Travel Lessons I Learned the Hard Way

No matter how much I travel, I still make mistakes. Some are minor—missteps that make for funny stories later. Others serve as sharp reminders that even the most experienced travelers can be caught off guard.

Looking back, there are a handful of mistakes that stand out—not just for the inconvenience they caused, but for the lessons they taught me. Each one made me a smarter traveler. And if sharing them helps someone else avoid the same pitfalls, even better.

Mistake #1 - Peru: The flight home that wasn’t

The artsy neighborhood of Miraflores is a fun place to explore in Lima.

After a two-week trip in Peru that included hiking part of the Inca Trail to Machu Picchu, I was exhausted and more than ready to go home. Flights from Lima to the US generally leave at night, and mine was no exception. As soon as I boarded at 11 p.m., I popped two Tylenol PM, pulled down my eye mask, and prepared to sleep all the way to Miami.

But the plane did not take off. I was in a deep sleep when the captain came on and announced that due to a mechanical failure, the flight had been canceled. We’d need to deplane and rebook.

As the other passengers grabbed their carry-ons and sprinted off the plane, I blinked groggily, feeling like I was at the bottom of a well. I slowly gathered my things and stumbled in a daze out of the plane to the gate—where I ended up the very last person in line to rebook and well behind all the folks who snagged the open seats on the only other US-bound flight that night. I was so out of it (and the WiFi in the airport so bad) I couldn’t even use the internet to rebook.

And that’s how I ended up spending an extra 27 hours in Lima.

Now, if I take any sleep aids on a plane, I do it after we’re safely in the air, just in case.

Mistake #2: - London: Stranger on the train

Even when all dolled up, London still requires travelers to be aware.

I know London like the back of my hand, but one quiet evening on a subway platform, I made a simple mistake—one that almost cost me more than just a delayed journey.

The train was late, and as I absentmindedly studied the Tube map, a man approached me. He was about my age, British, and carried an umbrella. He smiled and asked if I needed directions. I shook my head, politely declining, but he kept chatting—asking where I was from, whether it was my first time in London. As a solo female traveler, I'm always cautious about sharing personal details, but he seemed friendly enough, and I like to trust people.

The Tube arrived, and he followed me onto the train. He sat with a seat between us—respectful, but persistent. Then he dropped a strange detail: he said he worked for the American Embassy, tasked with preventing terrorist threats. That was my first red flag. If he really had a job like that, why would he announce it so casually to a stranger on the train?

Then came the second red flag: he mentioned his long journey home, and I suddenly realized we were traveling in the opposite direction from his supposed destination—something I only knew because of my familiarity with the city. My stomach tightened. There might have been a reasonable explanation, but my instincts screamed otherwise.

At the next stop, I jumped up just as the doors were about to close, saying, “Oh, this is my stop,” and dashed out. My heart pounded as I ducked around a corner, watching the train pull away.

For a moment, I wondered if I was being paranoid. Had I made a big deal out of nothing? Then, after a few moments of waiting, I cautiously stepped back onto the platform—only to freeze. There he was, sitting on a bench, waiting for the next train. He wasn't supposed to be there. If he had truly just realized he was on the wrong train, he would have left the station altogether. But he hadn't. Instead, he was lingering, scanning the platform.

I slipped back out of sight, my pulse racing, as an announcement crackled over the loudspeaker: “Pickpockets are known to be active in this station. Please be aware of your possessions.”

I felt both stupid and validated. The only reason that man had gotten off the train was because he was looking for his next target—whether to steal a wallet or do something much worse. That target could have been me.

I had trusted my instincts, but I had made myself an easy mark by looking at that map. And I’d assumed that because I felt safe in London, the city was safe. I’d forgotten that awareness is just as important as confidence—and that when something feels off, it probably is.

Mistake #3 - Shanghai: The one thing you should never check

I still don't know what was in this dish.

I used my award points to fly business class from Shanghai to Sydney and was eager to experience the much-hyped in-flight dining other travelers had raved about. When my meal arrived—a beautifully arranged selection that included a raw fish salad—I dug in happily.

Minutes later, my throat tightened. Hives erupted across my wrists.

My breathing was fine, so it seemed like a mild allergic reaction, but the discomfort was immediate. Instinctively, I reached for the emergency Benadryl I always carried while traveling, only to realize it wasn’t there. My first aid kit was in my checked luggage.

I knew better. It’s a cardinal rule never to check medications, and I always kept my daily prescriptions in my carry-on. But I’d never thought to keep my first aid kit handy on the plane. I started carrying one after getting COVID-19 in Egypt, where finding reliable medication was a challenge. It was a compact pouch with a thermometer, Tylenol, emergency antibiotics, anti-itch cream, traveler’s diarrhea meds—and, of course, Benadryl. Now, that pouch was buried somewhere in the belly of the plane.

For the next two hours, I itched and worried as the hives spread from my wrists to my elbows. Fortunately, the angry welts eventually began to fade, and by the time I landed in Sydney eight hours later, they were gone.

That was the last time I checked my allergy meds on a plane—and, for that matter, the last time I ate raw fish at 35,000 feet.

Mistake #4 - Melbourne: When cozy nights turn into survival mode

Was this adorable kangaroo as cold as I was?

July is not the best time to visit most of Australia. That’s winter in the Southern Hemisphere. But I had three weeks off, I’m a hearty New Englander, and I figured I’d be just fine. Famous last words.

I had planned to drive the Great Ocean Road, soaking in the rugged coastline, scenic vineyards, and seeing as many kangaroos and koalas as possible. I even booked an adorable Airbnb on the edge of a vineyard, picturing cozy evenings sipping wine while wrapped in a warm blanket. What I got instead was an icebox.

I arrived during a wicked rainstorm, tired from a long day of travel, only to discover something I had not researched ahead of time: homes in Australia are often not insulated.

Let me paint the picture. It was 48 degrees Fahrenheit (9 degrees Celsius) inside when I walked in—colder than the actual outside temperature. The only heating came from a tiny wall-mounted heater, the size of a toaster, which, even at full blast, barely threw off enough warmth to thaw a popsicle. There were no extra blankets. No carpets. Just cold, bare floors and walls that did nothing to trap heat. Within minutes, I could see my breath inside the bathroom.

At first, I told myself it would be fine. I’d layer up. I’d make do. It was too dark and stormy to find another place to stay. But by the time I went to bed, I was wearing every piece of clothing I had packed, including my winter coat, and I was still shivering. I didn’t sleep so much as shut down for a few hours, waiting for morning. As soon as the sun rose, I grabbed my bags and bolted.

But here’s the kicker: when I stopped at McDonald’s the next morning to warm up, it was just as freezing. That’s when it hit me: this hadn’t been just a bad Airbnb. This was a thing. Australian homes, restaurants, even public spaces are not heated the way I expected.

I had completely underestimated how cold it would feel and assumed indoor spaces would be warm. But 50 degrees in New England feels completely different than 50 degrees in Australia when there’s no insulation, no central heating, and damp winter air creeping into every crack. And New England winters come with heated buildings, warm cafes, and cozy cabins—none of which I found in rural Australia.

I still had an amazing trip, but that first night? Absolutely brutal. Now, whenever I travel somewhere new, I don’t just check the weather—I check how people live with that weather. And I pack accordingly. Lesson learned.

Mistake #5 - Japan: Lost in translation (literally)

Still not sure what was in this dish with the noodles and tempura.

A few years ago, I took a spontaneous trip to Japan. It wasn't my first time traveling abroad, and Japan had long been on my list of places to visit. So when I had an unexpected three weeks off, I booked the trip without hesitation—and without my usual thorough research. That was my first mistake.

I had always thought of Japan as an accessible destination for a first-time traveler to Asia. My father had traveled to Japan frequently for work and loved it. English is the global language of business and tourism, and I'd been to four continents without fluency in the local languages, so I figured I'd be fine.

I was wrong.

From the moment I landed, I was thrown by how little English was spoken and how few signs were in English. I knew exactly two words of Japanese—hello and thank you—and quickly discovered that wasn't going to cut it. While English is taught in Japanese schools, I hadn't realized that many people are culturally reluctant to speak it unless they feel completely confident. So even when I asked for help, many people were too self-conscious to try.

It was a wake-up call. I had made a classic ignorant traveler's mistake: assuming that because a country is modern and well-visited, it must be easy to navigate without preparation. I hadn't downloaded Google Translate. I hadn't learned basic phrases beyond greetings. I hadn't even researched how to use the subway system properly, which left me fumbling through confusing, half-translated conversations. Even ordering food was a challenge—I once ordered ramen expecting chicken but got something I still can't identify. Luckily, it was delicious.

I spent much of my trip frustrated—not with Japan, but with myself. Even in a globalized world, language barriers are real. A little research would have made an enormous difference. I had underestimated just how different Asia is from the West, and I paid for that oversight with confusion and unnecessary stress. It was a good reminder not to assume English will be widely spoken.

In the end, I still had an amazing trip, but Japan humbled me. It reminded me that no matter how experienced a traveler you are, overconfidence can trip you up just as much as inexperience.

Next time, I'll be ready.