A Chronicle of My Travel Fails

The early days of my first European backpacking trip, I was in Naples, Italy, and thought hey, it wouldn’t be too hard to train all the way to Valencia, Spain.

I told the teller at the train station, who nodded and printed out my ticket. Thinking I had suavely coordinated my travel for the day, I boarded at the indicated platform and popped in my headphones. With no phone (it was 2008 and I rejected the notion of traveling with a mobile) I had no clue if I was headed in the right direction. After some extensive napping I awoke to find that our train had ...driven onto a ferry? I didn’t have a map, but I had the intuition to know that if we were traveling over water I was probably on the wrong train. Sure enough, I ended up in Sicily, Italy’s southernmost point, where I was forced to sleep the night in a train station in Palermo. I never made it to Valencia.

Lesson learned!?

Study your maps! With mobile phones and great offline map apps like maps.me, it is much easier now to know exactly where in the world you are. I’ve now made it my practise to look at the route that my train, bus, ferry or rickshaw is meant to take, so that if I am on the wrong vehicle, I can sense it sooner. It’s great that we now carry GPS technology, but technology sometimes fails - and its impossible to predict when it will.


One morning I peacefully  awoke in Trinidad, Cuba, ready to be picked up by a driver who would take me to my next destination. I confidently hopped into the car with my minimal luggage; one daypack. About an hour into the drive, a thought popped into my head. Where was my passport? I searched the usual spot in my pack, and it wasn’t there. I instantly knew: it was hidden in the room where I’d stayed the night before. To the disappointment of those sharing my ride, we were forced to drive an hour back to Trinidad, where my Cuban homestay host was waiting, laughing, with my passport in hand. And now I reveal an amateur secret of mine: when I have no locker access, I like to hide my passport in my pillowcase…

Lesson learned!?

Perhaps the passport in the pillowcase is a bad idea, but in the context of this particular trip, I felt more secure leaving it hidden in the room than carrying it on me. The real lesson here is to always do your checks: phone, passport, wallet, camera. This seems like common sense, but it is so important to religiously integrate this check into your routine, especially before any transit.


My partner and I had just landed in Nicaragua, and after a long trip from Managua airport to Granada, we craved beer. We made our way to the closest corner store with some local currency in our pockets. Figuring all beer would be reasonably priced, we grabbed some cold ones from the fridge and paid up. Upon return to the hostel, ie a wifi zone, we did the conversion only to realize we had just paid 18 USD for 2 beers. Moving forwards we were WELL aware of how many cordobas equalled a dollar, and how much a Nicaraguan beer should cost… 50 cents.

Lesson learned!?

Always check the conversion rate before making purchases. In our case, this was not a huge loss, but others have no been so lucky. I typically figure out the equation to calculate conversions on my phone, and before buying anything I verify what the price works out to in Canadian dollars. You can also download various offline maps which will perform these conversions for you!  Another trick is to ask other backpackers when you first enter a country about prices: standard price for water, beer, street food, and transport.