After the pandemic, I finally had the courage to see the world alone. My first solo trip was to Spain—which turned into a whole (mis)adventure of its own. Since then, I’ve learned a lot and was ready for my next big-girl trip: Italy. (Read my (Mis)Adventures in Spain here.)
This trip was extra special because it doubled as my birthday celebration. With more travel wisdom under my belt, I wanted this one to feel easy, fun, and fully me.
Before packing my bags, I started learning Italian—it wasn’t easy at first, but by the time I flew out, I could order food, buy things, and understand directions. Still, despite my preparation, I managed to stumble into some pretty memorable (mis)adventures.
(Mis) adventure #1: Wrong footwear
Even after traveling to Spain, I somehow forgot the number one rule of European trips: comfortable shoes first, cute shoes later.
If you’re packing light, bring one versatile, cushioned pair—trust me, your feet will thank you. I learned the hard way that walking for hours on Italy’s cobblestone streets isn’t fun in minimalist sneakers.
Now, I travel with padded shoes and treat my feet to nightly TLC.
Tip: Break in your shoes before the trip. Your future self will thank you.
(Mis)adventure #2: Forgetting Sunscreen
You’d think a nurse would know better, right? I used to believe my Southeast Asian genes protected me from sunburn. Italy proved me wrong.
By noon, the sun went from gentle to vengeful, and by 2 pm I couldn’t smile without pain.
Lesson learned: the sun isn’t picky.
Notice the awkward smiles. My lips got swollen from the excessive sun exposure. Never again, lol!
Tip: Always pack sunscreen and SPF lip balm.
(Mis)adventure #3: Trying Too Hard to Fit In
Before my trip, I studied Italian culture, fashion, and etiquette– then overdid it.
That’s how I ended up looking like a lost extra from a Renaissance play. One day I wore a top that made me look like a trying-hard medieval painter; another I squeezed into a dress so unflattering that I refused to take pictures altogether. One outfit even ripped on the train–proof that the universe humbles you when you get too confident!
Beyond the wardrobe fiascos, I also filled my itinerary with attractions that were “highly recommended” even though they weren’t really my thing. I tried to dress, eat, and act like a local–even though no amount of Italian vocabulary could disguise my wide-eyed tourist energy.
The result? I felt uncomfortable and out of place, all because I was chasing an image of what I thought traveling should look like.
Lesson learned: You don’t have to fit in to belong. Listen to advice, yes, but always make space for your own preferences, pace, and personality. Traveling isn’t about imitation; it’s about exploration.
(Mis)adventure #4: Not Trying Enough Street Food
Sure, I devoured my share of pizza, pasta, tiramisu, and gelato, but I regret not exploring more of Italy’s street-food scene.
Here are a few favorites that I did try:
First is this snack that I ate in Verona called Arancino–crispy rice balls filled with mozzarella.
Next are the ever-famous cannoli— bite-sized heaven in lemon and chocolate.
Sfogliatelle are these flaky pastries with sweet, creamy filling. Similar to the cornetto (“Italian croissant”), but lighter and, in my opinion, less flaky. The variant I tried had powdered sugar dusted on top.
Below is a humble cup of strawberries with Nutella and whipped cream. Nothing spectacular, but I loved it! It’s not something I eat often, so the novelty was very much welcome.
Bombolone are Italy’s answer to donuts, only better.
And of course, you’ll never go wrong with a cornetto and a cappuccino in the morning:
Still, I missed local gems like maritozzo and tartufo. Well, that’s reason enough to go back!
(Mis) adventure #5: Forgetting a Boredom Buster
Long train rides look romantic—until your phone dies mid-trip. On my Milan-to-Rome ride, I spent an hour staring at strangers, wishing I’d brought a book or downloaded a show.
So my advice to my fellow travelers/wonderers: make sure to bring a little “boredom buster”, may it be a book, a series, a puzzle book, to kill the time. Especially in Europe, where train schedules may be unpredictable.
Lesson learned: pack something to keep you entertained. Trains get delayed; boredom is real. A small distration can save your sanity.
Final Thoughts
Italy was beautiful, unpredictable, and unforgettable. My mistakes turned into lessons, and my lessons turned into stories.
No matter how seasoned a traveler you become, (mis)adventures are inevitable—and they make every trip richer.
Here’s to more laughter, more learning, and more beautiful mistakes along the way.
Arrivederci, fellow wonderers!
Snapshots From My Birthday Trip to Italy
