How I found comfort as an anxious traveller on a solo trip to Italy

July 12, 2023

A few months before my 30th birthday, I had my own 13 Going on 30 moment. I wasn’t a gawky teenager wishing on a sack of stardust for curves and cool friends or anything, but just like young Jenna Rink, I made a wish—and a solid plan—to shake up my life.

At the end of 2017, I was going through a sad-girl December—bored, restless, and already entrenched in my annual bout of Seasonal Affective Disorder. My forecast looked something like this: 30, (kinda, sorta) flirty, and (not really) thriving. Over the holidays, I decided to take a birthday sojourn to Italy, my father’s homeland. I hoped it would pull me out of my rut and be something to look forward to. Finally, I’d taste the glorious food, breathe the garlic-infused air, and walk the cobblestoned streets of my people! But one detail gave me pause: I lacked a travel buddy. For an anxious introvert who avoids spur-of-the-moment adventures with strangers, this presented a challenge I’d need to overcome.

At first, I felt sorry for myself. But once I reframed the trip as an opportunity for personal growth, I grew excited at the prospect.

At first, I felt sorry for myself. But once I reframed the trip as an opportunity for personal growth, I grew excited at the prospect. This meant I wouldn’t have to satisfy anyone else’s whims but my own. Nor would I have to abide by any unwanted spontaneity that might contribute to my anxiety. If I didn’t want to break the ice with others, I could just enjoy Italy on my own.

A hardcore planner, I spent the four months leading up to my solo, two-week trip brainstorming, budgeting, and booking. I chose to go in May, an ideal time to visit Italy because: 1) The heat wouldn’t have yet reached inferno levels, and 2) It would be less crowded than in the summer. By the time I took off, I was armed with a strategically-packed carry-on and a thoughtful itinerary, including downloaded Google maps of each stop of my journey so I could access them without WiFi.

After a red-eye flight, I landed in Venice with a plan: check into my Airbnb, freshen up, get gelato at a non-touristy spot I’d already researched, and then start a free walking tour. Everything went off without a hitch until I bungled the meeting spot and missed the tour entirely. For a first travel fail, it wasn’t a total day-ruiner, so I shook it off and pivoted in search of an afternoon snack instead. I had already researched the cheapest places to eat in Venice and chose a hole-in-the-wall wine bar called Bacareto da Lele known for its one-Euro paninis.

A legendary spot for Venetians, I waited patiently like a polite Canadian behind a queue of older local men. It took me way too long to realize they were not lined up to order, but instead were just chatting and smoking with the owner. It goes against my nature to elbow through a crowd, but I was forced to swallow my docility in the name of two small meat-and-cheese paninis.

One in each hand, I gleefully sat on the steps of the canal for my first Italian meal. Just as I was about to take a bite, a giant seagull came out of nowhere and plucked it from my hand. The beastly bird tossed the bread aside, beaked the salami and provolone, and flew away. When I noticed people around me laughing, I got over my initial shock and cracked up too. All my careful planning couldn't possibly account for spontaneous bird theft, so I had to roll with it and seek the silver lining: eating only one panini left room for a slice of pizza and another gelato. Tutto bene!

Through my solo Venetian wanderings, I indulged my introverted side. I genuinely enjoyed my own company while I people-watched in San Marcos Square and took myself on a lovely dinner date for one. I thought back to how intimidated I initially felt about travelling solo, but here I was proving that I could have a European adventure on my own. This early realization set the tone for the trip and I started to relax into the experience—even when my delayed train to Padova almost sent me into a panic. I was headed to Scrovegni Chapel and was going to be late!

As a (former) art history nerd who studied the Renaissance, the Giotto frescoes were the sole reason for my visit to Padova. Thankfully, my helpful guesthouse host called the chapel and confirmed I could use my ticket later in the day. Crisis averted! Still, that minor snafu sent my tummy into a tailspin. I guess not all travel anxiety can be averted.

Still, I continued on. After a short stay in beautiful, crowd-free Padova, I ventured to Bologna, known to locals as La Grassa, or “the fat one” because of its rich food. Between sips of Lambrusco—a delicious sparkling red wine served cold—I appreciated that I could experience Bologna's stunning views and luscious cuisine my way: at ease by myself without having to compromise with anyone else.

I thought back to how intimidated I initially felt about travelling solo, but here I was proving that I could have a European adventure on my own.

While touring the city’s vibrant street art and hiking through the world’s longest portico to Santuario di Madonna di San Luca, my days in Bologna aligned with the shy person I am: one who’d rather observe strangers than converse with them. Despite what narratives around travel often suggest, you don't have to be outgoing or spontaneous to enjoy escapes far from home.

The more I experienced this firsthand, the more I came to really believe it. I leaned into my shy girl travel style in Cinque Terre, a collection of five hillside villages overlooking the Ligurian Sea. On Italy’s rugged northern coast, I stayed in Riomaggiore and ate arancini on a rock during an idyllic sunset with views of the cove’s iconic cascade of brightly coloured houses. When the rocky outcrop flooded with selfie-stick tourists and couples on romantic picnics, I felt my first pang of loneliness. It was brief but potent—I wished to share the staggering magic of this place with someone I loved too. But as I read, listened to the ocean waves, and wrote in my travel journal, the loneliness turned to gratitude that I had the freedom—and confidence—to take this dream trip alone. Northern Italy was turning me into a self-assured traveller. I hiked more than 300 steps in Corniglia. I ate life-changing basil gelato and bruschetta, savouring the power of Italian cuisine in quiet, tranquil moments alone.

On a balmy night in Florence, I mingle with the bittersweet unease of loneliness once again. Though by this point, I’ve taken myself on enough dates around Italy to know how to embrace this feeling, leaning into the romance of solo travel even when it’s uncomfortable. I’ve made accommodations for my anxious side with careful preparation, a process which not only fuelled my enthusiasm, but also calmed my jitters, distilling my anxiety into a confident sense of you’ve-got-this. It equipped me to handle every minor mishap so far.

When that lonely pang hits, I remember that this trip has pushed me so far outside my comfort zone

Now, after walking all day in the intense heat, my feet are sore, I smell like a locker room, and I’m ready to crash at my hostel. When that lonely pang hits, I remember that this trip has pushed me so far outside my comfort zone, inspiring me to both defy and embrace my shy-girl tendencies. Here in Florence, I now know you can appreciate your own company, and also feel lonely while travelling solo—both can exist simultaneously.

Anyone who’s been to Florence knows how enchanting the birthplace of the Renaissance is once the sun sets. The Ponte Vecchio lights up the Arno River while street musicians serenade onlookers. I stop to listen to a woman in a ballgown play violin on the edge of a medieval fountain. As she plays “My Heart Will Go On,” a little boy next to me starts singing along. It’s a cinematic pinch-me moment. While I wish I could share it with someone, in the absence of a travel companion, I relax my resting poker face and allow my emotions to bubble up instead of pretending to be tougher than I am. When the tears come, I thank Florence, the violinist, and the singing child for breaking an emotional dam I didn’t know I had.

This article is part of the
Issue 5

Long Reads

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