Travel Mistakes We'll Never Make Again
Updated:
Nov 14, 2025
5 min read
We’ve all been there. Wide-eyed, in a foreign land, full of glee. You no longer feel the sharp ache of life’s shackles, those burdens feel a million miles away. The butterflies in your stomach remind you that you’re on your path. You’re doing you. You’re alive!
And damn, is that not the most intoxicating feeling? That's what travel is about.
But then there are those moments in travel that we don't always talk about, when those butterflies suddenly turn into a giant pit.
Missed flights, forgotten passports, ten years on a secondary security screening list… Our members and the team at Jack’s recently shared those travel mishaps they hope never to repeat. And honestly, some of these are a masterclass in exactly what not to do.
Except our Editor, Katy, that is. When asked, she simply said: “I’m really a very good traveller, so not much stupidity to offer.” An admirable stance. A suspicious one, but admirable…
Here are some of our favorites (and a handful of lessons we’ve learned right alongside you).
From Bali to… Frostbite?
“When our visa for Indonesia couldn’t be extended, I booked a week in Shanghai in February. While it was 25°C in Indonesia, we arrived in Shanghai to 0°C and frost!
Also, it was Chinese New Year — everything closed, no food stalls, not even local eateries. We made the best of it and booked tourist excursions until we could go back to Indonesia.” - Elisabeth
Going from beach vibes to freezing winds wasn’t quite the mid-trip refresh Elisabeth had in mind—but hey, at least she got to experience a very different side of Asia - sans dumplings.
Our takeaway: Always check the weather and the national holidays before booking that spontaneous side trip.
Never again - Gambia.
“Never go to Gambia ever again - rubbish on beaches, sea too rough to swim in, and constant harassment by locals asking for money.” - Kaminee
Our takeaway: Sometimes a destination just doesn’t click - and that’s okay. Not every beach is a paradise, and if you’re looking for just a quick sun holiday with your creature comforts, there might be better places. But we wouldn’t write off Gambia just yet.
Where the country shines is in the interior and on its river. Take a journey upriver, either as a day trip or a multi-day excursion, and you'll have the opportunity to learn more about the true Gambian lifestyle.
Whether that’s spotting chimpanzees, cruising along the Bao Bolong Reserve, or visiting megalithic stone circles and traditional villages, can you really say you’ve seen Gambia without venturing into its interior?
Mardi... Nah
“Going to New Orleans during Mardi Gras. What a dump! It’s a dirty city, and Mardi Gras brings out the worst. Nowhere really felt safe at night, even the supposedly ‘safe’ areas. I have never seen so many drunk people and vomit as I saw in the French Quarter. Horrific”- Adrian
Adrian’s short and brutal review of one of the world’s most famous festivals says it all. Not every big event is worth the crowds - or the vomit on your shoes.
Our takeaway: If you do plan to visit New Orleans during Mardi Gras, this Reddit guide is packed with tips.
Overpackers Anonymous
“Taking too many things on our trip to North and Central America meant we had to take an extra hold bag. Costing £70–£110 each flight we took!” - Albert
That “just in case” sweater and 10 more pairs of underwear? Not worth a hundred quid per flight.
Our takeaway: Give our genius one-bag packing hacks a read - non-negotiable.
Leaving the hotel... and forgetting where it was
“This is basic, but leaving the hotel in a foreign country and not remembering its name or address so you can get back to it.” - Robin
Our takeaways: A quick photo of the entrance (or a pin on Google Maps) can save you an embarrassing game of charades with taxi drivers.
Jack's Team Confessions
Fleeing to The Jungle Peak Pandemic
“Worst travel mistake by far was trying to navigate international borders mid-pandemic to avoid lockdowns. With all my belongings and two kittens in tow, I left Slovenia, aiming for Costa Rica.
What should’ve been a simple one-stop flight turned into a four-day odyssey through Italy and Spain thanks to sudden border closures. In total: six trains, two planes, two overnight stays, and a seven-hour hitchhike into the jungle.
Just before my final flight, I realized I’d forgotten to provide proof of onward travel - so there I was, in the boarding line, frantically booking a random cheap ticket to Guatemala just to save my butt.
By the end, we’d lost €600 in flights (thanks to an OTA that refused reimbursement after Austria closed its borders), one laptop at the side of the road, one pet passport, one shoe, and, if we’re counting, a good chunk of my sanity.” - Kash, Community & Content
Our takeaway: Still processing this one.
The Long Way Round
“I once flew to Sri Lanka, doing 4 flights total because it was cheap. I got charged £50 on two flights for oversized bags, then £120 in Saudi Arabia for a visa during a 3-hour layover. Ended up costing more than flying direct and took 30 hours longer.” - Ian, Marketing
The thrill of a “bargain” flight can quickly fade somewhere around hour 4454545353 of travel and £200 in hidden fees. Yuck.
Our takeaway: Sometimes the more expensive ticket is the cheapest one in the end. Do a bit of digging before pulling the trigger on booking that dirt-cheap flight.
A Taxing Arrival
“Landing in Egypt without pre-organized transport or a working e-sim. I thought I’d just book an Uber on airport Wi-Fi - NOPE. Suddenly I was surrounded by 15 men shouting for my fare. I agreed on a price, got in, and the driver sped off while demanding more money. Somehow, I arrived alive.” - Lauren, Flights & Socials
“Outside Dar es Salaam airport, every Bolt driver kept cancelling. We ended up sharing taxis with other Jack's members heading to the Zanzibar dock. When we finally found our ‘driver’ in Zanzibar, he’d paid a six-year-old to hold our name sign while he sat in the shade up the street.”- Robyn, Marketing
Our takeaway: Pre-arranging your first ride may not be the cheapest option, but it will likely pay off in comfort and sanity.
Ten Years on a List
“I was flying from Singapore to Canada with a layover in the US. I checked something legal in both countries, forgetting it wasn’t legal in between. Got written up and put on a list for ten years.” - Kristi, Flights Lead Canada
Our takeaway: Legal in one place doesn’t mean legal mid-transit; do your research, friend.
So now you know our regrettable travel moments, it's only fair that you tell us yours! What's the number one thing you'll never do again while travelling? Let us know in the comments!
