Avoiding Travel Mistakes: Lessons Learnt the Hard Way
In the early years of my travel life, I used to think mistakes were something you could avoid with enough research. I packed light, checked in early, did my research, and still – somewhere between the flight gate and the hotel lobby – I’d manage to do something completely ridiculous.
Like exchanging cash at an airport kiosk and immediately realising the damage. Or ordering a hot pot in Mandarin with so much confidence that I was rewarded not with admiration – but with a bowl full of chicken feet.
To be fair, I’ve been lucky in some ways. I’ve never had a flight cancelled, lost luggage, or come down with a stomach bug mid-trip. But I’ve absolutely embarrassed myself in restaurants, underestimated cultural norms, and watched someone’s travel plans fall apart at the boarding gate because their passport didn’t meet the six-month rule.
The thing is, these stories pile up whether you plan for them or not. They become part of the journey. Some you laugh about, some you learn from, and a few – well, you’ll just never do that again.
In this post, I’ve gathered the mistakes I’ve made, witnessed, or narrowly avoided – not to make you paranoid, but to help you travel a little more lightly, both in luggage and in spirit.
Common Travel Mistakes
1. Overlooking entry requirements
A friend’s mum once made it all the way to the check-in counter, bags packed and heart set on vacation with her daughters – only to be denied boarding. Her passport had less than six months left on it.
It's the kind of thing you never think will happen to you, until it almost does. Or does. And the worst part? No one will bend the rules. Not the airline staff. Not immigration. Not even when you cry.
Some of the most common trip-killers:
A passport with under 6 months of validity
Missing entry stamps in certain regions
A visa you didn’t know you needed
These rules don’t care about your intentions or how long you’ve been planning your dream trip. They just don’t. Check, double-check, and ask questions before you go. They’re not out to get you, but they will stop you.
2. Underplanning or neglecting to sort out trip details
There’s a certain romance to landing in a new country with nothing but a backpack and a sense of wonder. But there’s also the very real moment of standing in a bus terminal at midnight, hungry, tired, and Googling “cheap hostel safe???”
It’s not inspiring. It’s just exhausting.
Winging it can work – if you’ve got enough local language, mobile data, and energy to solve problems as they come. But even then, it helps to have just enough of a plan. A map pinned. A screenshot of your hostel booking. A note with the address in the local script.
Some lightweight tools to keep:
Offline Google Maps with saved pins
Pre-downloaded transport apps
A shortlist of neighbourhoods you actually want to stay in
Planning doesn’t kill spontaneity. It keeps you from crying in public.
3. Overplanning or creating an ambitious itinerary
On the flip side, I’ve seen itineraries that pack museums, hikes, and street food crawls into a single afternoon. They’re less "dream vacation," more "corporate team-building exercise".
It’s easy to fall into this trap. Especially if you’re visiting a place you may never return to. You want to make the most of it. But the irony is: the more you cram in, the less you actually experience.
There’s no time to get lost. No room to sit in a park with your thoughts. No chance to linger at a café that just feels right.
A better rhythm? One anchor activity per day. Something to look forward to – but not something that owns your schedule. Let the rest unfold. Leave space for slow mornings, spontaneous detours, and unplanned rest.
You’re not a tour group. You’re a person. You’re allowed to be one.
4. Overpacking “just in case”
The heavier your bag, the louder your regrets.
It’s not uncommon to see travelers hauling oversized suitcases through cobblestoned streets, dodging puddles, staircases, and confused stares. You can almost hear the internal monologue: Why did I bring a hairdryer, three jackets, and enough outfits for a month-long photo shoot?
Overpacking is rarely about logistics. It’s about fear. Fear of not having enough, not being prepared, not being able to cope. But here’s the truth: most people return home realising they wore the same few things over and over.
You won’t regret packing light. You’ll regret the awkward Tetris game of fitting a bloated suitcase into the trunk of a shared taxi. You’ll regret the stress of unpacking items you only used once.
These days, I treat packing like editing. If it doesn’t serve multiple purposes, it doesn’t come. A single black dress that works for dinner and daytime. A pair of shoes that can handle both sidewalks and spontaneity.
Most “what ifs” can be solved with a laundry sink and a bit of creativity.
5. Forgetting travel insurance
I’ve never been hospitalised overseas. I’ve never had my luggage stolen or flights cancelled by volcano ash. But I still buy travel insurance every single time.
Why? Because I want the right to panic. The permission to call someone when things go sideways. The knowledge that if I fall off a scooter in Bali or contracted a disease in India, I won’t be bankrupt on top of everything else.
It feels unnecessary – until it’s not.
If it’s a short trip, the cost might feel like a waste. But if it’s a long trip and you don’t have it, the risk multiplies. I see it as a small tax for peace of mind. A gamble where I hope to lose.
6. Losing money in exchange transactions
Once, I had already prepared some foreign currency in advance. But then – standing in the airport just before departure – I hesitated. What if it’s not enough?
So I exchanged more.
The rate wasn’t great, but I told myself peace of mind was worth it. Later, I checked and realised how much I lost in conversion and fees. It wasn’t a massive amount, but it annoyed me.
These days, I stick with what I’ve planned. I carry some cash, but mostly rely on e-wallets like BigPay or Touch n’ Go. (I’d try Wise if either one isn’t available.) Currency apps like XE show me live rates so I don’t get surprised.
Turns out, trusting yourself is also a form of travel preparation.
And just a note for cruise ship travellers – the currency booths set up right outside the terminal or near the gangway often offer poor rates too. They're convenient, yes, but you’ll likely lose more in the exchange than you think.
7. Not understanding the local culture
In India, I once ate with my left hand at a friend’s home. My Malaysia friend fiercely nudged me.
I’d forgotten: in many parts of India, the left hand is traditionally reserved for… less sanitary tasks. Eating with it, especially in public, can be deeply offensive.
The thing is, no one yelled. No one scolded. But that doesn't mean it went unnoticed.
Culture isn’t just food and festivals. It’s gestures, timing, tone. It’s the pause before you enter a temple. The way you greet an elder. The fact that you take your shoes off without being told.
Some of the deepest respect is invisible. And some of the best travellers are the quietest observers.
8. This wasn’t exactly a language barrier…
In an eatery somewhere in the southernmost city of China, I confidently ordered food for my Indonesian friend and me.
“你好，请给我一个不辣的火锅，不要鸡脚。谢谢！”
(Hello, can I have a non-spicy hot pot, without chicken feet? Thank you!)
The waiter nodded enthusiastically and came back with a steaming bowl… full of chicken feet.
The problem wasn’t pronunciation. It wasn’t about not learning local phrases. It was me – confidently pointing at 凤爪, thinking it meant some kind of chicken skin or maybe just a fancy name for a boneless part.
*Translate 凤爪 into English*
Exactly what I didn’t want.
I’d tried to use the local language and still messed up. My Indonesian friend looked horrified. So was I.
These days, I still learn a few key phrases – thank you, sorry, how much – but I also point, gesture, and smile a lot. And I never pretend I know more than I do.
You’ll make mistakes – it’s part of the journey. But if you learn from them, they become stories worth telling.
What’s your funniest travel mistake?
My other posts that can help you travel smarter:
