Here are some of the worst, stupidest, silliest, and most embarrassing traveling mistakes I've ever made. From inconveniences to horrors, these stories were total nightmares at the time, but have now gracefully aged into jokes. So go ahead, laugh at my pain, and learn from my blunders.
"The only people who ever get anyplace interesting are the people who get lost."
the horrific rideshare to nowhere
Once upon a time, in Italy, I tried out a rideshare called BlaBlaCar. I booked one bound for Geneva with some lovely French people who didn't speak any English. And I didn't speak enough French. So I occupied myself on the ride by staring out the window and checking the map on my phone.
But I wasn't paying attention to the fact that I was burning data like nobody's business and I also was running out of battery simultaneously. I was in the red zone. The danger zone. And no usb car charger. It was the Twilight Zone.
So, we're trying to communicate with Google Translate but limited cell service made it utter nonsense. Then they randomly decide where the drop-off point is going to be and I, of course, assume that since I paid for this service to drop me off in Geneva, that's where it'll be. Well, no.
Turns out it was a random spot on the side of the highway in France. Not only the wrong city, the wrong country. On a Sunday. On a holiday. A government holiday. No buses were running. Luckily one of the other stranded passengers got us a ride that took us around the border of Switzerland and dropped us off in a small southern village. I then had to maneuver all the way north to Geneva with no maps, no cash, and an appalling lack of French fluency. Unable to purchase tickets, I was fortunately helped by a couple good samaritan tram drivers that let me ride for free and helped me get where I needed to go.
Last. Rideshare. Ever.
the intimidating almost arrest
One morning, on the west coast of Mexico, while doing a u-turn on a very rural street in a very rural town, my friend and I skimmed a sand pile in the road in our rental car. Our expensive rental car. We slowed down and poked our heads out the window to see what sand to drive on. And this behavior attracted some attention. The attention of an elaborate scam.
Enter the Mexican Shakedown. The police showed up in SUVs with full combat gear. They detained and surrounded us with the guns. Big guns. Lots of big guns. They said they were taking our car to be impounded, that we were going straight to jail, and that we'd never be allowed to leave the country, and lots more scary things.
But then, we're told we don't have to go all the way to the courthouse, because it turns out that these super kind police officers are willing to negotiate an agreement right here on the side of the road so that we can just go on our merry way.
I knew it was a scam as it was happening. There's no crime, no ticket, no infraction, no paperwork, no nothing. But that really doesn't help much when you have a dozen guns pointed at you from a bunch of guys in military uniforms yelling at you in Spanish. So we forked over the cash. Ran away from the scary men with the guns. Jumped in the car. And high-tailed it out of there as fast as possible.
"You won't find reasonable men on the tops of tall mountains."
the three circles of couchsurfing hell
Early on in my full-time travel days, everyone kept telling me I've got to try Couchsurfing. Sign up to the website, they said. It's a great community, they said. It's so safe and fun, they said. So, one time in Holland, I decide to put aside my extreme skepticism and try it with the most open mind I could muster. If everyone loves it, it must have it's good points, right?
I was prepared to entertain my host as best I could with stories so that they felt the exchange was a fair one. However, I may have bit a bit naively prepared for the expected intimacy. Was it just me or was this what actual Couchsurfing really was? And if so, why does everyone pretend otherwise? Like it's just a community of platonic friends all holding hands, singing Kumbaya, and doing the world a kindness out of the goodness of their hearts? As if.
I had to know. So I tried it out a second time. And, a third. You know, for science. Each time escalated exponentially. The last and final time, when I didn't want to take a day trip with the host, he flipped out, raising his voice, cursing at me, calling me all kinds of names, and kicked me out of his house. As I was throwing my stuff in my bag and heading out the door, he was yelling down the street about what a burden I was because I used a bath towel that he now had to wash.
That was my last and final experience with the fake ass hippie Couchsurfing community. Just like the bumper sticker says, "Gas, grass or ass. Nobody rides for free." Couchsurfing is, of course, not at all free, and exactly as dangerous as it sounds. You always have to sing for your supper.
the endless journey to almost paradise
Way back in the day, before I created my checklist of things to do before travel, like download maps and check data, I was taking a journey between a few towns along the Italian coastline. I was in a rush to get going on this particular occasion so let's just say I probably wasn't totally prepared.
I took a train from Genoa to a lovely little town near the Cinque Terre called Bonassola, on my way to visit a beautiful resort on the coast called La Francesa. It was some sort of holiday, the buses weren't running, and there were no taxis around. So I knew I had a good hour walk ahead of me to get from the town I was in all the way down to the coast.
An hour walk would've been a pleasure, had it not been for two omens of impending doom on this day. One - This walk will be uphill. The whole way. Up a windy, twisty, hilly road with one lane and no safe place for a pedestrian to walk. A some 200 meter incline. Great. And two - Are those rainclouds? Yep. Instant rainstorm. Pouring rain. The whole way.
I survive the journey and arrive in a puddle, to get good and bad news. The good news is, although they've closed up early for the holiday, they've kindly left me a key to get in. The bad news is, the restaurants and shops have also closed, so there's no food. And I'm too far away from any nearby town, too tired, and too wet to put forth any stuggle, so although I have a million dollar view of the sea, all I have is a teeny tiny bag of crackers and a glass of water to enjoy it with.
"To shut your eyes is to travel."
the great boarding embarrassment
Another torrid tale due to not checking visa rules meticulously enough, I once booked a flight plan directly with an airline that put me into a brief layover in another country. The visa rules and lengths of stay for that country were different according to method of transportation, such as arriving by air versus arriving by land.
I somehow mixed up this technicality in my travel planning, and this layover would've had me in the country over my allowed transit time, which is definitely not a minor detail when it comes to immigration.
Airlines are usually very proficient in picking up discrepancies like this one when you check in at the counter to get your boarding pass and do your doc check. In fact, the entire point of the document check is to prevent idiots like me from making stupid mistakes just like this.
But this airline didn't catch this at checkin, so I waited several hours to board, walked up in line with everyone else, and handed my boarding pass over. But that's as far as I got, because that's when it was caught. So I couldn't board the flight, I had to exit the airport, get a hotel, rebook my flight plan, and do the whole thing over again the next day... successfully.
the online shopping scare
The reason you should always submit your travel notice to your bank is to avoid credit cards scares like the one I had. Once I submitted a travel notice, threw a few countries in there, guesstimated some dates, and pretty much forgot about it.
Until it reminded me. I didn't know my travel plans when I made it, and had since extended travel past the dates I entered, so my travel notice wasn't even valid anymore. One day I placed an order for online groceries, it went through just fine, I got a confirmation and a delivery date and all was well with the world. Food was on its way.
Sometime during the middle of the night (also known as normal banking hours in the Eastern Time Zone), I missed a call from an unknown number. I don't really use my phone for calls, or keep it near me, so it was not alarming. Until it was.
When I got up the next day, there was a voicemail from Visa Fraud, who thought my online shopping may have been a fraudulent charge. I called them back, waiting nervously in a queue for what seemed like forever, and straightened it out. But I did it just in the nick of time, because they would've cancelled my card and prevented me from accessing my money. One single missed call could've turned into a major catastrophe for me on the other side of the world.
Living the dream.
the exasperating glass entrapment
I used to use the hub of London as an easy travel stop and a convenient way to head to Brighton. But I've started to avoid flying into London because of the insanely grueling immigration questions and the far too frequent detainment just for trying to get a tourist visa, even for a layover.
The sheer amount of time I spent in the glass box of shame at Gatwick was starting to take years off my life. It took hours, at the very least. Even with all the proper travel preparation, such as proof of onward travel, insurance, income, and accommodation, they still hate having us visit. Every single time I'm in detainment, everyone else in there is American too, and we are all detained for the most trivial of reasons, even if they don't make any sense.
As a full-time traveler of 5+ years and counting, I am bloody well aware how darn much Brits hate Americans, but the intensity was eventually made as clear as the glass detainment box I was sitting in. So, I gathered my favorite UK visa rules I've been told, and the best is we are just not welcome. Maybe they should add that to the stamp.
"All of life is a foreign country."
the midnight check-in nightmare
Once upon a midnight dreary, while I wandered weak and weary... I again arrived into a new airport, country, city, and hotel. This time it was Israel. It was past midnight, and I took a taxi to the hotel I had booked on my fav booking site.
In my travel flurry, I did not read the fine print of this particular booking. If I had, I would've known that this hotel didn't have an on-site reception and that the only way to check-in to your room was to call another location and have someone come over and meet you at the property. This snafu was compounded by my second mistake, which was not topping off data to make cellular calls. Awesome.
So I'm dropped off, and left alone, by the only soul around, in the dark, in the middle of the night, tired and exhausted, to an empty hotel where nobody works and the door is padlocked. And I can't call the person to come meet me. I'm also in a residential neighborhood where there aren't any business or restaurants. And of course I can't speak the language.
So I have no choice but to take off on an indeterminate hike walking until I can find the first open bar, stop in and try to use their phone. An hour later, the crisis was averted with cold beer and a new friend with a working cell phone, and I finally got the keys to a good night's sleep.
Do not disturb.
"What matters most is how well you walk through the fire."
the scandalous delivery saga
When your bank card expires, you need a new one. Easy enough in your home country, at your billing address, in your language. Not so much halfway around the world. Mine wouldn’t ship internationally so my plan was to send it to a friend to send it to me. Then one simple plan became months of annoyance spanning several countries.
I began trying to send it to Singapore, but my bank delayed shipping by two weeks and it took two extra weeks to arrive. Then I moved to Indonesia, but the house had no address. I tried to get it sent locally, but FedEx was far away, UPS didn’t know geography, and DHL wasn't sure their office existed. I moved to another country, Thailand. The card was sent. I tracked it until it was declared delivered, but wasn't. When I reported it lost, I was told they can ship internationally. Oh, joy.
The second attempt ended in a non-delivery saying customer unavailable and went into a bizarre undeliverable status before being returned. On the third, the same thing happened. I began to believe expat stories that delivery only happens with a bribe. Again I moved, to Hong Kong. On the fourth, they wouldn’t come to my door because of stairs. On the fifth, as soon as I saw the 'out for delivery' tracking status, I ran outside, waited 3 hours, and threw myself on top of the approaching van.
A week later I got an email that my first letter (sent priority international, signature required, guaranteed delivery in 5 days) was inexplicably delivered, 4 weeks late, to some rando at the building office at the last address in the last country.
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