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20 Embarrassing Travel Stories That Will Make You Laugh & Blush

Looking for embarrassing travel stories?

Then you’re in the right place!

Recently, I asked some of my favorite travel bloggers to share stories of embarrassing moments from the road.

Get ready to laugh, blush, learn some important lessons, and be reminded that travel isn’t always perfect. In fact, sometimes it can be downright hard.

Additionally, travel can be quite a humbling experience and, in my opinion, is best enjoyed when the traveler removes expectations and rolls with the punches.

Ultimate Travel Planning Kit

Before we dive into the embarrassing funny stories, I want to invite you to grab access to my free Ultimate Travel Planning Resource Library.

The resource library features planning printables, travel quizzes, trip guides, Google Maps, and spreadsheets that make travel planning a lot easier — and even fun!

Grabbed access?

Then let’s dive into the list of embarrassing true stories from the road.

Embarrassing Travel Stories That Will Make You Blush

1. An embarrassing moment on an Italian train

If you enjoy short funny travel stories, you’ll love this.

My now-husband and I were at the end of an Italy road trip, and were dropping off our rental car in Naples, where we would board a train to Milan.

Because Naples is known as the birthplace of pizza, we decided to get some before our departure.

A few locals recommended L’Antica Pizzeria da Michele, so off we went, thinking we could grab a quick slice.

Wrong.

We waited over two hours for a small pie and then had to race for our train. It was our first time taking the train in Naples, too, so we weren’t even positive where the station was.

Luckily we made it, though I was extremely sweaty once we got to our seats. In an attempt to cool down, I went to the bathroom and changed into a dry bra and t-shirt, throwing the drenched clothing in my backpack.

Because we were disorganized from our mad dash, I started rummaging through my backpack and moving items around once I got back to my seat.

I must have been really disoriented, because a few minutes later after I had sat back down the man in the seat behind me tapped me on the shoulder.

“Umm…I believe this is yours.”

It was my sweaty bra and t-shirt, which had somehow fallen into his lap.

Turning bright red, I took the garments, turned around, and stayed silent for the rest of the trip.

Talk about stories of embarrassing moments!

-Jessie Festa from Jessie on a Journey

2. That time I fell into a fountain in Australia

If you love crazy travel stories that are also funny, here is one of my hilarious embarrassing stories from when I studied abroad in Sydney, Australia.

It involves me making a fool of myself in front of my brand new friends and also showing them how terribly uncoordinated I am.

My most embarrassing travel story

I’ve shared the story in video form (above) for a fun twist.

This is one of my favorite short travel stories, and one my friends from study abroad still bring up to this day. Luckily, we laugh about it now!

I’m not going to lie, I momentarily contemplated hopping on a plane back home to New York, as this truly is one of my most embarrassing stories.

-Jessie Festa of Jessie on a Journey

embarrassing funny stories on a tokyo metro
A busy metro in Tokyo, Japan. Photo by Stefan and Sebastien from Nomadic Boys.

3. No touching in Japan

One of my favorite travel experience stories takes place in Japan.

The Japanese are the most polite, civilized, and obliging people we’ve ever met. Everything is done with a sweet smile and a polite bow.

We also noticed that in Japanese culture, personal space is a big deal, as is touching — or should I say, no touching!

Whereas quite a few Western cultures are docile with each other when it comes to general greetings — such as a kiss on the cheek in France and Italy, or a hug or handshake in the USA and UK — in Japan, this is a big fat no!

I learned this the hard way, and it turned out to be one of those funny embarrassing moments in public.

During a packed Tokyo metro journey one morning, I gave up my seat to an elderly Japanese woman who was standing up. She warmly accepted my offer and was very grateful to me — so grateful that she began to perform a series of very dramatic bows to me.

I wanted to tell her it was no big deal and did this by reaching out to pat her shoulder (this was pre-Covid days!).

This would be a natural thing to do back home to someone who had done something sweet to me and I wanted to express gratitude.

But as soon as I did this, the woman’s smile disappeared and the bowing stopped!

She gave me a look of concern, then cringed and briskly took her seat. Honestly, she looked at me like I was some kind of perpetrator but quickly stopped when the confused expression on my face showed that I meant her no harm.

I later learned that in Japan, touching is a big no-no, especially with people you’ve never met.

As such, the traditional form of greeting someone in Japan is to bow to each other with around 1 meter of distance so as to respect personal space. 

In hindsight, I should have reacted to the woman by smiling and bowing back to her.

– Stefan Arestis and Sebastien Chaneac of Nomadic Boys gay travel blog

Real life embarrassing stories in a Las Vegas casino
Chris and her friend had an embarrassing misunderstanding in Las Vegas. Photo by Chris from The Aquarius Traveller.

4. Aussie slang confusion

We were two Aussie travelers experiencing some of the highlights of the USA.

I had been around the block traveling for a few years and knew some of the language variations between the two English-speaking countries.

My friend however, was a bit of a novice when it came to this.

After arriving in the bright shiny city of Las Vegas, we ventured out to explore. A popular choice was watching one of the stage shows available at nearly every casino on the strip.

As I had booked most of our activities before leaving Australia, we were asked to come and collect the tickets for our show earlier in the day.

Now, let me preface what comes next with this:

When it comes to Aussie slang, the best words are the ones that sound like something familiar but mean something completely different.

So when picking up the tickets from the booking clerk, we were trying to understand the signage and dress code suitable for entering the theatre.

My friend then proceeded to ask:

“Can we wear thongs?”

There was a blank stare and a cheeky smirk from the booking guy and I instantly replied to him that my friend wasn’t asking him if she needed to wear “underwear,” but was in fact asking if we could wear flip-flops.

When understanding what he thought she meant, my friend’s face turned bright red. The booking guy then started laughing loudly while saying it was okay to wear that kind of footwear.

It didn’t take my friend long to walk away in embarrassment. There were no more questions to ask after that.

– Chris of The Aquarius Traveller

Stories of embarrassing moments on a Mexico beach
Michele got stuck in some dangerous currents and lost her bikini in the process. Photo by Michele from A Taste for Travel.

5. Naked and afraid in Mexico

If you love funny embarrassing stories, here is when I ended up naked at the beach in Mexico.

I learned the hard way that the beaches in Mexico are not to be trifled with!

I’d been swimming at a local beach on Mexico’s Pacific Coast almost every day without any problems, floating lazily in the waves with the sun on my face and not a care in the world.

Until one particular day everything changed. The water looked much as it always did — there were no red flags flying or other beach warnings — but within minutes I found myself drifting further and further from the beach.

I wasn’t alone, either. Many other people were looking at the shore and attempting to swim in, only to get pummelled in the cresting waves.

Just as I started to really tire of treading water, there appeared to be a lull in the wave action so I decided to make a mad paddle to shore. 

It didn’t take long before I got caught in a breaking wave. It churned me around in the surf like a washing machine then tossed me onto the sand at the water’s edge.

I clawed my way up the sand and away from the incoming waves. Even though my mouth was full of sand and my hair twisted like a corkscrew on top of my head, I was so grateful to be alive. I just lay there on the sand gulping for air and staring at the sun. 

Until I realized that in the turbulent wave action both the top and bottom of my bikini had been ripped off my body and were nowhere to be seen. I was stark naked.

The only saving grace was that the same thing had happened to an elderly man and there were actually two of us in the buff in the sand.

Thank goodness for the kindness of strangers, as some kind onlookers ran over to help and provided us with some towels so we could find our beach umbrellas. I was grateful to be alive but very embarrassed!

– Michele of A Taste for Travel

embarrassing stories in Istanbul Airport
Erin mistook the Prayer Room at Istanbul airport for the bathroom. Photo by Erin from Sol Salute.

6. Sick in Turkey

Unfortunately, I’m all too familiar with throwing up in airports and on planes. I tend to push myself to my limits and on my honeymoon in Turkey, I was no different.

After a week of whirlwind wedding activities, which included chauffeuring a car full of Argentinian in-laws all over Texas, my husband and I boarded a 15-hour flight to Istanbul.

I ignored my mother-in-law’s advice to only take one sleeping pill and popped a second confidently. It had been eight hours since the first; surely, I was fine.

I was not fine.

“Do you see ants?” I remember asking my new husband.

He did! We may have been in bad shape but at least we hallucinated together. Talk about a romantic travel love story!

We landed with zero rest. Did it stop us? Of course not!

Ant hallucinations and exhaustion be damned, we were going to explore Istanbul.

And explore we did. We squeezed every minute out of that 20-hour layover before we found ourselves back at the airport, even more exhausted than before. 

We got into the massive queue to check-in for our flight. Immediately I realized all was not well. I told my husband that I didn’t feel quite right but leaving our spot in this long line was not an option.

“Suck it up, Erin,” I told myself. “It won’t be too long.”

In the meantime, I scoped out the room, searching for the closest bathroom. I saw the iconic sign in the distance, the triangle dress that tells everyone everywhere that there’s a restroom here. I kept my eye on it, my oasis, for the entire wait, plotting my route to salvation. 

A short eternity later the gate agent handed me back my passport.

I was off; power walking to the restroom with everything around me a blur.

Barely making it, I barged in — in the clumsy way that only a loud American in Europe can do — grabbed the closest trash can, and got sick. 

Relief!

That is, until I raised my gaze and felt immediate shame.

I was not in the bathroom at all, but a prayer room!

Devout Muslim women from around the world were knelt down in prayer. I had desecrated their prayer room.

Mumbling apologies I can only hope they understood I slinked out of the room vowing never to exhaust myself in such a way ever again.

– Erin of Sol Salute

embarrassing true stories in Athens
Fuad needed a desperate trip to the bathroom in Athens. Photo by Fuad from A Walk in the World.

7. When nature calls in Greece

I had just landed in Athens from Santorini. Before leaving Athens for my next destination, I had about nine hours to kill.

As I was backpacking, I did not want to go to a hotel. Instead, I planned to explore Athens on foot.

I had a heavy backpack with me, though even so, I was happy to see the ruins and architecture of Athens.

It was a warm day, but I tried not to drink too much water to avoid needing the bathroom.

After five hours of walking, I could not resist any further. I was both hungry and thirsty.

I did not have much money left as I was approaching the end of the Euro trip; however, I entered a restaurant and ordered some food. I don’t know how many bottles of free tap water I drank, but it was the tastiest water I ever had!

When I left the restaurant, I had about three more hours to catch a flight.

Before going to the airport, I wanted to have one last look at Athens.

All was going well, until about 30 minutes later when I felt immense pressure in my bladder.

I knew at that very moment that I couldn’t wait until I got to the airport. Thinking back to how much water I’d drank at the restaurant, I wanted to kick myself — though instead started looking for a toilet.

I was in a place surrounded by historic buildings, so I was sure that I could find a toilet inside of any of them; however, after storming into one of them I found that it was closed.

Time was running out.

I could not think straight. The Greek letters listed everywhere only made me more puzzled. I searched for a place on Google Maps, but no luck.

Then I saw a large green park; the National Garden.

Entering it, I knew it was not right, however; I didn’t have any alternative. All that I needed was a dark, quiet place.

Luck was not on my side that day; the garden was well lit with plenty of people jogging.

I didn’t care.

I unzipped, and stood in the middle of the garden, with shouts of disbelief around me making my ears warm and red with embarrassment.

But the only thing that mattered at that moment was the heavenly pleasure I felt in those 30 seconds (yes, you read it right; it was more than a liter, I guess!).

I ran away as fast as I could afterward! 

– Fuad of A Walk in the World

embarrassing moment stories in a California porn studio
Carol accidentally ended up on a porn film set. Photo by Carol from California Crossings.

8. That time I ended up in a porn studio

I normally organize my own adventures and am not great at paying attention when other people are in charge.

So, it’s no wonder that I accidentally ended up on a porn studio tour.

I blame Alvin.

You see, Alvin runs an urbex photography group that I’m a member of.

We go out and shoot things like tunnels, ghost towns, and abandoned buildings. For such a pretty city, you’ll be surprised to know that there are quite a few places like that in San Francisco.

Alvin arranged a shoot in San Francisco’s Mission District, which included a visit to the historic Mission Dolores cemetery, an outside art studio, and The Armory.

When Alvin described The Armory, here’s what I registered:

A historic military building that was used as an arsenal during WWI. The building is cool because remnants of the now-covered Mission Creek rise up from the ground and flow through a channel in the basement.

Here’s what I didn’t register:

At the time of our tour, The Armory was owned by a porn magnate and was used as a film studio and S&M event venue.

My friend who had previously done the same tour swears that she told me, but all I heard was blah blah cemetery blah blah creek in basement.

I showed up on the appointed night to learn that our tour guide specialized in a very particular kind of Japanese rope bondage and that she was sponsored by a rope company from Texas that also supplied rodeos.

I also learned what BDSM stands for — prior to the illuminating tour, I had only heard of the S and M parts.

Additionally, I learned that robots can be configured with very insistent motorized prosthetic devices.

And also, that the studio provided worker’s compensation insurance and deployed a sophisticated database that housed all of their freelance talent, tagged by skill.

The creek in the basement was pretty cool, too.

– Carol of California Crossings

most embarrassing stories in Southeast Asia
Bailey fell out of bed in the middle of the night and woke up the entire room. Photo by Bailey from Destinationless Travel.

9. Getting a bit too drunk in Cambodia

On my first ever backpacking trip I went to Southeast Asia.

Just like most budget backpackers, I loved to have a few drinks in the evening — especially when they were cheap! 

However, when I visited the island of Koh Rong in Cambodia, that’s when the cheap drinks didn’t work out so well for me.  

Koh Rong is the perfect place for backpackers who want to party.

This tiny sandy island is full of bars and lively hostels. I managed to pick up a 750 ml bottle of rum for only $1 USD and I was thrilled! After a big day in the sun, I was going to really enjoy some rum, and that’s exactly what I did.

My sister, boyfriend, and I all went to a friend’s hostel that night.

Long story short, I ended up drinking nearly the entire bottle of rum all to myself! I don’t remember getting back to our hostel, but my boyfriend tells me he had to pretty much carry me there and lift me into bed.  

I was staying in a dormitory room and had the top bunk. As with many hostels, my bunk bed didn’t have a railing. Me, in my drunken passed-out slumber, actually rolled off the bed in my sleep! 

Thump!  

I hit the concrete floor hard and woke up startled only after feeling the pain, which is when I also began screaming.

I’d pretty much belly-flopped onto the floor. The thump was very loud and so were my screams and drunken cries. 

Besides my body being bruised, my ego was, too.

I woke up the entire 10-bed dorm room and strangers were actually laughing at me. Talk about a travel fail!

Needless to say, I got made fun of by other travelers for the duration of my stay in Koh Rong, and my sister and boyfriend still bring it up today.

I did learn a lesson, though:

Never sleep on the top bunk without a railing, especially if you’ll be drinking rum!

– Bailey of Destinationless Travel

10. An embarrassing bathroom moment on a coach

It was a sunny summer morning, and I was super excited to finally take my mom to explore London. I was a student and lived in the southeast of England.

We woke up early and headed to the bus station to get onto the two-hour coach to London. We sat at the front of the bus, and straight away I regretted eating that dodgy fish the night prior.

My stomach was cramping, and the feeling of needing the toilet was building up. The coach was already on the motorway with no scheduled stops until London.

You know that feeling when the physiological need is so strong you know you won’t be able to ignore it, and you must go?

Well, that’s how bad it was.

Luckily, the coach had a toilet, so my mom suggested I use it. I really had no other option, so I went.

The cubicle was tiny, and it was not easy to use the toilet inside a moving bus. When I got out and walked back to my seat, I noticed everyone was covering their faces and either looking away or giving me a disgusted glance.

When I got back to my seat, my mom told me the whole bus received the “toilet waft” through the air conditioning.

I was so embarrassed I wanted to disappear, and my amused mother could not stop giggling. She still brings the story up on family gatherings. 

– Mal from Raw Mal Roams

crazy travel stories on an airplane
Jenny of Traveling Part Of 4 sitting by a firepit

11. Flash flight

The year was 1999, and my significant other suggested we ring in the Millennium in Hawaii.

On our final day in Hawaii, we planned a trip from Oahu to Maui. We leisurely drove the Road to Hana, keeping track of the time to get to our reservation at the fancy restaurant for dinner and making the last flight out back to Oahu.

In typical fashion, we were running late. I rushed to change into my super cute summer dress and strappy sandals that I bought specifically for this occasion.

And we barely made it on time for the reservation!

After scarfing down dinner and dessert, we headed to the airport for the last flight out with no time to spare. We swiftly returned our rental car and then sprinted to the gate.

Of course, we were easily 10 minutes too late for the last flight out. We rushed anyways to the gate to see if, by chance, we could make it. After running by a line of people about 30 deep to our empty appearing gate, we asked frantically, “Can we still board?”

She replied that our gate had changed to that one, as she pointed to the gate with the line.

Whew! We made it.

At this point, I was extremely embarrassed, though my S.O. — who was trying to calm me down — didn’t really know why.

After we boarded and settled in, I confessed that my cute little summer dress had tucked up under my backpack while running to the empty gate.

He says, “So what? They saw your underwear. Whatever.”

That was the kicker.

When we rushed to change to get to the restaurant on time, I could not find my underwear! My derriere was in full effect for the entire line waiting to board the flight.

I will be forever grateful (and mortified) for the multiple beers sent my way during that flight. I guess they won’t forget it either.

-Jennifer Bhatia of Traveling Party Of Four

Embarrassing Travel Stories ice skating
Adrienne’s family on the rink where the awkward travel incident occurred

12. Queen of the ice

My family and I were on a cruise vacation when my husband, my daughter (who was 14 years old at the time), and I decided to try out the onboard ice skating rink on one of the sea days.

I grew up in Minnesota — though hadn’t ice skated in years — and my family had never ice skated before, which made me the most experienced in the group.

As we were going around the rink, I decided to go backward to look at them and help guide them on their skates.

Big mistake.

As I was turning, I stumbled and fell, banging my head on the ice rink wall.

Even though I was wearing a helmet, I still ended up with a concussion and barely remember the next three days of our trip!

-Adrienne Bibb of Addy and Terry

funny travel stories on an airplane in the sky
Nisha thought her plane was about to collide with another plane. Photo by Nisha and Vasu from Lemonicks.

13. When planes almost collide

My embarrassing story happened in the air!

After an extremely hectic week of back-to-back travel, I was terribly tired and all I wanted was a comfortable bed to crash into.

But here I was, standing in a long immigration queue on my way to another destination. By the time I cleared every hurdle including waiting to board my flight, I could hardly keep my eyes open.

I fell fast asleep on the plane as soon as I put on my seat belt — even before the doors were closed. The flight was in the evening and as usual, I had my window seat.

After dozing off for a few hours, I suddenly woke up to some announcements made by the captain. Probably we were passing through turbulence. It was night time and most of the passengers were fast asleep.

With groggy eyes, I looked out of the window and was horrified!

I saw a small plane flying parallel to ours. The plane was neither slowing down nor changing its direction — it was as if it was participating in a race with us.

At that moment I thought the two planes were quickly going to collide. Seriously, this was quickly becoming one of my most dangerous travel stories!

I also thought it was my duty to inform the captain. Perhaps he hadn’t noticed that this tiny plane was so close to ours! I shook my sleeping co-passenger to let me out and called the air-hostess, too.

When I told them the situation, my co-passenger leaned over my seat to look out. And then he laughed out loud. I seriously thought he had lost his mind.

What I was told next made me go very red in the cheeks:

It was actually the wing of our airplane and not another plane. I wanted to vanish from the scene.

Moral of the story:

Sleep well before taking a flight.

– Nisha & Vasu of Lemonicks

craziest travel stories in Myanmar
Adriana had a laundry faux pas in Myanmar. Photo by Adriana from Czech the World.

14. The unexpected power of women’s panties

One day, during our backpacking trip in Myanmar, we decided to go to quite a distant and non-touristy area in Rakhine State to visit the beautiful temple town of Mrauk U.

When we arrived at our accommodation, a kind elderly lady greeted us. She spoke just a few words in English.

Noticing that there was a washing machine for guests at the reception, we decided it was time to do laundry. We brought a bag with our clothes and the woman pointed to her husband and told us that he would take it.

And then it happened.

The man and woman started a very loud Burmese conversation. We didn’t understand a word.

Her husband threw the laundry bag back to us. And the angry woman started pointing to us, first to my boyfriend and later to me, but we still didn’t understand the situation, so we just took our clothes and went back to the room.

Well, we were surprised and also very curious about what had happened, so we did a few Google searches and immediately discovered the reason:

Burmese people are very superstitious and believe that a man can’t touch a woman’s underwear because this will “sap them of their power.”

So the poor lady thought we wanted to hurt her husband!

– Adriana of Czech the World

travel writer and photographer had an embarrassing moment in Zambia
Campbell got fined for public indecency in Zambia. Photo by Campbell from Stingy Nomads.

15. Getting fined for public indecency

While traveling Africa along the east coast, I made friends with the crew and passengers on an overland truck at a campsite in Malawi. The group was on a tour through several African countries.

Everyone on the truck agreed it was okay for me to get a ride with them from Malawi to Zambia.

It was a hot day and I drank a lot of water on the way. We arrived on the border with Zambia after a long day of driving, which is when I urgently started looking around for a toilet.

It was not much of a border post and I headed for a tree not far away on this barren landscape, thinking it was far enough away, and that nobody would really spot me behind the tree.

Unfortunately, I was very wrong and the Zambian police took “public indecency” in the middle of nowhere very seriously.

On the way back I was met by an officer with a gun who took me to his superior. He told me that I broke the law, it was seen as a serious offense, and that he was going to charge me with public indecency.

Ultimately, I was issued a fine — that I had to go and pay at the magistrate’s office in the nearby town.

It was an uncomfortable situation since I was not even a paying client on the tour I was hitching a ride with. I was very grateful that the tour leader did not just leave me there and that the truck took me to pay the fine with a police escort.

Overall, I was quite embarrassed that the guests had to drive the detour to town and wait for me in the truck on an extremely hot day while I paid the penalty at the government office.

– Campbell of Stingy Nomads

16. A massage in Cambodia

Angkor Wat in Cambodia is undoubtedly one of the world’s most iconic
destinations and deservedly a bucket list item for many.

However, my overriding memory of our fabulous day exploring Angkor Wat is unfortunately not the sunrise reflecting in the lily pond but a
massage, a pair of pajamas at least three sizes too small, and an
unwelcome appearance.

Following our incredible Angkor Wat tour, the complimentary massage from our hotel would be just what we needed.

Two young local women greeted my wife and me and provided us with the
garments we needed to change into.

My wife went to the sole changing room so I stayed in the massage room and disrobed.

As I removed the garments from their packaging it was clear that the extra-large I’d requested to cover my 6’2″ frame was far too small.

Somehow I managed to squeeze myself into the three quarter length linen trousers and decided not to breathe deeply for the next 45 minutes.

As I bent over to place my clothes neatly in the corner, the door to the
room opened, and in walked the two massage therapists and my wife. This noise and their greetings covering the unmistakable sounds of ripping cloth from my crotch area.

Believing this could not be too bad I laid down on my front next to my wife as instructed and started to relax as the oils were applied and the massage began.

I remained very conscious of the rip but thought if I stayed in that
position there wouldn’t be any issues. Unfortunately it was only a couple of
minutes before I was asked to roll over and move into a variety of
new positions.

Almost immediately both therapists started whispering and sniggering — with my wife completely unaware of my predicament and the difficult situation unfolding.

The massage finished with a vigorous neck and head massage, so the
therapist asked me to sit with my head down between my legs. As I moved into position the cause of the laughter was literally swinging beneath me.
I was gobsmacked and clueless as to how to react.

Suffice to say I tipped rather generously that day and was incredibly relieved that my wife found the funny side when I answered her question as to why I thought they were laughing throughout the massage.

On our various travels through Asia I’ve always been careful to ensure
we follow traditions and not mistakenly cause offence.

Well, that afternoon I completely ruined years of hard work!

– Paul of The Two That Do

embarrassing stories funny in Cape Town
Rai had her clothes stolen by baboons. Photo by Rai from A Rai of Light.

17. That time my clothes were stolen by baboons

I spent the summer of 2018 in Cape Town, well-known as one of the most beautiful cities in the world. It’s famed not only for its natural setting and dramatic coastline but also for the wildlife living in the surrounding region.

Little did I know I would be having a very close encounter with one of its most visible and intriguing animals, the chacma baboons, on a day out at the beach. 

The city’s good weather year-round makes it a popular destination for beach lovers.

It was almost midday when the African sun is at its peak, so I decided to go for a swim, leaving everything behind and wrapping myself in a towel on the beach.

The waters along the Cape Coast are some of the coldest and I couldn’t have been away for more than 10 minutes before noticing a group of these baboons grabbling through my belongings.

A quick dash towards them and they scattered — though unfortunately they did not leave much behind. My clothes were missing and those that remained were left tattered.

The good news:

The baboons hadn’t shown much interest in my wallet, but I was forced to spend the rest of the day — including my way back home on public transportation — in nothing but short swim trunks and an embarrassed smile. 

Following the incident, I heard that the baboons of Cape Point are the only ones in their species that mine the beaches for seafood. And being protected under environmental law, they have become brazen in their attempts, raiding houses and belongings, and even mugging people.

Lesson learned.

– Rai of A Rai of Light

embarrassing true stories on a plane
The next of our embarrassing true stories takes place on a plane. Photo: Kelly via Pexels.

18. Lost menstrual cup

One of the unglamorous things female travelers have to think about is our menstrual cycle. It is not a fun topic, but it is our reality.

Over the last few years, I made the decision to switch to more eco-friendly sustainable options that do not involve plastic.

This particular story starts with my family’s big move to Mexico, during the pandemic.

My cycle decided to show up two days before the big move, so that was fun. I headed to the airport confident in my menstrual cup because it hadn’t failed me in several months.

While on the flight I had to remove the cup and couldn’t get it back in. The passengers could hear me rattling and moving things around in the lavatory, as I tried to get the menstrual cup inserted.

After almost 10 minutes I gave up and decided to return back up to my seat, and use my back-up protection.

When I exited the lavatory, I could see everyone staring at me, wondering why there was so much commotion.

After sitting down I realized I didn’t have my menstrual cup. The first thought that came to mind was that I accidentally flushed the cup.

I started to panic. Did I drop it on my way back to my seat? What if someone finds it?

After 15 minutes, I returned to the lavatory to see if my cup was on the floor.

Finally, it hit me. I went through the trash in the lavatory and found my menstrual cup. I was so relieved to find it still wrapped in the paper towel.

Although it is funny now, at the time I was freaking out.

– Corritta from My Eco Flow

stories of embarrassing moments in Las Vegas
One of the funny embarrassing short stories is from Kay. She dropped her underwear on a busy Las Vegas street. Photo by Kay from The Awkward Traveller.

19. Dropping my underwear in Vegas

Before I get into the nitty-gritty of how, one faithful hot and sweaty August day, I displayed my panties to the world, there are a few details you need to know.

The last time I had been to Vegas, in 2015, all of the hotels on The Strip had free parking. Fast forward to 2017, I had flown to Vegas for a quick and cheap weekend trip.

My Vegas crew got me free entrance and drinks to the day club at MGM Grand, so after I landed, I hopped in my rental car and drove to the hotel.

Only to find out that parking at the MGM Grand was now paid.

And expensive.

So, in the name of being a budget queen, I drove to the very far away Venetian Hotel because they were one of the only hotels left with free parking.

But that left me with another problem:

I was now going to be late for the party. 

Free entry — but most importantly free drinks — was only available for a limited time, and I now had only 45 minutes to get down The Strip and into the pool of the MGM Grand if I wanted to secure my free wristband.

I quickly changed into my swimsuit in the car, throwing a dress on top and a change of clothes — aka what I had been wearing on the plane — in my mini backpack as I dashed out of the parking lot.

Practically jogging down the strip in the blazing summer sun, I shuffled around in my backpack for my sunscreen. After half-hazardly sloshing it over my arms, face, and parts of my leg — I had to do a little hop to get my ankles as I walked — I slung my backpack to the side to plop the sunscreen back in.

A few seconds later, someone tapped me on the shoulder:

“Um, Miss…”

I turned around and spotted what everyone was now looking at. A lump of colorful (worn) underwear.

My worn underwear.

Just as I was about to pretend I had never in my life seen that panda MeUndies print before, the person who tapped me added, loudly, “It fell out of your backpack.”

I snatched up my underwear and ran into the nearest hotel lobby. I never made it to the pool party.

– Kay from The Awkward Traveller

embarrassing true stories in Hong Kong
Lotte had an embarrassing misadventure in Hong Kong. Photo by Lotte from Beste voor Kids.

20. The locked hotel room in Hong Kong

One of my most embarrassing travel moments was the time when I was locked out of my room in Hong Kong during Chinese New Year.

After a long flight from Auckland, New Zealand, I was exhausted and just wanted to get to my hostel as soon as possible.

Because it was Chinese New Year, I had already booked a room as I didn’t want to run the risk of ending up on the street because everything was full. I had booked a room in one of the countless hostels in the Chungking Mansions complex.

That was a mistake. A big mistake. Don’t go there. Ever! 

It’s a maze — and not in a fun way. My husband and I walked around for an hour after we finally managed to find what was supposed to be our room; however, when we arrived, there was nobody there.

So I called the number scribbled on a piece of paper pasted on the door and was told my reservation was canceled.

Just like that.

There I was, on Chinese New Year, bone-tired and without a place to stay. 

But wait, it gets worse… 

Out of thin air, a guy emerged and told me he had a room for me. As dodgy as I found this, I was too tired to care so I went with him.

He showed me the room and I quickly agreed. So far so good.

But then I made the monumental mistake of leaving the room to see the parade — because I couldn’t justify being in Hong Kong during Chinese New Year and not watching the parade that passed in front of Chungking Mansions.

I mean, this was a once in a lifetime opportunity!

Tired as I was, I pulled myself together and went to see the parade. That was the only fun part of this disastrous night.  

When I got back to my room and put the key in the lock nothing happened. I pushed and wriggled and cursed and tried and finally burst out in tears because I couldn’t get the door to open.

Luckily the people in the adjourning room came to check out the noise of me trying to break down the door and gave me the number of the guy who had shown me to the room.

So, I called him and after an hour he finally arrived and opened the door. Needless to say, I changed hotels the next day. 

– Lotte from Gezond Weekmenu

Bonus Short Travel Stories

Looking for more short stories about traveling the world? Check out:

25 Crazy Travel Stories You Need To Read To Believe

23 Inspiring Travel Stories Sharing The Kindness Of Strangers

16 Short Funny Travel Stories That Will Make You Laugh Out Loud

38 Inspiring Travel Love Stories From The Road

17 True Short Adventure Travel Stories To Inspire Your Next Trip

Sexual Assault Stories From The Road (& What I’ve Learned)

8 Crazy NYC Subway Stories That Will Make You Hail A Cab

A Host’s Perspective: My Worst Airbnb Horror Stories

21 Travel Horror Stories About Scary Travel Experiences

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About Jessie Festa

Jessie Festa is an New York-based travel content creator who is passionate about empowering her audience to experience new places and live a life of adventure. She is the founder of the solo female travel blog, Jessie on a Journey, and is editor-in-chief of Epicure & Culture, an online conscious tourism magazine. Along with writing, Jessie is a professional photographer and is the owner of NYC Photo Journeys, which offers New York photo tours, photo shoots, and wedding photography. Her work has appeared in publications like USA Today, CNN, Business Insider, Thrillist, and WestJet Magazine.

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Hi, I’m Jessie on a journey!

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7 Comments

  1. Krista on at 6:52 pm

    I loved reading these stories! I always have at least one embarrassing story from my travels so I’m glad I’m not alone!

  2. CJ on at 9:18 am

    What a crazy collection of stories! I would be so mortified to wind up naked on a public beach!

  3. SNK Social Fame on at 7:46 am

    Such a good post! Thanks for sharing. Really very useful and informative post.

  4. Slope Unblocked on at 12:03 am

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  5. Candy Crush on at 4:19 am

    I’m a conscious solo traveler on a mission to take you beyond the guidebook to inspire you to live your best life through travel.

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