Okay. I’m definitely not a virgin solo traveler, but until a couple of months ago, I was a virgin when it comes to traveling alone anywhere outside of the U.S.

 

Which, if you didn’t know, is like… the whole rest of the world.

 

In fact, it wasn’t until I found myself wandering down the nearly vacant arteries of Siena, Italy on that very first night, the echoes of my bootsteps ricocheting off of medieval, foreboding city walls, that it struck me how truly alone I was in a foreign place.

How did I get here?

Piazza del Campo at night.

I’d arrived in Siena after spending an amazing week in the southern part of Italy near Sorrento with my best friend Alaina and a group of women we met during our culinary tour with The International Kitchen. Basically it had amounted to 6 days of gluttonous feasting, wine consumption, cooking classes, more feasting, and even more wine consumption while getting chauffeured to the top sights around the peninsula — wine tasting on Mount Vesuvius, ceramic shopping on the Amalfi Coast, Michelin star dining in Sant’ Agata, clothes shopping in Sorrento — and our nights resting peacefully in a beautiful 4-star hotel with a view overlooking the Gulf of Naples and the sleeping Vesuvio.

It was rough.

But long before Alaina and I booked our airfare, I knew I would want more. Though not quite twice the size of the state of Florida, Italy is vast in its array of cultures, cuisines, terrains, and temperaments. If I was going to make the 18-hour trip abroad, I wanted to taste at least one other slice of it. And Tuscany, I’d decided — with its wide rolling vineyards, fortified hill towns, uniform rows of cypress trees, and streets down which Renaissance artists actually used to walk — was where I wanted to take a bite.

Stick-thin Cypress trees accent the landscape like happy little birthday candles. In the summer, Tuscany is also covered with bright yellow sunflower fields.

Alaina has two little kiddos, so I knew she’d be heading home and I’d be on my own after our culinary tour. The whole idea felt very Under the Tuscan Sun, only I don’t sustain myself on my writing, and my husband’s not an asshole. So, in an effort to avoid too much time wandering aimlessly by myself, not buying 17th Century villas or picking up sexy Italian men, I planned a fairly full itinerary.

 

 

My strategy was to pick two base towns — Siena and Florence — from which I could explore the surrounding area and experience several different lodging options. And since I really didn’t want to rent a car, I picked a couple of day tours — one culinary and one adventure — as a way to see the Tuscan countryside. Also, since I’m not super organized, I picked another tour to introduce me to the major sites of Florence (that way I wouldn’t have to figure them out myself), and another tour that would take me to dine at a farm in the hills of Tuscany.

Because why not?

Umm… it wasn’t as complicated as it looks.

The thing is, I’ve admired female solo travelers my entire adult life. I’ve romanticized their adventures and lived vicariously though their stories. Like a kid who thinks he wants to be an astronaut before learning about the vomit comet, it’s easy to think you want to be something before you fully understand that means.

So what was it like to travel solo?

Lonely.

 

I mean. It seems obvious in retrospect, but I think I thought I’d be better company.

 

On paper, I did everything right. My itinerary was extremely well-paced — a smattering of tours and time alone — and I never felt exceedingly rushed or exceedingly bored. At first I was worried that I’d signed up for one too many tours, but they actually turned out to be lifesavers when it came to the much-needed social interaction that feeds extroverts like myself.

I did a lot during that week. All of my favorite parts are highlighted in green.

Day 1: Took 3 different trains (including the amazingly high-speed Italian Frecciarossa) from a suburb of Naples to Siena.

My  business class car on the Frecciarossa.

Overspent on cab fare to get to the gorgeous Hotel Santa Caterina, where I checked in for 2 nights. From my room, I got my first real glimpse of why everyone loves Tuscany.

Explored Siena at night and experienced my first taste of dining alone in a foreign country. I loved the food, but I didn’t love staring at a wall.

Freaked out on my walk back to the hotel as I passed a gate that suspiciously appeared to be labeled “Psychiatric Hospital.”

Found out later that it was a psychiatric hospital, but it’s been annexed by the university.

Day 2: Day-long guided tour including wine tasting of the Tuscan countryside by MyTour.

Explored Siena at night. Again. Grabbed a slice of pizza and ate it sitting on the ground in the Piazza del Campo. Alone. Again. Wandered around on dark, medieval streets and realized exploring my new town exclusively by night probably wasn’t the best way to gain a first impression.

Day 3: Check in at Airbnb on the other side of Siena for 2 nights. My hosts, 2 sisters around my age, had a friend visiting from India. So while I’d been hoping to hang out with them a bit, I really didn’t see them at all. Instead, I walked around by myself. Again. At least this time, it was during the day. I listened to music.

I took pictures of my feet.

At dinner, I imposed myself on a lovely Canadian couple who were actually hiking from town to town through Tuscany. They took pity and sat with me until I finished eating.

Day 4: Day-long Vespa tour with MyTour.

Wandered down movie-esque Siena alleyways at night. Listened to Italian men singing loudly through open windows. PEOPLE THERE REALLY DO THAT, GUYS. Listened to the quiet clatter of dinner plates and laughter of families.

Resigned myself to eating alone, but wandered into an amazing little restaurant with three community tables and made friends with a Dutch and Dutch-American couple at dinner and consumed copious amounts of wine. The Dutch/French/American woman and I decided to become bffs. I emailed her when I got back to the apartment. She never wrote back.

Day 5: Became inexplicably lost while looking for the giant church in the center of town. Wandered around for two hours. Found church. Took more pictures of my feet. Met a really nice American student and had lunch together. Checked in at Hotel Aia Mattonata in the countryside for 1 night.

Day 6-8: Figured out how to take the bus to Florence, since the train employees were on strike. Drug suitcases across rickety cobblestones over a mile to my FlipKey apartment. Enjoyed an amazing dinner in the countryside and Florence by night tour with Walkabout Florence. Took more pictures of my feet.

Dined alone several times. Saw some of Florence’s top sights with Walks of Italy. Actually teared up when viewing David. Had dinner with a fun group of people a friend set me up with. Early on the last morning, I discovered that my number to the cab company didn’t work. Walked to the train station. Took a cab to the airport. Flew home.

Alone.

Alone.

Throughout the course of my week alone, I passed the time wondering how many strangers’ vacation photos I’d end up in and trying to look like I knew what I was doing and attempting to have an original thought. (An onerous task in the birthplace of the Renaissance.) I was frustrated and sad. It took me an entire week to figure out that I was trying too hard. That being alone didn’t have to be work. On that very last day, wandering the sunny streets of Florence, I gave up. I stopped worrying about whether my hair looked perfect or my white pants stayed clean, and I sat on my non-Italian pleather jacket and leaned against the wall of St Spirito Basilica soaking in the very last of the season’s warm Tuscan sunshine.

Looking around, I realized a void had formed around me, like a force field of electromagnetic impulses that read stay away! This girl’s erratic. She’s a lonely, frustrated tourist and we don’t know what she might do.

What I did do was kick off my shoes to take one last Italian picture of my bare, solo feet.

Yep. I placed my cute Italian brand TJ Maxx sandals to the side and stretched out my legs, wondering at first if baring my feet in Italy was somehow dangerously blasphemous — and not just in the short-distance-from-Milan-fashion kind of sense, but in the leaning-against-a-medieval-church-barefoot kind of sense — and I immediately neglected to care. It was far too exhausting.

So this is what it’s like to be lonely.

I sat and observed the happenings in the square. The little girl running around with her bouncing brown puppy; the toddler boy chasing pigeons on the ancient stone steps. Then I closed my eyes. For 10 minutes, maybe 20.

When I opened them, I saw. I was no longer alone. Next to me and all around, I was surrounded by people. Many had moved from the shaded steps in front of the church to my sunny perch along its walls, and while I’d sat there, eyes closed and finally embracing being alone, the people who’d moved in around me were quietly removing their shoes.

*****

The truth is, I didn’t love being alone. But this is something I needed to learn about myself. In the end, I actually managed to take a moment and enjoy it, and that, ironically, was when I finally attracted company. It was a challenge that took me out of my comfort zone. It forced me to solve problems. It validated my independence. It was a test that took me 32 years to take, and I don’t regret doing it. Most people never do. If I hadn’t, I’d always wonder if I could — just like the women I admire.

These are things we need to do sometimes, just to make sure we can.

After all, Freya Stark walked around Arabia all by herself, and I walked around Siena all by myself.

I took off my shoes.

I encouraged Italians to take off their shoes.

And then, when I finally relaxed, I learned what solo travel was really like besides lonely —

Ultimately, ecstatically, freeing.