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It’s hard to believe that I’ve been traveling the world for the last ten years – and while I wouldn’t change a thing, it hasn’t all been rainbows and perfectly executed adventures. Along the way, there have been plenty of travel mishaps, and if anything, the mishaps have made the experiences even more memorable. 

So to celebrate 10 years of travel and over 50 countries visited, I am going to share some of the stories I’ve never told before! From hitchhiking across borders in Europe to flipping over the handlebars of my bike in Japan, these are the less glamorous adventures that don’t make the family group chat (#sorrymom). 

I want to preface this by saying that there are lots of ways I stay safe on the road! Especially when traveling solo.

I’m always on my guard, I’m usually surrounded by other solo travelers, and I never travel without travel insurance. Having travel insurance is one of the best ways to ensure that no matter what happens on the road, someone has your back. 

If you’re looking for travel medical insurance, my go-to is SafetyWing. I’ve talked about them before but they really are travel insurance for digital nomads, by digital nomads. They’ve just launched Nomad 2.0 with a better claims experience and adventure sports add-ons. You can learn more about SafetyWing here. (And if you want to learn more about Nomad Insurance 2.0 – read a post I wrote here!)

In 10 years, there’s always going to be a few mishaps. But that doesn’t mean you shouldn’t explore the world. This post is purely meant to entertain and help you stay safe! 

Travel Mishaps from 10 Years of Traveling

To kick things off… I am going to share some stories that I have never shared before. 

Hitchhiking across the Montenegro/Croatia border

Hitchhiking wasn’t the original plan but when we got to the border of Croatia, a girl I was traveling with didn’t have her passport. As the border officials started to escort her off the bus, I realized she was going to be alone and jumped off with her.

She knew exactly where her passport was – back at the hostel in Montenegro. A woman at the border checkpoint called the hostel for her and they arranged for another traveler leaving the hostel that day to bring her passport to the border. 

It seemed like it was going to be a seamless handoff. All we had to do was wait.

Hours passed but there was no kind stranger with her passport in hand. 

She started to panic and we knew we needed wifi so we walked to the nearest cafe/gas station. She had a Facebook message from the guy with her passport saying he’d left it at the border for her.

However, the passport wasn’t there. 

Turns out – it’d been taken to another border. 

The border guards loaded us in the back of their truck and drove us to the other border. When we arrived we learned that they had stamped her out of Montenegro and left her passport on the Croatian side – 3km away. No one would drive us without her passport – so our only option was to walk. 

When we got to Croatia there was no public transportation and the border officials told us there was no way a taxi would come out to pick us up. Their advice: keep walking. At that point we were exhausted, starving, and sweaty. I’m not kidding when I say an old man in a white van drove by – I stuck out my thumb and off we went. 

And that’s how we hitchhiked our way to Dubrovnik. 

Crashing my bike in Japan

Years later my clumsiness caught up with me in Japan. I was in a small, quiet village Couchsurfing. My host told me about a teddy bear museum outside of town and offered me her bike to go explore. 

I’ve never been great on a bicycle… But I also wasn’t about to pass up the opportunity to visit an entire museum dedicated to the history of teddy bears (Japan is amazing btw). So, I headed off to explore and all went smoothly until I was headed back into town. 

In Japan, they drive on the opposite side of the road to America, and this confused me on the bike. At one point, I realized I needed to be cycling on the other side of the road, and in my efforts to get turned around, the handlebars hit a pole – sending me flying right over the top of them

It was probably one of the funniest things that had ever happened in this little village. Within seconds I had every shop owner and stranger on the street around me. People were so kind, even though we couldn’t speak the same language I had several people walk me home.

Luckily, other than a very bruised tailbone, a lot of embarrassment, and slightly dented handlebars, I was fine. 

Even though in this instance I didn’t need to go to the hospital, it was important to know that I could, thanks to my travel medical insurance. Like I said before, if you get the right travel medical insurance, it will always have your back. 

Getting hit by a car in Bali

While I didn’t have to go to the hospital that time, I did find myself at a hospital in Asia later that year, after being hit by a car. 

Motorbike accidents are very common in Bali. And it’s unfortunate to have been a part of that statistic. But I can say I wasn’t driving – and the accident was in no way, my fault. Nonetheless, I found myself in shock, lying on the road and completely covered in road rash.

This story is a lot more serious – and a lot less fun. It’s a warning of safety and a reminder of the importance of travel medical insurance.  

I was getting a ride home one evening in Bali, around 10:00 at night, when the scooter I was on got t-boned. We were crossing a junction and neither driver was paying enough attention. Being on the back of the scooter, my legs were exposed meaning one leg got hit by a car and the other got torn up by the road. 

Once again, I’m incredibly lucky that nothing worse happened. I had to have my wounds cleaned and dressed and I still have nerve damage in the leg that got hit by the car. The driver of the scooter walked away without a scratch. But it could have been so much worse. 

I see people with motorbike accidents all around Southeast Asia. It is one of the most common accidents, to the point where people call it the ‘Thailand Tattoo’. My biggest piece of advice is to be careful, never drive impaired, and don’t drive if you’re not comfortable. Oh, and please wear a helmet! 

Staying prepared on the road

The best way to stay prepared and navigate mishaps on the road is by having the proper insurance. As a digital nomad, it can be really hard to find insurance that works for my lifestyle. 

That’s where SafetyWing comes in. 

Insurance doesn’t have to be boring and tedious. SafetyWing is on your side! And they’re on a mission to help you reclaim your time so you can spend it having once-in-a-lifetime adventures. Try out their new Nomad Insurance claims process to see how easy, fast, and painless filing a claim can be. 

Get insured with SafetyWing’s new Digital Nomad 2.0 Insurance today

Do you want to become a digital nomad in 2024? Here are my recommended next reads:

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Justyn Jen

Justyn Jen is a digital nomad, bookworm and Pinterest marketing expert.