Overpacking Misadventures of a First-Time Traveler
This is what happens when you have zero travel experience and twenty-four hours to prepare for your first overseas trip.
Hey friends!
Before we jump into the story, I want to let you know about a few happenings I’m excited about!
First, I’m working on a new website that brings together all the various elements of exploration -- travel, creativity, lifestyle, personal development, etc. It feels expansive and exciting to create a space where I can continue to share my love of travel, while also incorporating other creative projects and more of what it means to live like an explorer.
Second, I want to share a couple of cool events that I’ll be attending as a speaker and contributor over the next few months!
Bougie in a Backpack Travel Summit - I’m super pumped about this! It’s a free online event all about traveling the world without breaking the bank. You know that’s my jam.
The Everything Conference - This conference was a game-changer for me when I went in 2019. If you’re a multi-passionate human who can’t stand the idea of doing just one thing, this one is for you. These are your people and we’d love to see you in Minneapolis this August!
Alright, since there was a tie in the last poll, I’ve chosen to share one of my more embarrassing travel misadventures from that first overseas trip I wrote about last time. In the next standard issue, I’ll share the other story from the tie. Then we’ll get back to the polls.
Misadventures of a First-Time Traveler pt. 1
After a week in Sweden and a few days in Germany, with no major issues, I felt like I was starting to get the hang of the whole European travel thing. Then I went to Thiers, a little town in Eastern France.
I strode confidently out of the Clermont-Ferrand airport and looked around for a taxi to take me to my hotel. A portly, grey-haired driver waved me over to his cab. I towered over him by at least six inches (I’m about 5’9” -- tall, but not that tall), but what he lacked in height, he made up for in girth and gruffness.
Together, we maneuvered my baby elephant-sized silver suitcase into the trunk of the little Peugeot, where it took up nearly all of the available space. Though my luggage hadn’t increased in size during the ten days I’d been traveling, it certainly had put on a few pounds. I’d been happily gathering trinkets from cheesy souvenir shops as reminders of this wild adventure, plus I’d picked up two big ceramic beer steins for my mom’s collection. Then there were the books…
I’d finished the book I’d brought from home within the first few days. The train station bookshop in Stockholm had a section in English. The Twilight series was all the rage at the time, so I picked up the first book, curious to see what the fuss was about. Also, it was over five hundred pages, so I figured it would keep me occupied for a while.
Before I go further, you need to understand my relationship with books. I was in love with them before I could even read! As an only child, books provided constant friends and worlds to explore. My fondness has remained constant over the decades, and the idea of giving them away after I’d finished felt like discarding a cherished loved one. (I’m better about this now!)
By the time I returned to Stockholm a few days later, I'd already finished the first book. It was like junk food for my overstimulated brain, which was constantly processing piles of new information on this whirlwind trip. I stopped in at the same bookshop and bought the other three books. As a collection, they probably weighed nearly ten pounds.
By the time I arrived in France, my monstrous suitcase was not only ridiculously awkward in size, but it was also pushing fifty pounds. When we pulled up in front of a little hotel that looked like it had been around for at least a few hundred years, the driver made it clear that he intended to help with my luggage. I tried to wave him off, but he was insistent. We hoisted the suitcase out of the trunk and he rolled it smoothly into the lobby. I hoped that would be the end of it.

After checking in, I looked around for the elevator but only saw a narrow staircase. To my horror, the driver started wheeling the suitcase toward the stairs, clearly intending to take it up to my door. I wasn’t sure he would fit in the stairwell by himself, let alone with my suitcase, which was about half his height! I grabbed for the handle to take over, but he was a stubborn old goat.
His eyes bulged as he attempted to lift the suitcase, and he shot me a look, suddenly understanding why I hadn’t wanted his help. Now, his pride was at stake. I stood at the bottom of the stairs, absolutely mortified and wishing the floor would swallow me up as I watched him struggle up the tiny staircase. All I could do was prepare myself to give him the best tip he’d ever received.
From where I was standing, it really did look like he was trying to wrestle an unwieldy baby elephant into submission. However, his determination and pride carried the day. It felt like an eternity had passed by the time he dropped the luggage in front of my door, shaking the entire building like an earthquake.
Red-faced and huffing, he came back down the stairs triumphant. I proceeded to hand over a tip equal to the entire fare for the thirty-minute ride from the airport. I hoped the generous tip would serve as redemption and earn me a bit of kindness in the story he was sure to tell his fellow cab drivers about the silly American lady and her ridiculous suitcase.
After an embarrassed wave goodbye, I climbed the narrow staircase to my room. When I opened the door, I discovered I was staying in a space about the size of a small walk-in closet. There was no amount of empty floor space large enough to even open my unwieldy suitcase.
Every time I needed to access any of my things, I had to wrestle the damn thing onto the bed in order to fold it open. Of course, every time I took something out, I forgot another item I needed so I had to do the dance all over again. It only took a couple of rounds before I swore to reform my over-packing ways. To this day, every time I pause to ponder whether or not I really need to take an item with me on a trip, I think back to that day and usually leave the item in question behind.
Oh lord, I’m sure my face still flushes red with embarrassment when I tell that story! Talk about a learning experience! 🤪
Have you ever had a mortifying misadventure while on the road? If you feel like sharing, I’d love to hear it! Shoot me an email and tell me all about it -- I’d love to feature it in a future issue, if that’s something you’re open to. We can totally keep it anonymous too. 😉
Do you want to hear more misadventure stories? I have one more from this trip that’s far more embarrassing than this one! I guess I’m ready to share them all, if it will give you a good laugh! 🤷♀️
If you have suggestions about other stories or topics you’d like to hear about or want to share your feedback, you can use this form! You’re always welcome to leave comments on Substack as well.
Until next time. Adventure on, my friends!
Cheers,
Annie
I really enjoyed this and, yes!, would love to hear more misadventures!