Introduction

We often have this somewhat perfect image of travel: incredible sunsets, magical encounters, moments of total freedom… and no one really talks about the moments when you think: “okay, that was a bad idea.”

The truth is, traveling also means making mistakes. And even after several trips, you keep making them. Small ones, big ones, funny ones, the “how did I think this was a good idea?” kind.

Over time, I realized that these mistakes are just as much a part of travel as the beautiful moments. And sometimes… they even become the best memories.

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Mistakes while traveling (and why it’s normal) ⚠️

Rushing between islands in the Philippines 🏝️

In the Philippines, I had a very ambitious mission: “see as much as possible.”

The result? I once ended up doing two islands in a single day. On paper, it looked efficient. In real life, it was mostly running with my backpack, stressing about ferries, trying not to miss the next connection, and constantly carrying that little pressure of “okay, I need to keep things moving.”

I wasn’t really taking the time to settle in, or to breathe in the place I was in. I was already mentally at the next destination before even understanding where I had arrived. And in the end… I didn’t really enjoy it. I remember the stress and exhaustion more than the landscapes or the moments.

I saw places… but I didn’t really live them.

With hindsight, I realized something simple: it’s not a race. It’s better to appreciate what you see than to try to see everything. The place will still be there tomorrow, and even years from now. You can always go back—but you can’t really relive a moment you were too rushed to feel.

When I underestimated a country’s entry rules 😅

Another mistake that taught me a valuable lesson was not taking the time to properly read the details before entering a country. Visa conditions, entry fees, small but important rules that are easy to overlook when you’re already in “travel mode”… I skimmed over them a little too quickly.

As a result, I ended up at a border with a visa fee to pay, and not enough cash on me to cover it. One of those moments where you quickly realize that “it will work out” is not always a strategy.

In the moment, it was stressful and a bit humiliating too. But what I remember most is something else: an incredible act of kindness. People on site who saw the situation, took the time to help, and even lent me the money so I could cross the border.

It reminded me of something simple but powerful: while traveling, despite the unexpected, there is often a human solidarity that shows up exactly when you least expect it. And this experience taught me just as much about preparation as it did about the kindness of people.

Traveling with a backpack that was way too heavy 🎒

Another mistake I made on one of my trips was leaving with a backpack that was far too big and way too full.

At the time, I thought I was being “well prepared,” with everything I might possibly need just in case. In reality, I mostly had a heavy, bulky bag, and a lot of things I never ended up using. Every move became harder, every set of stairs a small struggle, and I quickly realized I was carrying far more than necessary.

In the end, I ended up doing a big clean-out along the way… and I even gave away several things. Including my nice Dr. Martens sandals (snif snif 😅). Let’s just say that at that point, I missed them more emotionally than practically.

Looking back, it taught me something simple: traveling light isn’t just practical, it’s real freedom. The less you carry, the more free you feel to move, change plans, and actually enjoy the journey without being slowed down by your own bag.

My backpack cost me a fortune in flight fees 🌍

Another mistake I made was traveling with a big backpack while hopping between several countries fairly close to each other, mostly by plane.

On paper, it made sense: one bag, everything inside, and I was ready to go. But in reality, I hadn’t really considered an important detail… the flights I was booking didn’t include checked baggage. As a result, every time I flew, I had to pay extra fees to check in my backpack.

In the end, my “practical choice” ended up costing me much more than expected, and made me realize that the type of bag you travel with should always be thought through based on your travel style.

Since then, I really try to weigh the pros and cons: am I flying often? Can I travel lighter? Is it actually worth bringing a big backpack for this kind of itinerary?

Because beyond comfort, the choice of bag can also have a direct impact on your budget… and your stress level while traveling.

When my naivety got me into trouble while traveling 💡

And finally… getting scammed.

It has happened to me a few times while traveling, and honestly… even today, it can still happen. Let’s just say I tend to be a pretty trusting person in life, and sometimes a little too naive.

When I travel, that shows up in small situations where I trust too quickly, don’t ask enough questions, or assume that everyone plays by the same rules I do.

Over time, I’ve learned to recognize certain warning signs, to step back a little more, and to double-check things rather than assume. But I think it’s also part of the learning process of travel: you get caught once… and then you learn to read situations better next time.

It’s not always pleasant in the moment, but it’s part of my journey as a traveler, and it definitely made me more attentive (and a little less naive… but not completely, I have to admit 😅).

When my fear of immigration control cost me my travel freedom ✈️

Another mistake I made while traveling was booking my next flights too far in advance, especially when I was hopping between several destinations.

Honestly, it wasn’t really about organization, but more about fear: the fear of being denied entry into a country if I was asked for proof of onward travel and didn’t have one. So I preferred to buy my tickets in advance to feel “safe.”

In the moment, it reassured me. But in reality, it also took away a lot of my freedom. In some countries, I was indeed asked for an onward ticket at immigration—but only two or three times. And yet, that small potential stress ended up influencing several of my travel decisions.

The problem is that these pre-booked tickets sometimes forced me to leave places earlier than I wanted to. Even when I was happy, even when I wanted to stay longer, I found myself leaving just so I wouldn’t lose the money from the ticket.

And even today, this is a mistake I still think about often. I’m still researching better ways to handle it without locking myself into my travel choices.

I’ve realized that everything depends on the type of border. When it comes to land crossings, it’s much simpler: a cheap bus or train ticket is usually enough to prove onward travel, without too much financial risk if plans change. But with flights, it’s a different story.

I’ve also heard about certain apps or services that let you “reserve” a ticket without paying the full price, just to have temporary proof in case of a check, and then cancel it afterward. I’ve never tried them myself, but it’s something I keep in the back of my mind.

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Conclusion

Of course, these are not the only mistakes I’ve made while traveling. There have been many others—small and big, sometimes funny, sometimes less so in the moment. But these ones remain the most meaningful, the ones that truly shaped the way I travel.

Over time, I’ve come to understand that these mistakes don’t define a bad trip. On the contrary, they are part of the experience. They taught me to prepare better, to slow down, to observe more, and above all to accept that travel doesn’t need to be perfect to be memorable.

And if there’s one thing I’ve learned… it’s that I will probably keep making more of them. But at least now, I know I’ll be able to laugh about them afterward.