Posted in:

Oakland airport baggage carousel

For the most part, traveling is great and wonderful and rejuvenating and transforming and so many more things. But let’s be honest: It can also lead to embarrassing situations, even if you travel all the time. And while those stories are humiliating in the moment, they’re often hilarious in retrospect — and can teach you many lessons about how to travel better in the future. Here, our Yahoo Travel Explorers reveal the worst travel fails they’ve ever experienced. Get ready to laugh with them (and, okay, also a little bit at them).

1.  The Insect Outburst  

“I was in Sri Lanka, staying in a hostel. It was set around a courtyard restaurant, with bedrooms at one end, bathrooms at the other. One morning, while taking a shower, I discovered a dead cockroach lying to the side of the shower. Cockroaches don’t bother me much, but I figured it might be creepy to other residents, so when I finished my shower, I picked it up to remove it. Alas. The sneaky cockroach wasn’t dead; it was simply on its back and unable to move. It sprang alive and ran up my arm.


To this day, I have no idea why my reaction was to run out of the bathroom, but I did. I ran out of the shower, totally, totally naked, with a cockroach running all over my body. The restaurant was full and much to my horror, everyone turned to stare at me. Again, dear readers, I was naked, flailing around with a cockroach running all over me. Oh dear Lord. I managed to get the cockroach off me, retreated to the bathroom to attempt to find an escape route that didn’t include walking back into the courtyard. There wasn’t one. I had to walk back out, to a courtyard full of applause. Ugh.” —Lucy Hemmings

Related: Man Documents Saddest Vacation Ever with Hilarious Photos

2. The Baggage Bummer  

“I never check my bags, but on a recent trip to Turkey, I was flying business class and didn’t want to carry my bulky backpack on the plane, so I checked it. I got all the way outside the airport to our shuttle before I realized I was missing something. I immediately had to go back in the airport to try to find it. I had to go back through security and be escorted inside, where my bag had just come out onto the baggage carousel. The whole thing took fewer than five minutes, but it was definitely a lesson learned! If you check a bag, don’t forget to pick it up!” — Jackie Laulainen 

3. The Whale of a Time 

“One time when I was traveling in Bali, I came across some Chileans and wanted to show off my Spanish skills (I used to live in Argentina). In conversation, we somehow got on the topic of whale watching. But instead of using the word for whale, I accidentally used the word for … the female nether region. Let’s just say things got pretty confusing at that point.” — Megan Snedden 

4. The Flash Faux-Pas  

“I was invited to Club Med Opio in Provence, and signed up for a relaxing massage. I arrived for my appointment, and one of the pretty receptionists handed me a robe and showed me to the men’s locker room. I put my clothes in a locker, donned the robe and went out to the waiting room. My masseuse was a woman, and she escorted me to the room and said something in French, which I didn’t understand, and then said, “Voila.”

Usually, after being led into the treatment room, the masseuse steps out so you can get your naked body on the table and under a towel so no one has to witness what’s beneath the robe. But when she said, “Voila!” again and motioned for me to get on the table, I gathered she was telling me to drop the towel and hoist my naked self up onto the table. I didn’t want to look like a prude American, so I did as I was told and…dropped the towel. WOA! After I let it all hang out, she let out a little scream and quickly turned around. I instantly grabbed the paper covering from the table and covered you-know-who. With her back to me and one hand over her eyes, she handed me some paper underwear. It turned out that the women at the front desk had “forgotten” to give me this important cover-up.

To make matters even worse, their disposable underwear turned out to be a black thong! Nice little French flair, right? Wrong! I’ve never worn a thong before so I wasn’t quite sure which way it went on until I put it on the wrong way. Trust me, you’ll know. When I finally put it on the right way, I felt more naked than when I was actually naked. That was one massage I will never forget.” — Johnny Jet 

Related: Biggest Mistakes People Make When Traveling

5. The Mis-cow-culation 

“I was filming a travel video at Hong Kong’s Lantau Island. My team, Borderless Media, thought it would be visually interesting if I gave out flowers to locals, and to the big Tian Tan Buddha statue. Unfortunately, we didn’t realize that there were feral cows on the island… until a group of them ran over, surrounded me, and tried to eat my bouquet of flowers! I managed to escape from the hungry cows with only a few missing flowers, and some hilarious clips for the blooper reel.” — La Carmina

6. The Moped Mistake 

“When I heard that I would be riding a moped around the island of Bermuda, I didn’t think twice about my safety. And then I ran into a wall. It all happened so fast. I was riding with a small group, and as we were turning left out of a parking lot I revved the throttle too hard, and crashed into the concrete wall in front of me. Thankfully, I wasn’t injured…but my ego was bruised. The rest of the group checked to make sure I was ok before we all burst out in laughter.” — Brittany Jones-Cooper  

Related: WATCH: I Crashed My Moped Into a Wall: 9 Ways to Learn From My Stupidity

7. The iPhone Fail 

“I always get such terrible jet lag. I’d just spent two days in Vancouver, and was in the airport on my way to Whitehorse in Yukon, and it was hitting hard. I arrived at the gate just in time for the boarding call. I walked up to the lady at the gate and gave her my boarding pass. ‘May I see your ID please?’ she asked with a smile. I took it out of my pocket and gave it to her. She looked at it and turned her gaze to me. I instantly noticed the puzzled expression on her face. “I need to see your ID,” she repeated. I opened my mouth to say that I’d just given it to her when I noticed what was in her hand… my iPhone!” — Keith Jenkins 

Related: 10 Stupid Mistakes You Need to Stop Making on Vacation

8.  The Haggling Horror  

“I negotiated with a boat family in Vietnam who lived aboard their twelve-foot wooden skiff in a tiny bay. They had no sewage facilitates, no running water, and only a tarp to cover them in the rainy season. I haggled with the mother of small children over the price of fresh crab. As we pulled away from the skiff, the woman called out, ‘Lady, you cheap.’ Years after our encounter, I am still ashamed of myself. I should have paid the full asking price. It wasn’t much. The extra income would have made a big difference in their lives.” — Marybeth Bond 

9. The Snake Mistake 

“I have so many embarrassing travel moments, but one that still haunts me happened in Kenya. I was staying with a family in Ngong Hills, outside of Nairobi. I awoke one morning as usual and made my way to the restroom where I unwittingly shared the toilet with a black snake of unknown species and origin. (I didn’t have my glasses on.) When I reached to flush and saw the serpent perched on the back of the seat, I alerted the household and it sent everyone into a comical freakout.

I was so pleased to have survived my snake encounter, for the next few weeks, I told every Kenyan I could about my crazy and hilarious brush with the snake. I didn’t learn until my last day in Kenya that snakes are considered a very bad omen to these folks, and the fact that it showed up in the house right about the time I did… well, it cast some serious doubts on my character! I’d essentially alerted every new friend I met for two weeks that I was a wicked snake woman with bad intentions. Whoops!” —Angie Orth 

10. The Accidental Thief 

“The first time I arrived in Hawaii, I was so excited to be there and see my friend who picked me up at the airport, I grabbed my luggage as soon as it came out and off we went. We spent the whole day driving around and taking photos seeing sights. Strangely, I got a few phone calls from a number I didn’t recognize, so I just ignored it.

After  dinner that night, I was ready to go to bed, and I opened my suitcase — but it wasn’t my suitcase. It was my exact model and color of Eagle Creek suitcase, but didn’t have my tag on it!  I quickly found out that the person trying to call me was the person whose luggage I had picked up. She got my number, name and email from my business card on my luggage tag of my suitcase, which was sitting there going round and round the luggage carousel.  I also had an email from her trying to get a hold of me. She had read all about me on my blog by then, and basically said, ‘How can you call yourself a professional traveler when you pick up someone else’s bag?!’ I was so embarrassed. Now I ALWAYS look at the tag on my luggage two or three times!” — Sherry Ott 

Search For Best Hotels Deals

Search For Best Hotel Deals

Search For Best Flight Deals

Search For Best Hotel Deals

Search For Best Vacation Deals

Search For Best Cruise Deals

View Another Post