When Travel Goes Wrong: My Biggest Travel Fails (And What They Taught Me)
Hours before becoming violently ill in Milos, in the Greek Islands.
Sometimes the Best Travel Lessons Come From Everything Going Wrong
You can have the best itinerary in the world. Colour-coded. Bookmarked. Saved offline. Triple-checked.
And still… travel will throw you a curveball.
Flights get cancelled. Bags go missing. Scams happen. Power goes out across entire countries. You get sick. Or you find yourself stranded in a freezing airport, questioning every life choice you’ve ever made.
After more than 20 years of travel, squeezing bucket-list adventures into annual leave, travelling solo, with family, with partners, and on group tours… I’ve learned one thing: Things will go wrong.
These are my biggest travel fails. Not to scare you. Not to shame anyone. But so you can learn from my mistakes, travel smarter, and be better prepared when things don’t go to plan.
Because they will.
Travel Fail #1: The Snowstorm I Didn’t Pack For (Dallas, USA)
I was flying long-haul to the US with a short two-hour stopover in Dallas, Texas. I checked the weather at my destination. Planned accordingly. Thought I was prepared.
What I didn’t account for? A once-in-a-century snowstorm.
Dallas was in chaos. Hundreds of flights cancelled. Runways iced over. Staff unable to get to work. Ubers not operating. Roads unsafe. A full-blown natural disaster.
Flying in, I pressed my face to the window in awe… everything was white. I’d never flown over proper snow before. I live in Queensland, Australia. Snow is not part of my normal reality.
That awe lasted until we landed… and were told we could be stuck on the tarmac for up to three hours.
Oh, and it was -12°C outside.
The airbridge was the coldest place I’ve ever experienced. The terminal heating wasn’t working. My connecting flight was cancelled. Then rebooked. Then delayed. Then cancelled again (and again and again).
Thousands of people slept on airport floors. I didn’t sleep at all… I was freezing. Restaurants were closed. The only food option was a stripped-bare 7-Eleven.
We were trapped in the airport for over 24 hours, and by the end, I had stayed awake for almost 48 hours straight.
What This Taught Me
Don’t just pack for your destination - always pack for your stopover
Carry layers, even if you “won’t need them” (my “just in case” puffer jacket wasn’t enough)
Assume you might get stuck
Travel Tip: Always keep a warm layer, socks, and a scarf in your carry-on… even when travelling to warm destinations.
Stranded in Dallas, Texas, due to a snow storm.
Travel Fail #2: Lost Luggage… and a Flat AirTag Battery
After finally reaching my destination (yes, on the same trip), my bags didn’t arrive.
Customer service couldn’t track them. All they knew was my luggage never left Dallas. I proudly mentioned my AirTag… opened Find My… and realised the last known location was my house… a month earlier.
The battery was flat.
I had done everything right… except the final, obvious check… the battery. After two days without sleep, all I wanted was a shower and clean clothes.
Thankfully, my bags arrived later that night. But the lesson stuck.
What This Taught Me
AirTags are useless if the battery is flat
Check them before every trip
Always pack essentials in your carry-on
Travel Tip: Your carry-on should get you through 48 hours without your luggage.
Attempting to sleep on the cold airport floor in Dallas during the snowstorm.
Travel Fail #3: The ATM That Ate Our Only Bank Card (Paris)
I was 21. Studying full-time. On my second international trip ever.
Paris > Athens > Greek Islands.
We’d checked out of our Paris accommodation. Had a few hours before heading to the airport. My partner went to withdraw cash. And… The ATM kept his card. It was a bank holiday weekend.
No spare cards. No digital wallets. No easy transfers. This was pre-eSIM, pre-smart everything. International calls meant coin operated pay-phones and internet cafés.
We had to miss our flight. We had no accommodation, and very little cash left.
Somehow (thanks to my mum), we survived the weekend, found cheap accommodation, and continued our trip days later.
What This Taught Me
Always notify your bank of international travel
Never rely on a single bank card
Always have backup access to money
Travel Tip: Travel with at least two cards, stored separately, plus a small cash buffer.
Travel Fail #4: Being Scammed in Paris (The Friendship Bracelet Scam)
Outside the Louvre, two men approached us with handmade friendship bracelets for sale. I politely declined.
He grabbed my wrist. Tied it on tightly, and refused to remove it. Other men surrounded us. Intimidation escalated.
The only way out was to pay.
It wasn’t a lot of money, but it was terrifying.
What This Taught Me
Research common scams before you go
Never let strangers touch you
Walk away fast and confidently (if it’s safe to do so)
Travel Fail #5: Solo Travel Gone Wrong in Sri Lanka
Sri Lanka was incredible… and also where things unravelled quickly.
I booked accommodation last-minute in Ella… Screenshotted the confirmation, and got in the car with my hired driver.
The car pulled up to the hotel and I was told there was a mistake, and they were over-booked. Initially I feared this was a scam, but I confirmed the issue with reception and they offered alternative accommodation at no extra cost at another hotel. I had no local SIM. No way to call anyone. No real choice.
The new hotel was… empty. Lights off everywhere. I was the only guest!
Staff waited on me constantly. Cooked meals only for me. Stayed awake until 3am to let me back inside. They did everything to make my stay memorable.
Lovely people. But an eerie experience.
What This Taught Me
When travelling solo, get a local SIM immediately
Avoid last-minute bookings without backup
Trust your gut, even when you’re tired
👉 Explore my Guide to Taking Your First Solo Trip.
Solo travel in Ella, Sri Lanka.
Travel Fail #6: The Driver Switch That Turned Dangerous
Later in Sri Lanka, a recommended driver arrived… then told me his cousin would take me instead.
Red flags everywhere. This was a scam, yet I felt I had no choice.
The cousin didn’t speak English. Drove dangerously. Took long breaks without explanation.
Then… he touched my leg.
I yelled. Hit his hand away. It happened again. My bags were in the boot of the car, so I couldn’t just get out and leave. Once I had the chance, I moved to the back seat.
When we arrived at my destination, I grabbed my bags and walked away without looking back.
What This Taught Me
Never accept driver swaps
Use reputable drivers only
Always have mobile data and Google Translate when travelling solo
Travel Fail #7: Missing a Dream Cruise Stop (Vanuatu)
We booked a cruise for my dad’s 70th birthday. The highlight he was most excited about? Vanuatu.
As we departed, we were informed there was a cyclone near Vanuatu and we could no longer stop there. We were so disappointed, especially dad (he still talks about it ‘till this day).
It’s no one’s fault. Unfortunately these things can happen.
What This Taught Me
Cruises change itineraries
Travel insurance matters (read the T&C’s clearly)
Sometimes, you just have to let go
Travel Fail #8: Paying for a Flight Twice on a Group Tour
In Jordan (Middle East), I realised I’d paid for the same flight twice due to unclear wording in the tour inclusions. They stated flights were not included, when in fact, only flights before and after the tour weren’t included. The result? I had 2 seats booked on the same flight…. One booked by me, and one by the tour provider.
I questioned it. They blamed me for my interpretation of the T&C’s. No apology. No refund.
What This Taught Me
Always clarify inclusions in writing (even when you think you understand them)
Don’t assume
Read the fine print… then read it again
👉 Learn more about How to Choose the Right Group Tour.
Bucket list moments in Petra, Jordan.
Travel Fail #9: Getting Seriously Sick in the Greek Islands
Fever. Vomiting. Diarrhoea (too much information, I know!). I got really sick in the Greek Islands.
I still forced myself onto a boat tour I booked in Milos… the one everyone raves about. And I spent the day curled up inside, on a bench under towels, shivering, and sleeping it off.
My family still calls it the best day of the entire trip. I missed out on the whole thing.
Shortly afterwards, I needed to find a local doctor as I was not improving… and my mum had fallen in Meteora days prior and injured her knee. We had two patients to deal with.
What This Taught Me
Rest when your body says rest
See a doctor sooner, not later
Missing out is sometimes unavoidable, and okay
Enjoying Milos in the Greek Islands, blissfully unaware I was about to become violently ill.
Travel Fail #10: A Country-Wide Blackout in Spain
I was in Granada with my sister, when the whole of Spain and Portugal plunged into darkness. It was a total blackout.
No power. No internet. No mobile service… Which meant no access to our Airbnb we were due to check into that day.
We booked this Airbnb for one reason… the views from the balcony. We planned on sipping wine on the balcony at sunset, looking over Granada, with snow capped mountains in the background.
We had:
One bottle of wine
A little cereal and oat milk
Access to the balcony
A plan B to sleep in the car
We banded together with fellow travellers who were also stuck outside, unable to check-in. Luckily there was a communal kitchen that was open, with access to wine glasses, and a bottle opener.
We shrugged it off and stuck to our plan… we drank our bottle of wine as we watched sunset from our balcony… and ate cereal for dinner. Eventually the host arrived to let everyone into their rooms.
It became one of my favourite travel memories of the trip.
What This Taught Me
Stay calm
Make a plan
Locals and fellow travellers are often willing to help
Travel builds problem-solving skills like nothing else
Locked out of our Airbnb in Granada during the 2025 blackout, and making the most of it.
Travel Fails Make Better Travellers
Every travel fail taught me something… How to adapt. How to advocate for myself. How to stay calm. How to problem-solve. How to trust my instincts.
Travel fails make your trip all the more memorable. Travel doesn’t make you fearless. It makes you capable.
And that’s the shift from tourist to traveller.