When Travel Goes Wrong: Real Travel Fails, Hard Lessons & How to Travel Smarter

For every dreamy travel photo you see online, there’s usually a moment behind the scenes where something didn’t go to plan. A missed flight. Accommodation that looked nothing like the photos. Or that sinking feeling when you realise you’ve packed your itinerary so tightly there’s no room to actually enjoy the trip.

After more than 20 years of travelling, often squeezing bucket-list adventures into annual leave, I’ve had my fair share of travel fails. And while they were frustrating at the time, they’ve shaped the way I travel today far more than the “perfect” trips ever did.

In this episode of Tourist to Traveller, I’m getting honest about when travel goes wrong, what those moments taught me, and how you can avoid common mistakes... without overplanning, stressing yourself out, or losing the joy of travel.

What You’ll Learn in This Episode

• Why travel going wrong is more common than social media makes it look
• My most memorable travel fails (and what I learned from each one)
• How travel fails can actually make you a more confident traveller

Helpful Resources & Links

• Free Resource: Travel Planning Like A Pro In 5 Easy Steps
  A practical guide designed to help you avoid common travel mistakes before you book. Perfect for busy travellers who want better trips without overthinking every detail.

And if this episode resonated, explore more Tourist to Traveller episodes to help you travel with confidence, clarity, and intention. 

Connect & Explore

Find destination guides, travel planning resources and more at touristtotraveller.com, and follow along on Instagram @_touristtotraveller for behind-the-scenes planning and future travel inspiration. 

Transcript

Speaker 0:00

Welcome to the Tourist to Traveller Podcast, the show that helps you go beyond the guidebook and turn your bucket list dreams into real adventures. I'm Tahnee, a travel blogger, podcaster, and everyday explorer who's been ticking off epic destinations for over 20 years while balancing a 9 to 5. Each week I'll bring you inspiring stories, destination deep dives, and practical tips to help you plan smarter, travel deeper, and capture those unforgettable moments along the way. So, grab your passport, hack your curiosity, and let's get started. Alright, let's get real for a second. Because for every dreamy sunset photo and bucket list moment you see online, there's usually a travel foul lurking somewhere behind the scenes. A misconnection, a combination that looked very different online, or that sinking feeling when you realize you've planned something that just doesn't align with how you actually like to travel. After more than 20 years of traveling, often squeezing epic trips into limited annual leave and have my fair share of things go wrong. And honestly, those moments have taught me more about travel than the perfect trips ever did. So in today's episode, I'm sharing my biggest travel fails, what I've learned from them, and how you can avoid making the same mistakes without overplanning, stressing yourself out, or losing the joy of travel. Think of this as a judgment-free chat with a friend who's already learned the hard lessons, so you don't have to. This is your typical Instagram versus reality conversation. Often the pictures, the stories that people share about their travels are everything that went right. It's the juicy, brag-worthy stories that people want to share. However, in reality, things go wrong. And I think it's time we normalize travel going wrong. Because let's face it, it happens. Sometimes travel fails come from rushing, under planning, overpacking, but often it is also something that is completely unavoidable and out of your control. So I'm really excited to share with you my most memorable travel fails and what I've learned from them. Travel fail number one, and this is my most recent. I recently was traveling to the US and I had a very brief two and a half hour stopover in Dallas. I knew the weather at my destination. I knew that I wouldn't be leaving the Dallas airport, and I thought I packed accordingly. What I didn't know was there was a snowstorm. A once-in-a-century snowstorm that was happening in Dallas and across a lot of the US. So initially I was looking out at my window at the beautiful snow, and I live in Queensland, Australia, where it never snows. So I got incredibly excited. My jaw dropped, and I thought, wow, how beautiful is this? How lucky am I? Until we landed, and we realized that we might be stuck on the tarmac for hours because they had to clear the snow and there were no uh aerobridges or gates available for us to get off the flight. Now that was just the start of my travel fail. I then got a notification to let me know my connecting flight had been canceled. So eventually we get off the flight, we're on the ground, and it was minus 11 degrees, sorry, minus 12 degrees Celsius outside. It was freezing, and that short walk across the aerobridge from the plane to the terminal, I have never been so cold in my life. And I get cold on planes and I pack accordingly, but it wasn't enough. It was so cold in Dallas. Now, luckily enough, I had to grab my bag and then take it to the next terminal for my domestic flight, which I did, and I was able to grab my really thick puffer jacket out. Thank God I did. I managed to jump onto another flight, and after a couple of delays, that flight was cancelled. I got onto another flight and I stopped counting at 16 delays. After that, the flight was cancelled. Now, by this time, it is late at night, and Uber was not running because it was too dangerous outside. So we couldn't get a hotel because there was absolutely no way for us to get there. Staff couldn't get in, passengers couldn't get out. We were stuck in the terminal. They turned the heating off at some of the terminals, and inside it was freezing. Because staff couldn't get in and they were saving electricity. A lot of the cafes and restaurants and stores weren't open. We couldn't get food, we couldn't get coffee, we couldn't even get water outside of the bathrooms in our terminal. And they had a 7-Eleven there on site, and the shelves had been stripped bare. So we ended up being stuck until the next morning when we got another flight, a very restless, freezing cold night on the airport floor, and finally made it to our destination. And of course, the story doesn't end there. After staff had assured me that my bags would be with me when I landed, they were not on the flight. And at that point in time, they didn't know where they were. So I had to submit a uh a missing baggage claim. And there was a spot there for me to put my air tag details. And I thought, well, that's great. I put an air tag in my luggage because I planned accordingly. And then I went into find your into find my phone on my iPhone, and it showed me my last location for my baggage, and it was months ago in my house in Australia because the battery had gone flat and I didn't realize. So this journey was fail after fail after fail. So what did I learn from this? First of all, always pack the extra warm jacket, even if you don't think you need it. I almost didn't pack my puffer, and I'm so glad that I did. Two, always check that your AirTag battery is still working. Um, and third, natural disasters happen, and sometimes you've just got to suck it up and go with it. It was no one's fault. It was a natural disaster. I wasn't the only person stuck in this terminal. There were thousands of people who were stuck, including staff. And I was there for one night, but some people were there for two to three nights sleeping on the cold floor. So it is what it is. These things happen, and it's just part of travel. Travel fail number two. This one happened in Paris. So picture this. I'm 21 years old. My long-distance boyfriend at the time bought me a trip to Paris and the Greek Islands for my 21st birthday. I met him in Paris and we had an amazing time. We've checked out of our accommodation, and we have just a couple of hours before we head to the airport to head over to Greece. Of course, before we go to the airport, we thought we should probably top up our currency. So we go to the ATM. My partner's paying for the trip. I was a very poor 21-year-old student, and he pays for the trip. Uh, he puts his card into the ATM and it disappears. The ATM took his card. We didn't know it at the time, but he actually had not let his bank know that he was going overseas, and they thought that it was a fraudulent activity, they thought that it was fraudulent activity. Now, things get worse. I was 21. This is way before the time of having uh an international SIM that you can put into your phone or an e-sim. Um, this is back in the time where we needed to find an internet cafe or a payphone that we would put coins into. We were almost out of money, we'd already checked out of our accommodation, and to make matters worse, this was the first day of a long weekend, which means that we had to wait a couple of days until the bank opened where we could retrieve his card and continue our journey. So we were more concerned, honestly, about where we were going to stay than anything else. We ended up in an internet cafe reaching out to our families begging for some help. So I can't remember the specifics, but I think my mum had booked us accommodation somewhere that was just really cheap nearby for a couple of nights and had paid for it. So all we had to do was rock up. I honestly can't remember what we did for food over those few days, but let's say we were not splurging on anything during that time in Paris. After the long weekend, we got his card and we continued our journey. So, what did this teach me? First of all, always notify your bank before you go overseas. And secondly, sometimes things go wrong and you need to problem solve. And this includes reaching out to friends and family sometimes when you have no other options. Travel file number three. This was also in Paris, actually. Yes, it was the same trip. I got scammed for the first time. Uh, we were outside the Louvre, me and my boyfriend at the time, and some locals were showing me this friendship bracelet that they wanted me to buy. And I said, no, thank you, no thank you. They then grabbed my wrist, and one of the men tied this friendship bracelet tied this friendship bracelet around my wrist so tight and I couldn't get it off. It was tight and I could only use one hand. Then other people came to join them, and that's when we realized that this was actually a gang of guys who surrounded us. They had my partner and I separated, so he couldn't get it off my wrist either, and he demanded payment for this friendship bracelet. It was a really scary moment. I can't remember what we paid. It wasn't that much in the grand scheme of things, it was somewhere between 5 and 20 euro. Um, all we could really do was pay the money, and then they left. So I had not researched any kind of scams before I went on this trip or any trip up until this point. And that is a mistake I will never make again. Always be aware. Travel fail number four. I went to Sri Lanka, and the first part of my trip was a yoga retreat with one of my close friends, and it was incredible. And then the second part of my trip, I was solo traveling in Sri Lanka. I booked accommodation as I was getting into the car with my driver to take me from the yoga retreat to Ella in Sri Lanka. So it was very last minute, but I waited for the payment to go through and I waited till I got my confirmation before I got in the car. So we're driving to the destination, we get to Ella, we get to the hotel, the journey there is beautiful. I get out of the car, I get my suitcase out, I start to go into reception, and one of the staff stopped the driver and spoke to him. Uh, he then grabbed the bag and started taking my bag back towards the car. And I said, What's going on? This is my hotel. And he said, You can't stay here. And I said, No, this is my hotel. And I was very well aware of common scams around hotels and people not associated with the hotel standing at the front and saying that there's been a mistake and you've double booked and it's full, and then taking you to another hotel. Um, so I refused to listen. And um he told me, the driver told me that he was told uh what had happened. And now I trusted the driver. He had no reason to lie to me and had no connection to the hotel. But I said I wanted to go and speak to the staff inside to confirm. And I went inside, I went up to reception, I spoke to a staff member, and they confirmed they had double booked. They had no rooms left, but it was okay. They had booked me in at a hotel up the road. So I went to the hotel, I got out, I checked in, and everything felt fine at the beginning. They were lovely. I went up to my room, and when I got to the floor that my room was on, that was the first time I had noticed that anything was off. What I noticed was that when I exited the lift, I turned left to go to my room. That wing was lit up. To the right was not lit up, and I could see outside the glass the whole right wing of the entire hotel, all of the floors, there was not a single light on. And I thought this was very, very odd. So, anyways, I go into my room, everything's fine. Um, the standard of the hotel was fine. I went back down and I was just asking questions around the hike I wanted to do in the morning, what time was the buffet breakfast, and they kept saying, Oh, around you, we work around you. Um, I asked what I should do for dinner, and what time does reception close? And he goes, you know, we work around you, we work around you. And I didn't understand what that meant until I came back that night after grabbing dinner. It was late. It was very late. I think it was maybe somewhere between 1 and 3 a.m. And they were waiting for me with the doors open and locked it behind me. And that's when I realized they literally waited for me to get back to lock the doors. Still nothing is jumping out at me too much at the moment. Next morning I get up and I head out in the dark to do my walk, and it was incredible. I wanted to go on a couple of hikes, which I did. I came back for breakfast and they said, Would you like your breakfast now? And I said, Yeah, sure. And that's when they told me that they weren't doing the buffet breakfast, they will cook me whatever I want. And I went into the restaurant and I sat down and I was the only person there. And they cooked this whole platter of food just for me. And then I looked up and realized that every single staff member was standing around waiting for me in case I needed anything. And it was at that moment I realized I was the only guest in this entire hotel, which was first of all, really lovely that everyone was waiting on me hand and foot, but also a little creepy, if I'm being honest. Uh, and I had a great time in Ella. It was beautiful, but I was the only guest in this vacant hotel with the exception of one wing and one room and a whole heap of stuff that were waiting for me. Travel foul number five. This also happened in Sri Lanka when I left said hotel. Uh, I organized a driver through the hotel to take me to my next destination. And on the day he showed up and took me out to his car, and he then informed me that he had double booked. See, there is a theme here, and that his cousin would be driving me in a different car. And I knew that this was a scam a hundred percent, and I wanted to go back in to tell the staff, and he kind of blocked me and stopped me from doing that, and so he'd already put my bag into the other guy's car, and I was like, look, he then offered me a discount, and I said, Yeah, okay, fine, fine. So I got in the car and I drove. This cousin did not speak a word of English, so I couldn't express when I wanted food or to stop to use the bathroom or ask any questions, no English. At one point, he got out and took a break and then came back after about 45 minutes without telling me. I'm just sitting in the car waiting, thinking that he's gone to the bathroom or something. And then further down the track, he put his hand on my leg and I smacked it away and I yelled at him and he did it again. I smacked it away and I yelled at him, and then I thought, I can't get out of this car. My luggage is in the back. If I leave and he drives off, he has all of my belongings, including my passport, in the boot of this car. What am I gonna do? So eventually I found an opportunity when uh he got out of the car. I ran to the back seat and I got into the back seat, which he was not happy with, but I stayed in the back all the way to my destination and got out, yelled at him again and then left. Um, it was incredibly unsafe. And the lesson that I learned here is that I shouldn't have just accepted things. I should have put my foot down and said no, even if it meant I didn't get to my next destination on time, even if it meant I had to pay double for another driver or to find another way there, there is no way that I should have accepted that situation. And also, my passport should not have been in my suitcase. It should have been on me, on my body. So, lesson learned. Next travel foul was on my first ever group tour. I did a group tour that had some time spent in Jordan in the Middle East, and then time spent in Egypt. So it was with the same tour company, but both groups were separate, but you could buy it as a combo. I hope that makes sense. So we did the first week in Jordan. When it came time to go to the second week, I got two flight notifications to book in. When we were reading the fine print for this tour, the way that we read it was that no flights were included in the cost, only ground transportation. And I read it again and again, and that is the only way that I had ever interpreted it. So we booked the flight from Jordan to Egypt. Now, when I got two flight notifications, I went to the website, and that's when I realized that I actually had two seats booked on this flight. And my travel partner also had two seats booked on this flight because the flights were in fact included in the tour, but the wording on the website was so incredibly bad that I misinterpreted it. And I asked my travel partner how he would read it, and he interpreted it the same way as me. And I asked multiple people in our group how would you interpret that, and they all interpreted it the same way that I did, is that flights were not included. But in fact, flights were included. The tool company refused to give us any kind of refund or discount as a result. They didn't want to apologize. We couldn't cancel either of the flights because we noticed this way too late. So essentially, we'd both spent a lot of money on flights that we never had to purchase in the first place. So always read the fine print, but also, even if you think you understand it, double check with the company just to make sure. My next travel fail was also on this trip. It was also in the Jordan component of this trip. Now, with this tool company, when you when you land on the ground, you need to pay a portion of the fee in cash. We knew this in advance, we knew how much it was in advance, and we were prepared. So we met with the guide on day one. He calculated what we owed and put that into local currency. And when we did this calculation, you know, currency changes, the conversion rate changes, and he told us in local money how much we owed. And we said, Are you sure? Because we thought it was this. And he said, No, I'm definitely sure. And then he showed us the total on his phone and we said, Yep, okay. So we gave him the money and we were good to go. Also, we thought, until we get to the end of the trip on our final day. On our final day, we had a final dinner to go to. So we had money put aside for our dinner. We had a bit of spare money just in case we needed it. Uh, we already had transportation to the airport, so that was easy. So then we went and we went to a currency conversion place to get money for the Egyptian component of our trip. So anything that we had left in Jordan currency, we transferred over to Egyptian with the exception of our dinner money and the uh the extra cash that we had as a just in case. The guide then reaches out to us to let us know that he miscalculated on the first night and we owed him more money. Now, we told him what we'd done. We'd already transferred our money. Um, the currency places are now closed, but we're happy to pay it by card. And he lost it. Uh, he said we couldn't pay by card, it had to be by cash, and it had to be in local currency. And I said, Well, look, we've we've got Egyptian money, we'll give it to you in this, and then you can just change it the next day. He refused that as well. Um, the only thing he was willing to take was Jordan currency in cash direct. We said, Well, we don't have it. We actually don't know how we're meant to get it. Um, he was very, very angry with us. So we went to the to a company. We told them what happened. We went back and forth. And he was furious. And the tour company eventually said, Look, it was his fault. He's made a mistake. And he has to accept what we have on us. So we they asked, How much Jordan money do you have? And we said, Well, look, this is all we have, but also we haven't had dinner yet. And if we give him all of this, we we can't eat because we had a group tour going to a place to eat dinner where they only took cash. So we said, Well, we can't go to the final group dinner. So we'll go elsewhere where we can pay by card to give him the cash. So he was angry because he got a fraction of what he wanted. And then we had no cash left. And we told the group that, look, we're really sorry. It's been wonderful to get to know you all. Unfortunately, we can't come to the farewell dinner. We're going to go elsewhere where we can pay by card. Um, and they were so lovely that they all pitched in and bought us dinner. And they didn't have to do that, but they didn't want us to have to miss out on the final group dinner. They pitched in and bought our dinner. And we said no so many times, and they refused to take no for an answer. So uh the travel fail here was that uh once again, miscommunication, let's just say miscommunication, uh, between the tour company, uh, the guide and us. And we thought we were being really clever doing the right thing here, but in hindsight, we should have just waited to convert our currency once we got to Egypt. Now I have to say, the Egypt portion of this tour was absolutely incredible, and the guide, I could not fault him, so it wasn't all bad. Um, actually, Jordan as a destination, beautiful, highly recommend it. Right, the next travel fail was in Spain. I was traveling around the south of Spain with my sister in 2025, and that was the year that they had the worst power outage in European history. The whole of Spain and Portugal were plunged into darkness. So, where were we when this happened? Well, we were in Granada in the south of Spain. We got there early, we parked our hire car, we went into the Alumbra and we did all of our exploring. Um, and we didn't notice anything was wrong until around lunchtime where we got hungry and we tried to get food, and everywhere kept telling us that either their kitchen was closed or it was cash only or it was cold food only, and we didn't understand. Uh, but also these restaurants were packed. It was hard to get a table. We eventually found somewhere that told us cold food only and cash only, and we were desperate by this stage, so we said, yep, okay, that's fine. So we went in, we we drank, we ate. Uh, it was delicious, by the way. And then it wasn't until we went to pay that he uh he thanked us for being understanding with the with the the power. And that was the first time we'd actually noticed that, oh, no lights are on. Actually, in all of the restaurants we went to and the bars and the cafes, no lights are on. We had no idea that there was a blackout. We also uh often don't travel with a local SIM or an e-sim. So we had you know no notifications on our phone to let us know. We had no idea. So we decided that look, we'd seen everything we wanted to see, anyways. We were going to go back to our accommodation, but before we did that, our plan was to get a bottle of wine because we wanted to drink a bottle of wine on the balcony at sunset and take in the views from our Airbnb. Um, this is where we realized that every single bar, restaurant, grocery store at this point had completely closed. And we start to freak out a little bit for a couple of reasons. Number one, we want to get our wine, and number two, my sister is a type one insulin-dependent diabetic, and we we don't really have much food on us. All we have is some breakfast cereal and some oat milk. Um, by the way, she hates oat milk. The oat milk was mine. Um, we finally find this little wine and cheese boutique. Uh, we get our bottle of wine, the owner there is telling us what's going on. He's filling us in on the blackout, which we were so grateful for, and we then try and get on a bus. Uh, we had like a, I think it was like a Granada pass or something. And we were meant to use this electronic thing to get an electronic ticket to get on the bus, but there's no power. We can't do any of this. So we had to pay in cash. We didn't have small coins, so the bus drivers were angry because we didn't have small coins. They were angry because they didn't want to help us to get where we needed to go. We couldn't use any of the electronic guides because no power. Um, but we finally made our way to our accommodation. And this is where we realized that with an Airbnb, we need a code to get into the lockbox to access the key to get into our apartment. How do we get the code? Well, it gets sent to us through direct message that we can't access because there's no power, there's no phone service, there's no internet, there's no way of accessing that message if the host was even able to send it. So we saw the apartment that we thought was ours. Uh, luckily, in this building, uh, you could walk directly onto the balcony of that apartment, which is why we booked it. This huge, beautiful balcony overlooking um the historic part of Granada with rolling snow-capped hills in the background, and it was absolutely stunning and worth every penny. And we could still access the balcony. Um, there were also some shared accommodation there, so there was a shared kitchen and a shared bathroom. So we thought that's fine. Worst case scenario, we go back and sleep in the car. It's only a few hundred meters away. We have access to a toilet, we have access to a shower, and in the kitchen, we had a bottle opener and wine glasses, bowls for our cereal. We were set. We were gonna make this work. So we waited and we waited, and other people came who also couldn't get into their rooms. One guy who came spoke multiple languages, and he went up and down the street speaking Spanish to locals to find out what was going on with the blackout. Did anyone know the host? Does she live does she live locally? Um, and like none of us could get in. So we hung out together and just kind of shrugged it off. You know, it is what it is. Uh and then eventually the host, after many, many hours, came uh to let us in. She did not speak a word of English, but luckily the other guests could translate and got us into our apartment. But by this stage, it was late afternoon and we'd already been set. We were drinking our wine on the balcony looking out over Granada. And the final travel fail that I will share with you, and this one's a little embarrassing, but I'm sure some of you can relate, was a relationship breakdown that I had in the Greek Islands. I wanted to go home, but he paid for my trip, uh, flights, accommodation, um, our spending money on the ground was his. I had no way of contacting friends or family, and I was essentially stuck there with him. So the moral of the story there is that I always recommend being always have a backup plan. And this isn't just when you're traveling with a partner, it could be friends, family, anyone. If there is a relationship breakdown while you are traveling, what is your plan B? How are you getting out or getting home? What does that look like? Always have a plan B in place. So, what have travel fails really taught me from all of these experiences? Well, firstly, sometimes the story, the experience, and the memory of a trip is actually improved by things going wrong. Some of these things are way more memorable than the destinations were themselves. Secondly, travel is all about getting out of your comfort zone and problem solving. And it's not until you're in some of these situations where you really understand how capable you are. Number three, always pack that extra jacket, even if you don't think you're going to need it. Four, always have a backup plan. Number five, and I'll be really honest, I haven't quite learned this one myself, but stay connected. Whether that is with a local SIM or an e-sim, find ways to stay connected so that when things go wrong, you can reach out to people who can help you, or simply get online to bought yourself a new flight. Yeah, I'm still notoriously bad at this because I secretly love traveling while being disconnected, but I'm sure I will get there one day. I've learned that travel really is about mindset, and travel fails are about mindset shifts. It's important to know when to pivot versus when to push through. And sometimes things just happen that are completely out of your control. Natural disasters, cancelled flights, and even nationwide blackouts. Sometimes it is what it is, but you've just got to see the silver lining. And let's face it, it makes our journey so much more memorable. So if there's one thing I hope you take away from this episode, it's that travel going wrong doesn't mean you failed as a traveler. It usually means you're learning, adjusting, and getting better with every trip. Those messy moments, they're often the ones that build confidence, resilience, and a much deeper connection to how you actually want to travel, not just how you think you should travel. If you want a practical way to avoid the most common planning mistakes I talked about today, grab my guide, Travel Planning Like a Pro in Five Easy Steps. It's linked in the show notes and designed for people who want incredible trips without overthinking everything. Thanks for being here, and remember you don't need perfect plans to have an unforgettable trip. Thanks for tuning in to the Tourist to Traveller Podcast. I hope today's episode has inspired you to travel more authentically and plan your next adventure with confidence. Don't forget to head to touristtotraveller.com for today's show notes, resources, and free guides to help you plan like a pro. And if you love this episode, please hit subscribe and leave a review. It helps more travelers like you discover the show. Until our next adventure. Go beyond the tourist track and level up your travel experiences.