The 9 Travel Moments I’m Least Proud Of

The 9 Travel Moments I'm Least Proud Of


Cue expressions of shock and gasps of horror, but I’ve got news for you people, travelling isn’t all what it’s cracked up to be!

Yes, there are moments of picture-perfect sunsets over paradisiacal beaches and love affairs with exotic strangers that sweep you off your feet.

However, there’s also times when you’ll find yourself with your head in a toilet bowl (literal and metaphorically) gagging on your cringe-worthy behaviour in a bathroom ridden with cockroaches.

So yes, travelling isn’t always what it’s cracked up to be!

And guess what, no matter how long you travel for, or how adept at traversing the world you might think you are, the occurrence of those travel moments you’d rather forget, doesn’t suddenly stop.

Almost as if the universe was giving you a serious ego-stripping in fact, the more arrogant you seem in your approach to travelling, the more regularly those awful moments seem to occur!

Or maybe that’s just me!

Anyway in lieu of celebrating the bad and the ugly of travel, as much as the good (or in order to transform the bad and the ugly into good valuable lessons!), here are 9 travel moments I’m least proud of.

Related Posts

This page contains affiliate links meaning Big World Small Pockets may receive a small commission on any purchases at no extra cost to you.

#1 Drinking on the Street, Italy

Slovakia, Bratislava, Craft Beer Bar

So let’s start at the beginning.

I’m 18 and on my first backpacking trip in Italy with my best friend.

True to form, or at least what was considered “normal” behaviour for British teenagers, we began our night’s drinking in our hostel.

Well on our way when the hostel ‘quiet time’ came, we decided to take our antics onto the streets – again a very normal behaviour for where we were from.

Finding a bench and acting all silly with our booze bottles, we were having a great old time laughing like crazy until a group of Italian kids arrived on the scene.

Turns out drinking on the street is/was not quite as acceptable in Italy as in the UK!

Very soon, we were surrounded by a group of 10-15 year olds, all intent on mocking us and impersonating us as a couple of drunk old tramps.

Well very quickly our laughter turned to silence and our bottles remained untouched in our hands.

After a while, there was nothing for it, but to silently extract ourselves from the situation and creep back to the hostel – shamed into doing so by a group of young kids!


Download Your FREE eBooklet
5 Great Reasons to Work & Travel + Tips

Just enter your details below and I'll email it you - simple!

Information will be sent to the email provided above


#2 Getting Off at the Wrong Stop, South Africa

South Africa, Kruger National Park, Tree Branches

What I did tell you about the universe slapping you down?

Well after Italy came South Africa and now 19, thought I was quite the worldly traveller, proficient at looking after myself wherever on the planet I might end up.

While it turns out that wasn’t quite true, as I was soon to find out.

Intent on using the township taxis rather than Greyhound buses in South Africa, I always prided myself on navigating their complex systems, changes, stations and stops – despite the warnings of the hostel where I was staying to avoid them.

Not interested in listening to their advice however, I took off to Durban for a few days, returning, as I’d got there, via township taxi.

However in the final stretch of the journey, after 4 separate buses and with night falling, I finally came unstuck!

Positive I was approaching the stop for my hostel, I called out to the driver to let me off the bus and hopped out into the darkness as it pulled away.

Only then did I realise I was actually standing in the middle of nowhere, on the side of the highway, with no visible signs of civilisation around me. I was definitely not near the hostel.

Luckily after walking along the street for only a few minutes I did come across a payphone and, hanging my head in shame, called the hostel to tell them what had happened.

Thankfully they didn’t rub in their advice in too much and amazingly came out into the night to look for me, as I had no way of describing to them where I was!

Boy was I glad to make it safely back into my dorm bed that night!


#3 Almost Sinking on a Boat, Mozambique

Mozambique, Bazaruto Archipelago, Local Boat

After South Africa came Mozambique and there my friend and I met 2 guys who were sailing on a boat all the way to the Seychelles and looking for crew.

Without much further investigation, we immediately volunteered.

Unfortunately, this may have been influenced by that fact that at least at one these sailors was incredibly handsome!

And so, only a few days later, we found ourselves without any sailing experience, navigating the Mozambique Channel – one of the busiest shipping channels in the world – on a 20ft catamaran.

Was there any sort of GPS system on board?

Was there any sort of weather forecasting equipment present?

Was there are any sort safety raft or vessel at our disposal?

The answer to all of these questions, we found out, was no.

Which became evident very quickly when we encountered a massive storm.

Turns out the above are definitely all questions you should find out in advance before getting on a catamaran with a couple of strangers, because as soon as you have water entering the boat, the captain passing out with exhaustion on the deck, all the boat batteries smashing onto the floor and you’re floating through the darkness without being able to contact the passing ships that might plough into you at any moment, it’s good to know these things.

Miraculously we got out of the storm, but going into that travel experience so wide-eyed, naive and yes, lustful, is definitely something I’m not so proud!


#4 Getting Caught in a Dorm Bed, Nicaragua

Israel, Tel Aviv, Abraham Hostel Private Room

Enough said!

If you’re confused, read my post about the 10 worst people you can meet in a hostel!

Yes, I have been one of them.


#5 Drunken Hitchhiking, Mexico

Indonesia, Bukittinggi, Road

Crashing twice in 2 separate vehicles, with 2 separate drivers, both drunk, within 5 minutes of each other, on a road in Mexico, is definitely one of the travel moments I’m least proud of!

Being so “laid back” that I missed the bus, the simple solution was to hitchhike back to where I was staying

Also being so “laid back”, it didn’t matter that the drivers that picked me up, seemed to be a bit tipsy!

It didn’t even seem to matter that one of them was hanging out the driver’s window with a beer in hand!

After the first hitchhike ride ended up with us driving into a tree, what were the chances of me then getting another lift and it then also crashing (this time by flipping the car and sliding down a bank) all in under 5 minutes?

On a Sunday afternoon, in southern Mexico, when drunk drivers are involved, it would seem quite high!

Thank goodness my survival rate that day was also high and I came out unscathed (albeit a little shaken) twice!


#6 Missing Out on a Volcano, Guatemala

Ethiopia, Danakil, Volcano Fire

I used to have this whole thing about not doing or seeing the main or most popular attractions in places.

Call it my perpetual need to be a bit different, or call it my resistance to organised fun, but I spent many years of travelling going to countries, only to forego their most frequented landmarks.

After 3 weeks in Cape Town for example, I never climbed Table Mountain. After multiple times in Paris, I never went to the Eiffel Tower.

And after 3 months in Guatemala, I never climbed a volcano!

Thankfully I’ve got over this need to be different now and realise that many of the most famous attractions in a country are popular precisely because they are excellent.

During my time in Guatemala however, this rather shameful arrogance was still entrenched in me. And so, despite my love of nature, hiking and camping, I never climbed a volcano in this most famous tectonic land – certainly one travel moment I’m not proud of.


#7 Ending Up With My Head in a Toilet, New Zealand

Thailand, Chiang Mai, Thunder Bird Hostel Bathroom

We’ve all been there.

Those times when one too many drinks catches up on us rather quickly.

Sadly, there have been more than a few times in my case. And it’s never a good look.

Especially when you’re trying to impress a boy.

As a solo female traveller, it’s probably not that safe of a state to get yourself into either.

But if you want to ruin your whole next day of kayaking, it’s a great way to go!


#8 Budgeting for Altitude Sickness, Ecuador

Ecuador, Cotopaxi, Snowy

And it’s not only drinking too much that amounts to a serious case of vomiting as one of the travel moments I’m least proud of.

No altitude sickness did the very same thing!

And before you say, “You can’t help altitude sickness”.

Let me tell you, I probably could have.

One good way to have found out, would have been to have paid for a dorm bed in a hostel situated at 3500m above sea level, rather than being too much of a tight ass and sticking rigidly to the notion I was going to camp there instead.

Camp in a tropical 1 season tent I might add. At 3500m above sea level.

So freezing was I for the entire night that I didn’t end up sleeping a wink.

Despite wearing everything I own, I still spent the night shivering under my sleeping bag and wondering why I hadn’t coughed up the now very reasonable sounding $15 for a bed in a cosy hut!

And no doubt this lack of sleep, contributed to me getting altitude sickness at only 3800m, so much so that I was unable to even attempt the walk up to 5000m that had been the whole reason for the excursion in the first place.

Instead, I could only grab a quick, and awful-looking, shot of the scene, before crawling into some sort of Ecuadorian lodge/restaurant at the side of the road, where I promptly passed out in front of their fire and didn’t wake up until my fellow walkers passed me on their return.

Lesson learnt.

Don’t be so tight!


#9 Not Realising I was Being Robbed, Colombia

Colombia, Coffee Region, Views

Despite having been living and studying Spanish for almost 2 years in Latin America, when the words “Manos Arriba!” reached my ears one night in a dark alley in Colombia, I had to turn to my friend and ask him what the 2 men were saying to us.

They saying “Hands in the air … we’re being robbed!”, he hissed back.

“Oh right, yeah”

I blame the rapid pace of the situation for my lack of understanding, but nevertheless the whole was pretty embarrassing.

First, the act of being robbed in a place I’d been living for 3 months and bragging to my friend about how safe I felt – it was his first night in town – was pretty awful.

And then, of course, the act of not realising we were being robbed was pretty bad too!

Third was the fact that for some reason I’d stepped out that evening with my entire wallet on me and my passport.

Dumb. I know.

And highly embarrassing.

Saving grace however, was that despite patting me down, my attackers failed to find any of these possessions stuffed in the front pocket of my hoodie.

Embarrassing for them!




So there you have it, confessions are in, the 9 travel moments I’m least proud of!

What are you embarrassing travel stories … and can they compete with mine?!

I’d love to hear them!


14 thoughts on “The 9 Travel Moments I’m Least Proud Of

  1. Mri says:

    I love the Mexico one. Though got to ask, were you drunk as well? Getting into all of those crashing cars and still keeping your chill. haha.

    As for one some of my worst travel stories:
    1. ‘Almost’ lost my leg due to enjoying a party. I use air quotes cuz it didn’t seem that bad minus the whole not being able to take my weight anymore due to infection (and I have a seriously high pain tolerance). Also only a nurse mentioned that outcome and not the doctor so who knows; either way, still have it!
    2. Getting £10,000 of gear stolen after going on a fantastic hike. More than likely this wouldn’t have happened if we turned around at the end instead of throwing another 20km onto the 9km hike out of stubborn refusal to turn back (the bridges and old path were washed out). If we had done that we wouldn’t have gotten back after dark… Oh, and then this happened afterwards:

    3. Hitching a ride with a creep when my medical problems pretty much incapacitated me. But that’s what pretend sleep is for isn’t it? Except, maybe don’t open your eyes when you hear weird noises… As weird as this might sound out of context, I’m so happy all he did was touch himself.

    • Steph says:

      Sadly was not drunk as well during the Mexico incident – does this make it even more shameful?! Love your stories too, thanks for sharing them. Blimey sounds like you’ve had some real adventures!!! Glad we’re both still here to tell the tales!

  2. Laura says:

    Oh drinking while travelling…it’s fun but often a bad idea. I’ve done some pretty stupid things after having a few too many drinks. I once drove an auto-rickshaw through very busy Indian traffic (As in, I was the driver. Oh did I mention I don’t even have a drivers licence? Don’t ask me why the tuk tuk driver let me drive his vehicle!) At least I can say I was young and stupid haha. I like to believe I don’t do so many silly things nowadays.

    Loved this list. I feel like I can relate to a lot of these. Especially the one about getting off at the wrong stop in SA. Done that!

  3. Gemma says:

    I am so impressed you managed to survive all those experiences!! Especially the Mexican one…so funny. I love hearing about when things go wrong during travels.

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.