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The Biggest Travel Fails & Triumphs from a Year-Long Adventure

Long-term travel isn’t just a series of picture-perfect moments; it’s a mosaic of misadventures, learning curves, and unexpected victories. My year-long round-the-world trip was filled with both lows and highs, each one teaching me invaluable lessons about resilience and adaptability. If you’ve ever wanted to peel back the curtain on long-term travel and see some of things Instagram influencers won’t show you… here’s the deep dive on my worst travel fails and my best travel triumphs!

Table of Contents

My Worst Disasters & Travel Fails

solo female traveler in front of a flower mural

Losing Half My Packing List

The early months of my trip were regularly punctuated by items disappearing from my backpack, starting from day one when I left behind my everyday black cardigan. As trivial as it sounds, this simple thing sent me spiraling. It was just so jarring that I couldn’t make it even one day into my trip before making a mistake. Over time though, things breaking or getting left behind either happened less frequently or simply didn’t bother me as much. I developed a much healthier attitude towards the importance of stuff and the reality that these kinds of things happen.

Read my full melodramatic musings on day one of my trip here.

The Taj Mahal Excursion That Wasn’t

My failure to see the Taj Mahal wasn’t just a missed tourist opportunity; it was a harsh lesson in the effects of politics on personal plans. Caught in an unexpected national economic crisis, my plans crumbled, leaving me to grapple with feelings of frustration and helplessness. This experience underscored the importance of letting plans go, but it also taught me a lot about what things are in our control and which things aren’t. In my case, there were big political and economic forces that affected my travels in India, but I also took some bad advice and if I had planned my trip better, I might have had a better experience.

Read the full story about how I missed seeing the Taj Mahal here.

travelers rushing through an airport

Missed Flight Across Continents

I had a carefully crafted itinerary using frequent flier miles to get from Japan to Uruguay for just $300 in fees. It was a beast of a travel jag, covering several connecting flights over multiple days. And then I got on the wrong train in Tokyo! I’d gone about 45 minutes in the wrong direction before realizing my mistake. There was no way I was going to make the flight on time and as an added bonus, my phone was on about 2% battery. It was a stark lesson in the domino effect one mistake can have on the bigger picture. But it was also a lesson in the importance of staying composed under pressure. I had to simply do what I could to get back on track. Fortunately, the airport staff at Narita was so kind and helpful, and when I called the airline’s customer service line, I was able to fix my itinerary and salvage my miles!

I did finally make it to Montevideo. Read here about whether this often overlooked South American city is worth a visit!

Booking a Stay in an Unsafe Area

Booking an Airbnb in a questionable neighborhood without Wi-Fi was a sobering wake-up call to the dangers of complacency. And I definitely got complacent at a stage of my trip… dare I say, even cocky? After months in places like Bali, Japan, and Uruguay, I was no longer being diligent about my safety as a solo female traveler. Arriving in Buenos Aires taught me the hard way about the importance of thorough pre-trip research and the wisdom of always having a backup plan.

Read more about this misadventure and my advice for finding safe neighborhoods for solo female travelers.

solo female traveler completing the Inca Trail to Machu Picchu

My Biggest Travel Triumphs

Re-routing My European Travels

I had originally planned to spend a month in Istanbul. Two terrorist attacks and an attempted military coup later, this seemed like a bad idea. Fortunately, I know how to pace my travels so I had time built into my plans to manage my itinerary! I spent a day hunkered down in my Italian hostel reconfiguring my itinerary to spend more time traveling overland in the Balkans and enjoy a month in London instead. I felt so proud of how adaptable I was, how quickly I could pull together a complex itinerary, and fully cemented the importance of Admin Days.

Read more about Admin Days and why you need them.

Surviving Two Mountain Treks

I’ve grown fond of saying I’m not outdoorsy, I’m outsidey. (Kudos to whatever TikToker turned me on to this phrase.) Completing multi-day treks in Nepal and Peru was a monumental achievement that pushed me to my physical and emotional limits.

Read more about the Annapurna Sanctuary in Nepal or about the Inca Trail in Peru.

view over South America from a plane

Packing in 45 Minutes Flat to Return Home

That’s right — in less than an hour, I went from being on my way to tango class in Buenos Aires to being on my way to airport to hold vigil at my grandfather’s death bed. There’s a practical side to this achievement. It felt like quite the feat to re-assemble my backpack so quickly! But there was an emotional component too: I have never been more certain I was doing the right thing. Understanding your core values helps you find success and fulfillment in your travels. It’s one of the first things I do with my students inside Round-the-World Roadmap.

Continuing After a Family Loss

While it was 100% the right thing for me to be with my family for my grandfather’s death and funeral, I’m also incredibly proud of myself for not ending my travels there. That Inca Trail trek I mentioned earlier was both my most anticipated bucket list item and one of the best experiences from my entire year of travel, and I didn’t want to cancel it over a personal loss. Reconfiguring my plans in such a massive way was the ultimate triumph and a surprisingly satisfying capstone to my year-long adventure.

solo female traveler in Mostar Bosnia and Herzegovina

Have you noticed a theme? My travel fails were mostly times I handled change poorly, and my triumphs were mostly times I handled change well. How you handle challenges and adversity is one of the biggest signs whether long-term travel is right for you.

If you’re contemplating long-term travel, but not sure whether you’re ready for this kind of adventure, let’s chat! Book an Explore Call with me, and together, we’ll turn your travel dreams into a plan for adventure, growth, and some unforgettable travel triumphs of your own.

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