My Biggest Travel Mistakes

A reader asked me to share my biggest travel mistakes. 

At first, I resisted the idea. After all, the blog’s main goal is to help travelers find unique travel experiences across the globe— and set their trips apart from the ordinary. But then it occurred to me that any of these travel mistakes could make for a memorable trip… for the wrong reasons. So I swallowed my pride and compiled my personal list of top travel mistakes from 20+ years on the road. 

My worst travel mistakes, in no particular order…

Travel Mistake #1 – Underestimating Monkeys

In Costa Rica, I thought it safe to leave the window of my top-floor rental open. While I was out, a capuchin monkey entered the condo. I startled him in the kitchen when I returned. The capuchin bolted to the living room— and frightened himself by lunging toward a mirrored wall. He screamed at his reflection and shat himself. Then he leapt to the curtains and swung, still shitting himself, from window to window seeking the way out. I pointed in the right direction while yelling in English and Spanish. He finally caught on. The management firm kindly sent me to dinner while they cleaned up the mess. Ever since I’ve kept the windows closed. 

Travel Mistake #2 – Being Lax About Safety

A trip to Lima, Peru, taught me the dangers of overpacking and losing my way. A taxi there intentionally dropped me and a friend several blocks from our hotel. We started to lug our oversized, heavy bags in the direction the driver indicated and toward his waiting buddies. Soon we realized we weren’t near our hotel— and the two men were watching and following us. We were clearly tourists, slow-moving, and lost— the perfect targets.

As the pair closed in, we ducked into the nearest shop and explained our predicament. (Once again, I was grateful to speak a second language.) The owner called the hotel for directions and then stepped outside to ensure we got safely underway. Our two “friends” were waiting across the street but departed when they saw the proprietor keeping watch.

Always know the exact address where you’re staying and study the surroundings on a map. Don’t exit your ride until you’re certain where you are. And pack light to remain nimble— you can’t predict when you’ll need to bolt from a bad situation or make a tight connection. Rely solely on carry-on bags and you’ll never worry about lost or delayed luggage, either. On trains and buses, carry-on bags are easier to stow above or below your seat, too, where you can keep a watchful eye on them. 

Travel Mistake #3 – Giving Up My Passport

During my gap year, I entered Venezuela on a tourist visa. To get a job there, I had to apply internally for a work permit. That meant surrendering my passport for two weeks. I didn’t have a choice, but honestly it didn’t concern me at the time. It should have. 

Venezuela had compulsory military service for males. A week after I relinquished my passport, police boarded the train I was on. They made their way from the lead car to the rear, looking for draft dodgers. I knew foreigners were exempt so paid no attention— until I remembered I had no passport. 

So I joined the other young males without papers who jumped off the back of the train as it slowed to enter the station. (Which probably qualifies as another mistake.) They showed me how to avoid the cops by exiting through the tunnel. 

A week later I breathed a huge sigh of relief when the Interior Ministry returned my passport with the requisite visa. I will never surrender my passport again. Without it, I’m at the mercy of local authorities and will have a hard time getting emergency help from the embassy.

Travel Mistake #4 – Rookie Errors

I’ve lumped together here four mistakes common among novice travelers. Remember— sometimes you have to plan for your companions’ mistakes, too, to save yourself  from shared headaches. 

Packing New Shoes

This is a mistake you only make once. I assumed a couple of quick errands around town was enough to break in a new pair of sneakers for a trip to Spain. I was wrong. My itinerary involved a lot of walking, for hours at a stretch. By the end of day 1, I had several painful, open blisters that threatened to keep me off my feet. Blister packs from a local pharmacy saved me. (I wear size 13, so bringing a spare pair of shoes isn’t realistic when packing light.) Now I rely on well-worn shoes— and always bring blister packs, just in case.

Flying With the Flu

I came down with a severe case of the flu two days before flying home from Denmark. Postponing my flight wasn’t an option. But my nose and ears were congested and consequently unable to adjust to the changes in cabin pressure. It was a long, miserable flight home that became excruciatingly painful on the descent.

Although my eardrums didn’t rupture, I had partial hearing loss that lasted many weeks. From then on, I’ve kept decongestants in my backpack— and a pair of specialized earplugs to regulate the pressure in my ears. The earplugs even come with a handy app that signals when to insert them. (Disclosure: This post contains affiliate links. If you click on them and make a qualifying purchase, I may earn a commission at no additional cost to you.)

Food Poisoning

When I lived in Caracas, I often bought lunch from street vendors. Hamburgers with all the fixings— including mayo— were my go-to meal. Until the day I got food poisoning and was the sickest I’ve ever been for a full 24 hours. Now I buy local fare almost exclusively from actual restaurants. If I purchase something on the street, I’m sure to avoid anything with ingredients that could spoil. I never want to be that sick again, especially in the midst of vacation.

Forgetting Noise-Canceling Earplugs

At one time or another we’ve all stayed in hotels with those heavy, slamming doors or noisy, industrial toilets. And most of us know the torture of paper-thin walls and rattling air conditioners. Sometimes the white noise app on my phone just isn’t enough to block it all out. But a bad night’s sleep jeopardizes work presentations and sucks the fun out of vacation. I finally got smart and made disposable foam earplugs a standard item on my packing list. So when I got stuck next to a crying infant on my last work trip, I was the one who slept like a baby. 

Travel Mistake #5 – Too Many People for Too Long

I used to plan, book, and lead groups of high school students on educational trips domestically and overseas. After five years, I concluded the optimum group size is 6-8 students (preferably with two chaperones) for a trip of 7-8 days. Group cohesion and people’s moods deteriorate quickly around day 9.

But after several successful trips using this formula, an administrator asked me to expand the groups to 16-24 people. I mistakenly agreed. The safety, behavioral, emotional, and logistical challenges of herding that many teens through unfamiliar surroundings overseas detracted too much from the experience. Chaperones and students alike suffered, and I would never agree to lead the larger groups again.

Final Thoughts

After traveling hundreds of thousands of miles by plane, train, boat, bus, bicycle, Segway, camel, donkey, and helicopter, I’m lucky I haven’t experienced worse. There are no hard luck stories here about stolen passports, unprotected WiFi hacks (use a VPN!), lost bags, or suffering a medical emergency without travel insurance. I’ve never been arrested or had a mid-flight emergency. But if sharing the misfortunes that have befallen me spares you the same headaches (or a companion’s mistakes), then thank the reader who suggested this post! 

See my blog posts about packing for overseas travel and travel safety tools. And to read how fate and luck spared me from a terrorist attack, click here.