Our Worst Travel Experiences & How You Can Avoid Them

Traveling is just like any other part of life – it doesn’t always go our way. We’ve had our fair share of unfortunate events while out in the world, some caused by our own fault and some not.

From each of our worst travel experiences, we’ve learned something from every incident which taught us how to better prepare for next time. The most important lesson we’ve learned from all of the dilemmas we’ve endured while travelling is to take it for what it is and not let it ruin your entire trip.

A misadventure is still an adventure nonetheless.

In this post, we want to share a few memorable bad travel experiences which made us learn our lessons the hard way.

Our worst travel experiences have essentially evolved into our best travel tips. Keep on reading so you don’t have to follow in our footsteps!

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Is It Easy to Travel a Lot?

Whether some avid travellers may never admit it, travelling sometimes sucks. Yeah, I said it! There are times where we cannot wait to finish driving a 7-hour journey and just get into bed after a long day.

Rushing through airports to make a connection in time while dripping in sweat? Forget it. Now, multiply these feelings by ten if you’re travelling with kids (let along young kids) and it’s truly a wonder why we choose to do it all over again and again.

As with anything that’s worth doing, it can be challenging but you have to really love it. So it’s a good thing we are in love with travelling because in the end, this is what fuels us to get through the rough times.

There’s no use in pretending that every trip will be perfect or that something won’t go according to plan because frankly, life just doesn’t work that way.

What you can do is learn from past mistakes and become better at travelling with practice. Or, at least learn from our stories and save yourself the hassle.

Our Worst Travel Experiences

1. Putting the Wrong Type of Fuel in a Rental Car

Not only is this one of our worst travel experiences, it’s one of our firsts. Many years ago, we rented a car in Europe for the very first time with plans to road trip through France.

As one can imagine, many things were racing through our minds to make sure we 1. had a wonderful trip and 2. made it back in one piece.

Overwhelmed by excitement, it didn’t dawn on us to think about fundamentals like refuelling. After picking up our rental car in Paris, we headed south.

By the time we reached Bordeaux, we needed to gas up the car. After pulling into the gas station, we reached for the diesel pump and starting filling up our Fiat. 

We never made it out of the gas station parking lot after the car sputtered and died just moments after we started it. The Fiat was gas powered and absolutely did not like that we filled it up with diesel.

We had to call the rental car company in order for them to come tow the Fiat away and drop off a replacement for us. This delayed our road trip by only a few hours since the rental company was prompt, but we imagine it could have been a worse situation with a less reputable rental agency. 

How to Avoid This Travel Mistake:

Ask essential questions about your rental car before leaving the car rental lot. If you’re not sure or only semi confident, ASK!

Clearly, knowing what type of fuel your rental car takes is crucial. After this, you’ll want to be completely certain on how to open up the gas cap and so on.

To our defence, France is one of the most confusing places for refueling in Europe. In France, “gazole” is actually diesel, despite it looking like the word “gas” which ultimately led us to our wrong decision.

On the other hand, gasoline can go by the names of benzin/benzina or sans plomb. You can’t blame us entirely for making this mistake, right?!

2. Visiting a Popular Destination in July

From time to time, a proper summer holiday is planned with one priority… it needs to be scheduled for the summer. Naturally, the weather is nice and people have the best chance of taking time off from work or during summer break when travelling with kids.

Although it sounds like the perfect idea, it can also significantly turn into a bad travel experience if you visit the wrong destination. Taking a vacation in June – August to a widely popular destination almost makes the entire trip not worth it.

Summer holidays means crowds and lots of them. 

For us, Mallorca specifically comes to mind and should be avoided at all costs during peak months. There are just too many people and over tourism has unfortunately ruined such a beautiful island.

The famous sites and renowned Mallorca beaches you see on your feed, are unbearable during the months of July and August. Naturally, us being us, we still found secluded places to visit on Mallorca.

Enjoying hidden gems on the island instead turned one of our worst travel experiences into a memorable one.

How to Avoid This Travel Mistake:

Visiting a place with a lot of tourists versus none can make or break a trip. How do you avoid other travellers? Well, sometimes you can’t entirely but there are still ways to at least minimise the amount of people you’ll run into.

For example, travel during shoulder season. This is one of the most common travel tips and for good reason. There are so many benefits to planning a trip for off months including lower accommodation costs and open availability for tours and activities. 

If summer is the only time you can make a trip happen, there is still one sure way to steer clear of mass tourism. Do not travel to incredibly popular places.

The world is large and filled with ideal summer destinations that are off the radar. You just have to search a bit outside the box. Thinking of visiting Mykonos? Choose an underdog Greek island like Kythira instead. 

3. Not Finding Dog Friendly Accommodation

We booked an apartment on Booking.com for a short stay in Ulcinj, Montenegro. Upon arrival, the owner saw our larger than life dog and decided that she did not want to host us.

She spoke English well enough where I was able to ask “then why does your listing say you allow dogs?” As we stood there confused and equally as frustrated, we had to face the fact that we were simply being refused our reservation due to our dog.

From the car, I hopped back online to find an alternative. Given the fact that Ulcinj isn’t exactly Barcelona, the number of places you’re able to find online are slim as it is.

Montenegro also isn’t the most dog friendly country which means, our chances of finding a place to stay in the next couple of hours that will allow our dog were diminishing.

I booked another apartment nearby and on our way there, messaged the owner to give them a heads up about the dog in an effort to not repeat the same mistake. With our luck, this apartment also didn’t want to accept a big dog so we were denied before even arriving.

This process repeated itself one or two more additional times before we gave up on the internet. We then relied on the old fashioned strategy of walking into any establishment that had “hotel” written on it just to ask if they had an available room for us and our dog.

We were basically turned away by the entire city of Ulcinj. My final attempt was successful after 4 hours of driving around the crazed streets and in 100°F degree weather. We were so exhausted from this experience that we didn’t leave the air conditioned apartment for the next 24 hours. 

How to Avoid This Travel Mistake:

Although we had zero problems finding dog friendly hotels and Airbnbs in neighbouring countries, we should not have assumed that all Balkan states will be the same.

From our time in Montenegro, we learned that big dogs (no matter how well mannered or trained) are simply not conventional when it comes to domesticated pets in Montenegro. Therefore, most people are cautious and do not want them in their homes or buildings.

To avoid this being one of your worst travel experiences, do some research on how pet friendly a country is so you know what to expect. Furthermore, always make it a habit to let the hotel or apartment know you’re explicitly travelling with a dog, even if their listing already says “pets allowed.”

4. Missed Connecting Flights

Comparatively, this isn’t at the top of the list of our worst travel experiences but it’s still a setback nonetheless. If you’re like us, you may always be attracted to the shortest flight paths with the least amount of layover times when searching for flights.

So, when booking a flight from NYC to Bangkok, I wanted to minimise the long journey as much as possible. Our flight path included a one hour stop in Beijing before our arrival in Thailand. On paper, this looked like a fantastic and efficient idea.

In reality, we were very wrong to choose this route.

As soon as our departure time in NYC was delayed, I could tell the rest of the journey was doomed. During the flight, attendants were already distributing the plans for everyone who was affected by the delay.

Upon arrival, we were herded to customer service where they handed us vouchers for an overnight stay at a nearby (questionable) hotel with transportation included.

That evening, we were fed a bowl of instant noodles with a hot dog in a squeezable tube.

How to Avoid This Travel Mistake:

First, the airline we booked wasn’t necessarily an award winning company. It even had an online reputation for not flying on time. If you do decide to risk it with a short layover, look up some reviews or data on past flights to see if you’ll actually make it. 

Secondly, keep in mind the size of the airport where you are transferring. For example, Beijing’s airport is a major transportation hub in Asia. This typically means physically getting from one gate to another takes time. 

Lastly, absolutely do not book a flight with a layover less than one hour if you are checking bags. When a connecting flight is delayed, luggage is deprioritized. This means it may not make it on the flight with you. At that point, your bags could meet you at some point down the road or, never.

5. Leaving Behind Passports on an Island

During our first international trip together, Alex and I visited Greece with our friends. We started our Greece trip in Mykonos and later took a ferry ride to the island of Santorini.

Once we arrived in Santorini and began unpacking, our passports were nowhere to be found. As my gut sank to its lowest point, I realised I had left them in our Airbnb in Mykonos.

The irony was, I was trying to keep them safe by not carrying them around with us and therefore tucked them away in a drawer. When we were packing up our things to leave Mykonos, it escaped my mind to check that drawer.

We were amateur travellers during this time! So this incident was quickly engraved into our minds as one of our worst travel experiences.

The first thing I did was contact our Airbnb host in Mykonos to let them know that the passports were left behind so they would know to hold onto them for me. The next step we had to figure out was a ferry ride back to Mykonos to retrieve the passports.

There were no available ferries until the next morning so we couldn’t do much besides wait. The travel time between the two islands is around 2.5 hours. After traveling to and from the ferry ports, onboarding the boat and collecting the passports, we spent the entire following day in transit.

This whole ordeal caused us to unfortunately lose an entire beautiful day in Santorini.

How to Avoid This Travel Mistake:

Aside from the obvious recommendation of simply remembering your things, make it a habit to open all the drawers, dressers or cabinets of your hotel before you leave.

To this day, it’s a ritual we perform whenever we’re packing up to leave our stay. Another helpful tip is to ensure you have good communication with your hotel or host. This can get tricky with Airbnb stays since you don’t always meet the host or a person during check-in.

Ensure you have a contact for a real human being who could possibly help you in case you do forget anything.

6. A Luggage’s Case of Mistaken Identity

While boarding a completely full flight, I was one of the last passengers to get on the plane. Of course, there was no room for my carry-on bag near my actual seat so I had to shove it wherever there was availability.

After rearranging some items, I forced my North Face backpack in an overhead compartment about 15 rows in front my assigned seat.

Upon landing, I went to pull my bag down from the bin and it was no longer there.

Instead, I saw another grey North Face backpack about two bins down. I immediately knew what happened – someone had mistaken my backpack for theirs. I snagged the imposter of my backpack that was left behind since it had a badge on it with some contact information.

Unfortunately, it wasn’t very helpful. I had no idea if this person had already left the airport or worst, was getting onto a connecting flight with all of my things.

I rushed to the airline’s counter to explain my situation in hopes to track the person down. After providing the name of the person written on the backpack, I was denied help.

Apparently, this was a policy violation of sharing customer information. The fact that someone accidentally stole my belongings, was not a violation. As I continued to beg, one merciful employee agreed to help me and told me which gate I could find this person before they boarded their next flight.

This person seemed completely unaffected by the fact that they almost left all of their things with me. We nonchalantly exchanged our backpacks before departing on our separate ways.

How to Avoid This Travel Mistake:

It turns out, those fabric ribbons or kitschy bag tags in the shape of a pineapple aren’t silly after all. It’s actually an extremely helpful trick if you have a common looking piece of luggage.

Whether it’s a checked luggage or carry-on bag, make your item stand out. There should be no possibility that someone would mistake it for their own. 

7. Ups and Downs of Road Tripping

We’re devoted road trippers which means we’re constantly exploring by car. Needless to say, this adds an entirely new level of things that could potentially go wrong. And guess what? They have!

From trivial fender benders, mechanical breakdowns to a full blown accident, we’ve experienced our fair share of troubles on the road. Some of the more serious occurrences weren’t just bad travel experiences, they were just unpleasant times in general.

Our most notable incident was a car accident in Sicily which actually launched us to purchasing an entirely new car. In addition to this, we’ve made a handful of impromptu stops at mechanic shops.

Sadly, some of these visits ended up being much more expensive than others. Unquestionably, this is the worst part about road trips but for us, the benefits continue to substantially outweigh the downsides.

What we learned from each of these instances is that things will continue to happen. Aside from putting our best foot forward, there’s no sense in stressing about everything we cannot control. 

How to Avoid This Travel Mistake:

This last experience is not a travel mistake, but a tip on how to be proactive when travelling. The easiest thing you can do to protect yourself and your trip when travelling is to be insured.

It’s unfortunate but we know that some of our worst travel experiences could have panned out much better if we were properly insured. The type of insurance that travellers can benefit from is overall travel insurance, rental car insurance and even flight insurance.

Travel Resources for the Best Travel Experiences

☔️ TRAVEL INSURANCE: EKTA or VisitorsCoverage

✈️ FLIGHTS: Skyscanner, CheapOair or Kiwi.com

🚙 CAR RENTALS: Discover Cars or Rentalcars.com

🚊 TRAINS & BUSES: Busbud, Trainline or Omio

🛳 FERRIES: Direct Ferries

🛌 ACCOMMODATION: Booking.com, Agoda or Trivago

☎️ ESIM / CELL PHONE DATA: Airalo

📸 TOURS & ACTIVITIES: GetYourGuide or Viator