Oops!: 20 Crazy Travel Fails by Travel Bloggers

Travel: it's always interesting, even if it's not always perfect.

From missed flights to rental car issues to strange encounters with locals, there's always something that could go wrong while you're traveling. Whether that travel fail makes or breaks your trip is up to how to deal with it: some travel fails can turn into the best times.


These 20 travel bloggers (including yours truly) share their top travel fails and what they've learned from each. These stories might have been stressful while they were occurring, but they're sure fun to read after the fact!

Natalie, Cosmos Mariners: Destination Unknown

At author A.A. Milne's house in London

My own travel fail happened on my first trip to England (many more years than I'd like to admit). My parents, sister, and I were going to take the train from our hotel London to the airport, which seems like a pretty simple task.

We bought tickets for the next train out and hurried over to the terminal, only to see that train pulling out of the station as we walked up. We figured that we'd just wait for the next one to leave and checked the schedule for the next train to the airport.

That next train started boarding pretty quickly; we were getting a little panicky at this point since our airport transport was taking longer than we expected. We all piled all and prepared for a quick trip to the airport, but, once the train got underway, it began to stop every five minutes. We didn't realize that some of the trains between the station and Gatwick were locals!

The train trip took much, much longer than we'd planned, and we were terrified that we were going to miss our plane. The four of us booked it through Gatwick to get to our gate...only to see our flight leaving without us. After a lot of waiting around and giving the airline employees puppy dog eyes, we managed to fly standby on the next flight back to Atlanta. We arrived many, many hours past our original arrival time, and I've learned to 1) always check the train departure times ahead of getting to the station, and 2) always check what type of train I'm taking!

Nishaa Sharma, NishaaSharma.com

{photo courtesy of NishaaSharma.com}

I read a map upside down while I was in Brisbane this June, which is enough of a travel fail on its own, and ended up running a few minutes late for the Koala Sanctuary tour I was supposed to catch.

So, I started jogging down the dock to make sure I didn't miss my boat, and ended up dropping my phone (almost in the water), tripping and face planting in front of everyone- including a very cute skipper! Luckily I made the boat, we were all able to laugh it off, and ended up exchanging information with the skipper at the end of the day. I guess it made a solid first impression!

Allison Miller, Tornadough Alli 

{photo courtesy of Tornadough Alli}

We were riding down the Deuce in Las Vegas and the guy in the seat next to us was chanting and doing hand signals up and down and laughing uncontrollably to himself. Needless to say we were walking after that.

Rachel G, The Random Writings

Angel and I with our train tickets in hand as we wait for our train back to Michigan {photo courtesy of The Random Writings}

I, my husband, and my two younger siblings wanted to spend a weekend visiting Chicago. My Grandpa suggested that we borrow his car, a Buick Park Avenue that was 5 years younger than my own car (12 instead of 17 years old), for the trip--he just wanted his four oldest grandkids to be as safe as possible on the road. We had a fun weekend, visiting friends and family in Chicago and seeing the sights.

 We had just left the Museum of Science and Industry and were about to head home late Sunday afternoon when we were waiting at a red light. The light turned green, the husband stepped on the gas, and the car didn't move. There we were, at a busy intersection in Chicago, with a car that wouldn't move. Cars were honking at us, I was yelling out instructions as if I knew something about cars--it was intensely stressful.

 We eventually got the car over to the side of the road, and went through the whole call insurance, call a tow truck, wait one hour for a tow truck deal. When we got the car into a GM dealership, their quick inspection revealed that we needed a new transmission. But the dealership was closing, and we were hours away from home. We took our luggage and walked about 10 blocks to a 24-hour McDonald's that we found via GPS. In the wintry weather of March.

 The saga ended with us taking Amtrak home in order to get home in time for work and school, and my Grandpa having to drive out to Chicago with his brother and a flatbed trailer to pick up the transmission-less car and bring it home.

Tamar, Portjam & Co.

Tamar at her hotel {photo courtesy of Portjam & Co.}

I was working a lot before heading on my trip earlier this year. I lingered and booked my hotel for my Panama layover 4 days in advance and requested airport transport from the hotel. I got to PTY airport and was expecting to see a driver holding my name on a piece of cardboard, but no one was there. I checked my email to see if I got a confirmation from the hotel, and found an email asking me to rate my stay at the hotel.

It turns out I had booked the hotel for 3 days before my arrival! I winged it and explained the whole thing to the hotel clerks, and they remembered my name and honoured my reservation. A fail turned into a win with some amazing hotel staff!

Gemma, Two Scots Abroad

{photo courtesy of Two Scots Abroad}

Craig and I checked in at Bogota airport, sunny Santa Marta here we come! The sales advisor wrote down gate 15 on the ticket so off we toddled. We were super hungover so I had a wee nap only to wake up with a strange feeling - no one had moved yet. Craig checked the board, gate 15 was correct.

An hour passes (I nap) and Craig doubles checks. He comes back stressed – it was the wrong gate, we had heard no tannoy message and as a result of this missed the flight. Do not party the night before a flight and don't list to Viva Colombia!

On a positive note, I had left a handmade ring (by a good friend for graduation) at the X-ray machines, and I managed to get it back. Craig now refers to that piece of jewellery as the one that cost us two flights.

Toni Rynne, Love in Brisbane

Toni and her husband just moments before their travel fail {photo courtesy of Love in Brisbane}

My husband and I were travelling around India and we were staying in a old palace in the middle of nowhere. As we walked out of our room my partner jumped down a couple stairs and landed in a hole. He hurt his ankle and couldn't come with me to any of the other amazing places for the next few days.

When we got back to Australia two weeks later, it turned out that he had broken his ankle. Plus, only 48 hours before obtaining the ankle injury he was attacked by a cow! The crazy creature stuck its horns under his legs and flicked him up into the air.

Kaci Alvarez, Earth to Kace

Kaci in South Africa {photo courtesy of Earth to Kace}

My biggest traveling fail would have to be when I went to South Africa this past summer to visit my boyfriend and his family. It was my first time traveling by myself and it was a total of 38 hours (flights & layovers). My stupid self couldn't get any sleep that entire time but on top of that, I didn't eat at all either. On my last stretch of the flight, I got so sick from exhaustion, the plane start spinning and I threw up before we even took off! How embarrassing!

Shane, Sea Salt Secrets

Shane (left) while in Singapore {photo courtesy of Sea Salt Secrets}

A few months ago, I took my first solo trip. I chose a simple country to test the waters, as I had heard that Singapore was culturally similar to America and the majority of people spoke English. I honestly didn't prepare myself for a big cultural shock.

Within my 3 short days in Singapore, I was fined $1000 for chewing gum and got told by a local that I'd better toss out my coffee I was sipping because food and drink is banned on the trains. Cocktails were $27 as alcohol is highly regulated with a "sin tax"... but I just had to indulge in a legendary Singapore Sling. I wasn't in Sydney...or America anymore.

Katherine Belarmino, Travel the World

{photo courtesy of Travel the World}

My biggest travel fail happened on our honeymoon 11 years ago. We had started in London and were headed out into the English countryside for a few days. I rented a car under my husband’s name, as he would be driving, but used my credit card. We arrived at the car rental office in the middle of the city 10 minutes before closing and found out that I would have to drive, something I wasn’t prepared for, since it was my credit card.

I drove two blocks, stopped to pick up a map from a corner store, and then continued to drive the remaining six or so blocks to our hotel. There was construction on the side of the road barricaded by barriers with little metal feet that stuck out into the road. It was a narrow London street, there was traffic coming towards me, and I wasn’t used to driving on the wrong side of the road and on the wrong side of the car.

Ba-bump-ba-bump. Rome rolled down the window. Psssssssssssssss: the fateful sound of air leaving tires. I had driven too close to the barriers and barely rolled over them with both tires on the left side of the car. Both tires were punctured and flat, so the spare in the trunk wasn’t going to help. By this time the car rental office was closed.

It took me 10 minutes to figure out how to dial the company with my American cell phone. We had to wait for them to send a tow truck through rush hour London traffic and drive us to the car rental at the Heathrow airport. Luckily we had paid for the extra insurance which covered the tires. When they gave us our new rental car the girl at the counter said since Rome’s name was on the agreement, he could drive after all, which he did for the rest of the trip.

Christianna, Expecto Adventures

{photo courtesy of Expecto Adventures}

I took a spur of the moment trip to Maui a few months back, without doing any prior research or planning. The day before my flight, I booked a hotel, despite low reviews, because there was little else available on the island.

When I arrived there, I was shocked to see how run-down it was, and in a such shady neighborhood. I decided to give it a shot, but had to leave after I sat down on the mattress and cockroaches scurried out!

Unfortunately, everything was already booked, so I ended up renting a mini-van and sleeping in it instead. The rest of the trip was great though!

Tamara Elliott, Globe Guide

{photo courtesy of Globe Guide}

My biggest travel fail was getting stuck without money at the very end of my first big trip: a seven week jaunt through Europe when I was 20. My finances were in great shape throughout the trip, and I’d worked it out so I would have just enough cash to get through Belgium, my last stop before heading home.

Unfortunately, when I arrived at my hostel one rainy evening, the front-desk informed me that since I was only staying for a couple of nights I’d have to pay in cash. Problem is, I didn’t have enough cash on me OR in the bank to cover it as I'd been planning to use my credit card.

After some negotiating I gave them all of my money minus about 10€ and promised I’d have the rest for them the next day. I hopped on MSN Messenger (yup, I’m old) and luckily my friend was online and I explained my predicament to her in a panic. She ended up getting her mom to call my mom, who then rushed to a bank to deposit money for me. Of course, it wouldn’t be accessible until the next day, so I only had 10€ to get through the night.

Luckily it was 2 for 1 drink night so I managed to get something to eat AND a couple of bevys—although I had a long walk back to the hostel late at night since I didn’t have money left over for a cab!

Stefan and Sebastien, Nomadic Boys

{photo courtesy of Nomadic Boys}

Our travel fail was on Rinca Island in the Komodo National Park in September. This is the home of the famous Komodo Dragons and the park wardens use long wooden sticks just in case the dragons get too close. The dragons are very docile but if they get too close, they can be quite nasty!

Sebastien was always a bit nervous coming here as he'd read and heard so much about how dangerous the Komodo Dragons can be. Poor Stefan was trying to be all sweet and loving to nervous Sebastien and went to surprise him with a hug. Unfortunately, nervous Sebastien thought this was a dragon and he reacted by grabbing one of the park warden's sticks and tried to fight Stefan off! FAIL for poor loving Stefan :(

Charles McCool, McCool Travel

{photo courtesy of McCool Travel}

The Capela dos Ossos (Chapel of Bones) in Evora, Portugal is certainly one of the most heart-pounding places I have been. My girlfriend (now wife!) and I were awed, repulsed, and fascinated by nearly 500 year old skulls and human bones covering every inch of the Medieval chapel. Although the Capela is chilling (literally AND figuratively), the scariest part happened afterwards.

We returned to the town plaza to find our car missing. After trying to communicate with locals, we went to the police station. The first two Policia looked at us like we were crazed foreigners. Oh, I suppose we were. The third guy spoke the tiniest English and, after hearing our story, laughed heartily. He said, "Policia came, everyone move cars, your car no move." So our car was towed, I paid a small fee, and I have a great story.

Jonathan and Kach, Two Monkeys Travel Group

{photo courtesy of Two Monkeys Travel Group}

We had a plan - Patagonia and Torres de Alpine, to trek the famous ‘O Circuit.’ What we didn’t know, was that the ferry was booked out and the only way to get there was through Argentina (no visa) or fly (way too expensive). So, we failed, due to a lack of research and a go-with-the-flow attitude, which usually serves us pretty well. Someone suggested another option, a three day ferry to the Aysen region of Patagonia, which we’d never heard of before. We had nothing to lose, so why not?!

It turned out to be the best trip of our lives - hiking and hitch hiking down the Careterra Austral all the way from Coyhaique to Villa O’Higgins, the literal end of the road in Chile! We hitched in cars, pickup trucks, flat-bed wagons and trucks and incredible people, all the while surrounded by 360 degrees of awe-inspiring scenery, every step of the way! So our biggest fail, turned out to be our biggest win!

Duke Stewart, Duke Stewart Writes

{photo courtesy of Duke Stewart}

My wife and I are four hours into traveling to the airport in Incheon (Korea) after a soju-fueled night out with our boss, and our trans-pacific flight leaves in a couple of hours. I check my passport but can’t find it. My wife realizes what’s going on and is furious with me for overlooking such a thing. The search escalates over the next couple of hours and we check everywhere, becoming more nervous with each passing minute.

The train stops at the airport and we have one last look through all of our bags. My wife pops open our big suitcase and magically, the passport is there just sitting out in the open. She throws it at me and as it hits the ground, I realize that this was an easily avoidable travel fail. From now on, I’ll always make sure things are in order and will never leave before everything is in place.

Jub Bryant, Tiki Touring Kiwi

{photo courtesy of Tiki Touring Kiwi}

After a few too many Bahama Mama cocktails the night before, I missed my flight from Nassau to Miami. After eventually waking up, I was straight off to the airport. “First flight to Florida, please.”

Little did this small town kiwi (me) on his second trip overseas consider that there would be more than one international airport in each state.

A couple hours later, I landed...in Fort Lauderdale airport. Fail. I got to Miami Airport as fast as public transport let me, but forked out more cash after missing my Miami to Los Angeles flight. Fail.

Luckily I made the Los Angeles to Auckland flight. An expensive night of Bahama Mamas: $850 more than I’d budgeted. Ouch.

Clemens Sehi, Anekdotique 

{photo courtesy of Anekdotique}

A couple of years ago, I went from Jerusalem to the Dead Sea by a local bus. It was late afternoon when I arrived, and I actually did not plan how I would get back to the city. After I spent some time wandering around the place, I went back to the only street connecting Eilat in the Red Sea in the South with Jerusalem and Jericho. But there was no bus.

I waited for over an hour but there still was no bus. I ran out of water, it was getting dark, and I actually began to panic a bit. So, I decided to hitchhike. And that’s what I did. After another 30 minutes, two weird guys stopped in an old broken car with a random young girl in the back and took me back to the main crossing of Jericho and Jerusalem.

Years later, I pretty much know for sure that they were drug or weapon smugglers. But hey, I survived hitchhiking though the West Bank.

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What's your travel fail? Share in the comments!

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