Still, this is one of those travel fails that are so bad, all you can do is laugh. 

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7. Beautiful View

Another view, concealed by bad weather. We’re seeing a pattern here. These travel fails, although unfortunate, are funny enough to make a good travel story. Hopefully this Reddit user was able to make the trip a second time.

“Woke up at 230AM to make a 2 hour drive up 10000 feet to see the sunrise atop Haleakala. Have you ever seen such beauty?” (via bradp36)

Reddit

6. Nice Trees

“My friend is on vacation in Hawaii, and she asked this man to take a picture of her. He told her, “I got a close up.” Bless this man” (via f43cm0). 

Even though this is a horrible photo, it’s too funny not to love. At least he managed to get her head in the photo. The trees look great, too.

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5. Fast Ride

“Traveling with my parents, my dad took a break reading the paper. Mom was driving. She yelled out, “This guy must be going at least 100.” Dad said who? Mom said” The guy I’m passing!!”” (via mamamarshall2). 

This mom likes to drive fast – too fast. She had to break 100 mph in order to pass the other driver, which is something you don’t want to hear while in a car as a passenger. 

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4. You’ll Always Have The Memories

“120 mile solo hike. Asked an elderly passerby to take a photo for me. I checked it right away but he struggled enough with the touch screen that I didn’t ask him to take another” (via Reddit).

This is another photo that’s so bad, it’s hilarious. At least he managed to capture him from the head down, and he has some sort of photo for his memory bank

Food Fun Travel

3. Lost In Translation

Translation fails are some of the best travel fails out there. Visiting a “garden with curled poo” is not something that’s high on our to-do list. We can assume it was more beautiful than the sign suggests, though (via Food Fun Travel).

Twitter

2. Airport Twins

“Ran into this guy at a JFK terminal bar. What are the odds we are wearing the same outfit?!  No idea who he is. Had to get a pic” (via timhartin).

This is such a great travel fail that it’s definitely picture worthy. It’s not even like they’re both wearing blue sweaters either, they’re both wearing bright orange sweaters, a color you don’t see often.

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1. Taj Mahal

This is one of the most unfortunate travel fails on this list. Similar to the Eiffel Tower and Grand Canyon, this person went to see the Taj Mahal, only to find it covered with clouds. Let’s hope they were able to go the following day! 

“Went to see the Taj Mahal this morning.” (via SnowWonder )

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