My first night alone in Italy, I wandered the streets for over an hour—not because I was lost, but because I was terrified to eat dinner by myself.
I had booked a 9-day solo trip through northern Italy. I was nervous, but mostly about logistics: navigating trains, staying safe, and communicating in a foreign country. As someone who’s 82% introverted on the Myers-Briggs scale, I figured I’d have no trouble spending time alone.
And I wasn’t wrong—but I also wasn’t prepared for the unexpected emotional challenges that came with solo travel.
If you’re planning a solo trip—especially as an introverted woman—save this article. Here are the tough moments I faced and how I worked through them.
Eating Alone
Eating alone was surprisingly hard—especially at dinner.
I remember walking the streets of Italy on my first night, feeling so insecure about where to go and what others would think of me. I ended up at a pizza restaurant surrounded by couples and friend groups. I felt exposed.
But eating alone wasn’t the real challenge—my insecurity was. I was so worried about being judged that I almost couldn’t enjoy the meal.
So I looked around. No one was paying attention to me. Everyone was focused on their own evening.
That realization allowed me to breathe. I opened my Kindle, soaked in the mountain air, and practiced being content in my own presence.
I felt this way several more times during the trip, but I kept reminding myself: no one is thinking about you as much as you are. And when I stopped worrying, I could finally enjoy the moment.
Making a Plan (As a Type B Traveler)
As a Type B person, planning isn’t exactly second nature.
My Italy itinerary included flights and places to sleep—nothing more. Every day, I had to decide what to do, where to go, and how to get there.
At times, I wished someone else could just make decisions for me. But solo travel forces you to choose—and that’s where growth happens.
Eventually, I realized that this freedom was a gift. I could follow whatever path I wanted. I just had to be bold enough to choose it.
Decision Fatigue Is Real
When you travel with other people, you share the decision-making. When you travel solo, every choice is yours alone:
- What to eat
- Where to explore
- When to move
- What’s “worth it”
I found myself constantly questioning: Am I missing something better? What would other travelers choose?
But here’s what I discovered: the best experiences weren’t the most popular ones. They were the quiet, spontaneous moments that couldn’t be planned:
- Eating gelato in a silent Venetian alley
- Watching a gondolier tie up for the night
- Hearing the soft splash of the canal with a violin playing nearby
- Sharing an Aperol spritz with a local in Vicenza who told me about his son studying in the U.S.
These weren’t on my bucket list—but they’re the ones I’ll remember forever.
Dealing with Creepy Men—and Being Protected
Before my trip, I worried about being followed or targeted.
But what I didn’t expect was how quickly strangers stepped in to protect me.
On a train, a man began harassing a woman sitting near me. Two nearby passengers immediately welcomed her to sit with them—and gestured for me to join, too. The man tried to intimidate us, but we were now a group.
That moment taught me that kindness is everywhere, and that people—especially women—look out for each other, no matter the language or culture.
Getting on the Wrong Train
Yes, I got on the wrong train. It skipped my stop, and I was charged extra.
But instead of panicking, I asked for help—and people helped me. Train station staff were kind. Travelers offered guidance. A custodian even pointed me in the right direction.
Lesson learned: just ask. Most people are happy to help someone who’s lost.
Final Thoughts
Solo travel can be intimidating—but it’s also transformative.
It forces you to sit with discomfort, to navigate fear, and to learn who you really are when no one’s around to reassure you.
It also invites connection, adventure, and the kind of quiet joy that only solitude can bring.
If you’ve ever considered a solo trip, I hope you’ll take the leap.
It might feel uncomfortable at first—but I promise, it’s worth it.
Hi, I’m Olivia. I’m a freelance writer and blogger. I write about travel, humanity, and anything I’m curious about. Follow along on this blog for more budget-friendly travel tips, stories, and reflections!
The Olive Atlas 
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