Even with meticulous planning, sometimes your travel adventures will go off the rails. These travelers encountered the unexpected and had to roll with it.
What’s your funniest travel story? It could be something that happened at the airport, during a tour, an interaction you had with a local, or any experience that was unusual and makes you laugh when you think about it.
Eight travel experts shared some of the most memorable moments they’ve come across during their adventures. Let’s check ’em out!
Unexpected Luxury in a Snowstorm
Years ago, when I was 18, I went on a tour in Europe. I was a poor university student, so I had scraped some money together. Like a lot of people, I had to make the dreaded phone call to the “bank of Mum and Dad” to ask for some extra money (as I had spent mine on essentials such as alcohol). I had finished my tour in France and had no money to get back to London (where my sister was living at the time). My father booked the cheapest flight he could find (and I set out to the airport with my last 25 euros in hand).
The night of the flight, Europe had a huge snowstorm, and when I got to the airport, we were informed that all flights were canceled and that they were giving us hotel vouchers. I jumped on a bus, ended up at a hotel, and was informed that they only had the suites left, so still with my 25 euros, I moved my stuff into a 450-euro-per-night hotel. They also provided us with drinks and food vouchers.
Downstairs was a great party; the hotel was full. I got chatting with a middle-aged couple, and they asked me to join them for dinner. The husband, Peter, also suggested we should nip out and have some cigars and scotch in the snow. The next morning, we were all heading to the airport, and I just happened to be sitting in a seat next to the couple from the night before. We had a few drinks on the flight and got back to London.
As I was leaving the airport, I realized I didn’t have enough to purchase a tube ticket to my accommodation. Peter noticed this and asked if I would like a lift home. Next minute, we are waiting for valet parking, and this amazing sports car turns up. On the way home, they took me for a tour of London, and they dropped me off at my sister’s door.
My sister made me empty my pockets. At the time, I had under 5 euros left. She asked how I got back home, and I had to confess that I managed to get from Paris to London, stay in an expensive hotel suite including meals and wine, travel in a luxury Jag (with some beers at a pub along the way), all for just over 20 euros.
Ross Muller, Business Owner and Guide, Vino Rosso Tours
A Night With Gecko Roommates
I was traveling solo in Chiapas, Mexico, and opted to try out a local mom-and-pop hotel. I returned to my room after a day of exploring, only to find a family of geckos had moved in. They were all over the place—on the walls, on the ceiling, even on my bed! It was a comedy of errors trying to catch them. I practically slipped on the tile and almost knocked over a lamp; at one point, I even started speaking to them as if they could hear me.
In the end, I accepted this fact and went to bed with my new “roommates.” The geckos were not dangerous at all; quite the contrary, there was something oddly soothing about their presence. Now, I just laugh whenever it comes to my mind about what a night it was. It serves as a reminder that the most memorable aspects of travel are the unplanned adventures.
Alex Veka, Founder, Vibe Adventures
Lost in Translation on the U-Bahn
Once, during a trip to Munich, I had learned just enough German to get by, or so I thought. One day, while navigating the U-Bahn (the subway), I was approached by some friendly, elderly Bavarians from the countryside. Mistaking me for a local, they asked how to buy tickets.
Armed with my very limited German, I attempted to guide them through the process. It turned into quite the spectacle as I could only manage one- to two-word instructions: “Press here,” then “Press here,” followed by “Push here,” and finally, “Money here.” My confidence grew with each word, but little did I realize how this sounded.
When I finished, I noticed their puzzled looks shift to sympathetic smiles. It dawned on me that they thought I was mentally challenged rather than a foreigner. They began showering me with praises, telling me what a “super” job I had done and “how special I was.” One even patted me on the back and handed me a lollipop.
And you know what? It was a really good lollipop!
Martin Wagner, COO & Co-Founder, Go Real Travel
Surprise Parachute Jump on Hike
I once had a guest book a guided hike with me. He joined another party of three that had booked with me that day. Before the hike, he checked in several times to make sure that the route we would be hiking had a number of good “viewpoints,” especially in the steeper sections. On the day of the hike, he arrived with quite a large backpack, which seemed a little odd considering we were doing a half-day hike.
Anyway, once we got near the top of the mountain and took a much-needed break at one of these “viewpoints,” which had a steep drop-off of over 100 meters, he proceeded to sort a few things in his backpack, walked to the edge of the rock face, wished us a nice day, and jumped—much to the surprise of my other guests. We then saw he had pulled his parachute and was lining up to land on a contour path down below. Just such a strange day out whenever I think of it.
Marc Bromhall, Founder, Cape Trek
Overbooked Apartment Leads to Unforgettable Stay
During a scouting trip to Sardinia, Italy, I planned to stay in an apartment in Golfo Aranci for three weeks while preparing for a travel agent FAM trip and exploring a potential seasonal residence for myself. Upon arrival, I discovered the apartment was overbooked and unavailable. Initially amused that such a mishap happened to a travel professional like myself rather than one of my clients, my amusement quickly turned to concern as I faced the prospect of finding immediate accommodation.
The next day, during a site inspection, I shared my predicament with a local hotelier. With a warm sense of humor, she said, “We cannot have you stay in the streets of Sardinia,” and graciously invited me to stay at her property, the Gabbiano Azzurro, for the same rate as the apartment. She went above and beyond, taking care of my food, laundry, tours, and more, turning what could have been a stressful situation into the best trip of my life.
This experience underscored several valuable lessons in travel: always prepare for the unexpected and maintain flexibility. Effective communication is crucial—sharing your situation with local contacts can open up solutions you may not have considered. Always have a backup plan, like additional accommodation options, to save you from potential headaches.
Moreover, leveraging local hospitality can solve logistical problems and enhance your travel experience. Local businesses and hoteliers are often willing to help and can provide invaluable resources and insights. This approach can transform potential disasters into memorable adventures, reminding us that the best travel stories sometimes come from the most unexpected circumstances.
Tammy Levent, President, Elite Travel Management Group, Inc.
Diesel Disaster Turns Into Irish Charm
One of my funniest travel stories happened during a trip to Ireland. At the start of what would have been an amazing day trip exploring the Blarney Stone, I needed to refuel my rental car. Pulling into a small gas station, I grabbed the nozzle and started filling up the tank. It wasn’t until a few minutes later, after the car started shuddering, that I realized I had made a terrible mistake: I put diesel into a gasoline car!
In Ireland, the diesel nozzle fits into a gasoline tank, but not the other way around. Panic set in as I envisioned the potential damage to the car and the ensuing costs. I pulled over and got a tow truck on the phone for help.
The driver was incredibly understanding and even came with a siphon so we could get the diesel out. While waiting for him to arrive, I chatted with some locals at the station, who shared their own funny travel mishaps, making the situation more lighthearted. They assured me that it happens more often than one might think.
When the tow truck arrived, he quickly drained the tank, laughing along with me as he recounted similar stories from other travelers. Though it was a bit of a hassle and cost a few hundred euros, the kindness and humor of the Irish people turned what could have been a stressful ordeal into a memorable and amusing experience.
Now, whenever I think back on my trip to Ireland, I can’t help but laugh at the image of me standing there, bewildered, holding the diesel nozzle, and being rescued by the friendly locals. It was a classic travel mishap that turned into a funny and unforgettable story.
James Edge, CEO, Beyond The States
Accidental Wedding Guest in Singapore
One of my funniest travel stories took place in Singapore. I was exploring the city’s famous Marina Bay Sands area and decided to visit the SkyPark Observation Deck for the stunning panoramic views.
Excitedly, I entered what I thought was the correct elevator, only to realize that I had inadvertently joined a private event lift. I ended up in a swanky ballroom filled with elegantly dressed guests in the middle of a wedding reception.
Dressed in casual tourist attire, I clearly didn’t belong, but before I could sneak out, a friendly older gentleman mistook me for a distant relative and began introducing me to everyone.
The bride and groom were incredibly gracious and found the mix-up amusing, inviting me to stay for a while. We all had a good laugh, and I even enjoyed some delicious wedding cake before finally finding my way to the observation deck. It was an unexpected and hilarious detour that made my trip to Singapore unforgettable.
Aseem Jha, Founder, Legal Consulting Pro
Jet-Lagged ‘Toilet Ninja’ in Japan
One of the funniest travel stories I have happened a few years ago when I visited Japan. I was at the airport, exhausted from the long flight and struggling with a bit of jet lag. I went to the restroom to freshen up, and that’s where things took an unexpected turn. You see, Japanese toilets are quite high-tech, with a multitude of buttons and features. In my groggy state, I pressed what I thought was the flush button, but instead, I activated a bidet function that started spraying water everywhere. I tried to stop it, but in my panic, I only managed to press more buttons, each triggering different functions.
Eventually, a kind airport staff member heard the commotion and came to my rescue, turning off the water and showing me how to properly use the controls. We both laughed about it, and she even jokingly called me a “toilet ninja” for my unintended button-pressing spree. To this day, I can’t think of that incident without chuckling, and it always reminds me to take a deep breath and carefully read instructions, no matter how tired I am.
Gabrielle Yap, Senior Editor & Culinary Entrepreneur, Carnivore Style
Need even more wackiness? Check out some of my favorite quirky Prague statues.
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