7 of our Worst Travel Failures Yet (and 7 Lessons Learned)

From trekking through the humid Peruvian Andes and riding Vespas through the sun-drenched hills of Tuscany, to watching sea turtles hatch on a pristine beach in Costa Rica and rafting over river rapids in Bali, we’ve embarked on some pretty unforgettable adventures.

All of those experiences, though, haven’t been without the inevitable mistakes, flaws, frustrations, and downright failures.

Sometimes, we look back at those oversights and laugh at ourselves. But other times, we cringe at how much money we wasted unnecessarily or at how oblivious we were.

Traveling is never as picture perfect as it looks online, and it almost never works out the way you planned it to. But that’s why traveling is so beautiful, and so essential to learn and grow as a human being.

You make mistakes, and you learn from them. You end up in the wrong place, but you come away with a hilarious story. You try a dish you can’t even pronounce, and discover your new favorite meal. You leave your comfort zone behind, and life abroad unfolds unexpectedly before you.

From getting hopelessly lost, to missing the last flight home, things happen. That’s why it’s vital to do your research, think on your feet, ask questions, and practice (by traveling more!). And when all else fails, sometimes, there’s travel insurance for that.

Today, we’re teaming up with Generali Global Assistance to share some of the biggest travel failures we’ve experienced over the years, and what we learned from them!

7 of our Worst Travel Failures Yet

(and 7 Lessons Learned)

1. Overpacking

One of the worst ways to start any trip is with a bulky, overweight suitcase. And even worse, is bringing more than one suitcase.

In addition to the crazy overweight fees airlines charge (sometimes over $50 per bag, one way), carrying those bags around is a struggle.

On our first two-month trip to Europe in 2014, we each packed one large suitcase and one small carry-on suitcase. Plus Mauricio had a small daypack and I had a tote bag. What on earth did we need all of that stuff for?!

That summer, we spent the majority of our time at our apartment in Madrid; however, each time we moved from place to place, it was painful.

Here’s just one of the many examples. When we arrived in Barcelona on a sweltering July day (I’m talking nearly 100°F/28°C), and discovered that all of the city’s taxis were on strike due to an uproar about Uber, we had to drag all of our luggage around town, over cobblestone streets, searching for our apartment. Seemingly hours later, we finally arrived at our place, drenched in sweat and in the worst of moods. And of course, our apartment just so happened to be on the fifth floor, with no elevator, and no air conditioning. Oh, man.

Needless to say, we never overpacked like that again.

What we learned:

Avoid overweight charges and overpacked bags at all costs!

Don’t just throw everything into your suitcase and call it a day. Instead, be methodical about what you pack.

Lay everything out and ask yourself one question: “Do I need to bring all of this stuff?” If the answer is no, simply don’t pack it. If you still have room left over after you’ve packed the bare necessities, then go ahead and add in a couple extra items — just don’t go crazy!

2. Lost Luggage

Picture this.

You just endured a 24-hour journey and have finally reached your destination. You’re exhausted and want nothing more than to take a hot shower — and then maybe have a glass of wine.

You head over to the baggage claim and you watch the same bags circle around the carousel for 10 minutes, and fear starts creeping in.

But you hold onto the hope that your bag will appear soon…

20, 30, 45 minutes pass by and finally an airline representative confirms your suspicions. Your luggage is nowhere to be found. And then there’s nothing left to do but leave the airport, luggageless and sad.

Almost every frequent traveler has experienced this. And no, it’s not how they envisioned starting off their holiday.

What we learned:

If possible, ditch checked luggage altogether! Packing light is always the way to go, so if you can make do with only a carry-on bag and small personal item, do it!

But if you do have to check a bag, you should always have travel insurance that’ll cover your lost baggage. If your insurance also reimburses you for purchases of necessary items like clothes and toiletries while you wait for your bag to arrive, then that’s also a major plus!

3. Stolen Valuables

Back in the day, when the iPod touch was the hottest technology on the market, someone stole mine right out of my suitcase in Buenos Aires.

And that was a bummer.

But of course, there was no one to blame but myself. I should’ve paid a lot more attention and taken better care of my things.

Nearly 40 countries later, though, we’ve learned how to ensure our belongings are safe and sound, and we haven’t had an incident since.

What we learned:

When you’re not using them, always, always keep your passports, electronics, jewelry, etc. locked up in your hotel room safe. Even if you think you’re staying in a nice, safe place, don’t leave your valuables’ fate up to chance!

And while you’re out and about, be as inconspicuous as possible. In other words, don’t be flashy with your camera or smart phone, and always keep your guard up.

Despite precautions, things can still go wrong. Having a travel insurance policy that protects your items against theft is always a good idea — especially when traveling to dangerous and/or poor areas.

4. Missing a Flight

This one is still a sore subject for me.

Not too long ago, I missed my flight home to Los Angeles from Munich and had to shell out an extra $600+ when Lufthansa couldn’t rebook another ticket for me.

I’ll make this long sob story short and tell you the quick details.

On the day of our flight home from Munich, I was sick with a fever and chills. So instead of dragging my luggage through snowy streets and dealing with train travel to the airport, I asked my friend if she’d split a cab with me.

But she refused, stated we should just take the train, and promised she’d figure out the way.

I was obviously not in the mood for any of that, so I just said okay. And that was my mistake.

After struggling all the way to the train station through a flurry, she chose the most roundabout train route to get us to the airport. When we finally arrived, the gate had already closed and we were stuck with paying for another night of lodging and another ticket home. Ugh.

What we learned:

Do anything and everything you can to arrive to the airport at least three hours before an international flight.

It’s so much better to be safe (and even bored) waiting for your flight, rather than running late, rushing, and ultimately missing a flight. If anything goes wrong on your way to the airport, such as getting lost or a flat tire, you need that extra buffer.

The other moral of that story is to never leave your fate in someone else’s hands if you can help it! When it comes to getting to the airport on time, just make it happen — even if you’re feeling under the weather like I was. Airfare is expensive as it is, so you don’t ever want to pay double the price!

5. Travel Delays and Not Checking the Flight Status

Another one of the worst mistakes we’ve made when traveling is not checking our flight status right before leaving for the airport.

When we planned to fly from Bali to Singapore, a volcano erupted on neighboring Java and clouded the sky with thick smoke. Our plane was delayed for hours, meanwhile we were stuck watching Netflix in the airport. We could’ve spent at least six more hours enjoying Bali’s beaches, had we checked the flight status.

And worse, was when we didn’t check our flight status when flying from Brussels to Madrid. At the time, airport/airline workers in Paris were on strike, causing flight cancellations throughout Europe. After a taxi fiasco which ended up costing us more than €200, we finally made it to the Brussels airport, only to be rebooked on a flight out of Brussels five days later!

What we learned:

Right before you make your way to the airport, check your flight status. You can never be sure when or why a delay will occur; however, you can be sure that you don’t want to be stuck in the airport for hours, waiting and waiting, when you don’t need to!

Travel insurance can also come in very handy for travel delays.

When your trip has been delayed for many hours, you’re often reimbursed for necessary out-of-pocket expenses like food, accommodation, and transportation!

And trust us, when you’re stuck somewhere for days, like we were in Brussels, this type of coverage is a life saver.

6. Trip Cancellations

When it comes to traveling, there’s almost nothing worse than looking forward to a trip for months, and then having to cancel at the last minute.

The first time I experienced a trip cancellation, a winter storm was the culprit. I was all set to visit Mauricio over President’s Day weekend and Valentine’s Day in New York City, when a huge polar vortex hit the East Coast. And just like that, all flights in and out of JFK were cancelled.

I’ve also been dying to explore Colombia, and last November I thought my wish would finally come true. A friend and I booked our nonrefundable international and domestic flights and our hotels. Then, two weeks before our trip, she had to cancel, due to family reasons. And unfortunately, I didn’t feel comfortable enough to go to Colombia alone, so I didn’t go either.

What we learned:

Sometimes, when unforeseen and unfortunate events occur, you have to cancel a trip you’ve been excited for. But at least, if you have travel insurance, your insurer can reimburse you for unused, prepaid, and nonrefundable trip costs.

If you cancel your trip for a covered reason, travel insurance can at least soften the blow of not getting to enjoy your trip!

7. Getting Injured

What’s traveling without a little adrenaline rush! Right?

Whenever we travel somewhere new, we want to experience everything the destination has to offer — whether that’s multi-day treks in Norway, riding Vespas through Tuscany, rafting over wild rapids in Perú, snowboarding in Utah, or dune buggying in México.

All of these insanely fun activities, though, don’t come without safety risks. If you’re not careful — and sometimes, even if you are — injury, and even death, are possibilities.

But so far, we’ve been lucky enough not to have needed any medical attention while traveling. However, in the event that we do experience an emergency or need to see a doctor abroad, our travel insurance will cover us.

What we learned:

You shouldn’t let the fear of injury keep you from doing what you love! Life is far too short for that.

However, it’s also not a very good idea to engage in dangerous adventure sports abroad without travel insurance.

Having a trip insurance plan that covers you for any medical or dental emergencies, as well as emergency assistance and transportation, will provide you with peace of mind, in the event that something does go wrong.