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What Solo Travel Is Really Like.

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.


Biz explanation: Before going somewhere, travel writers typically secure something called a Familiarization Trip (“FAM trip”) arranged by local tourism boards, who then seduce and pamper said writers with some of the best lodging, cuisine, and tours the local area has to offer. But since I’m not exactly working for Condé Nast Traveler over here (at least not yet) and the success of tourism in Tuscany doesn’t really depend on my sterling recommendations (I mean, Michelangelo’s David kind of sells himself), I reached out to hotels, apartment rental companies, and tour companies individually to arrange my own custom FAM trip in order to fit my travel style and cover ground at a pace that wouldn’t stress me out.


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?



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.



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.


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I love both Siena and Florence, but I have not done it alone. I feel like I would enjoy doing it in Florence more than Siena, or I need to do another trip there with others to get more acclimated. The eating alone if the one hard part. Knowing myself, I typically eat on the go or bring back several items and do a picnic in my room. But ultimately I do enjoy the freedom, although I do not do it often!


Florence was definitely better alone than Siena — I planned way too much time in Siena, but that’s just the way it worked out with the hotel situation. While Siena was gorgeous, Florence was a breath of fresh air for someone traveling solo since there was so much more to do!

Colleen Brynn

For me, when I travel alone, it’s like the only time when it’s actually ok to feel lonely. I’ve felt just as lonely “at home” as I have on the road, only at home, it’s like I’m not supposed to feel this way. Buahhh :'(
Anyway, no pity party here, just stating the fact. I like being alone, and I like my own company. I particularly like this state when I’m traveling.
I totally get your post, though. Don’t get me wrong. Plus it’s beautifully written, and I love the idea of sitting out in the sun, not giving a shit, and just soaking it all in.


I think that’s what I was trying to come to grips with — what it felt like to actually be lonely for real, and that it was okay. I mean, I’m home alone all day, almost every day. And when Justin deploys, I’m very much alone. But often it would take at least a month to truly feel lonely in that situation because I was still at home… but something about being in a foreign country made the loneliness SO much more palpable. I think it’s a good feeling to have in order to grow. And to learn how to not give a shit. ;)


I wandered around Dublin alone. I am more of an introvert so my own company is a delightful guest – maybe pathetically so lol. But I did find it lonesome during dinners. I felt the need to have my phone, a book and a notebook nearby so that I could preoccupy myself instead of listening in to other people’s conversations.

It’s funny, I also heard an Italian man singing into the streets in the middle of the night in Verona when I was there. It was very lovely.


YES! I loved hearing the Italian men sing though the windows. It was my favorite part of night wandering. But it also made it lonelier, somehow… hearing all of the happiness going on inside the apartments.

I don’t think feeling comfortable in your own company is pathetic AT ALL. It’s admirable, and something I’d like to get better at, which is why this was a really great challenge for me. :)


loved reading this post! i used to admire other solo travelers too.. and a lot of my friends do it really well. they make new friends instantly everywhere they go.. and they never seem alone because of it. i, on the other hand, am extremely introverted and don’t have the skills to do that haha i feel like i always feel very alone when i travel by myself and i’m glad that jacob is good company to travel with… though who minds the company of other sexy italian men! hahaha i wish i was there to hear them singing. i don’t think i’ve ever come across that on either of my trips to italy. i’m going to have to check out the area of tuscany next time! :)


That’s so funny! And I was thinking introverts had it easier when it comes to solo travel because they don’t NEED the company, but you’re right — it’s definitely easier for extroverts to meet random people. Which I definitely did! You for sure should check out Siena and Florence — and definitely bring Jacob because it’s such a romantic area of the country. Walk around at night — especially though the back alleyways of Siena — and you’ll for sure hear an Italian serenade. :)

Christina @

I have travelled alone, but never for long periods of time and what always gets me is when I see a beautiful view or something that’s just no fun to not be able to share with someone else :( Good for you for going it alone, as I know many others wouldn’t even try. Great post!


You’re SO right! My only consolation was knowing I’d get to share it with all of you, via photos, but it’s just not the same as someone being there.


Katie…..loved this post….but sorry you felt so lonely. I love to travel alone and the first trip I made to Italy I stayed for 6 months and did it alone. I think for me one of the reasons I love to travel alone is that I feel so free. Free to sleep late. Free to go to the beach all day and skip the museum. Free to drink wine all day. Free, free, free. Not obliged to ANYONE! I kind of spent a life of trying to make people happy and the feeling of just making myself feel happy without feeling guilty about it or trying to do what everyone else wants to do?? – – HEAVEN! And as you mentioned – – sexy Italian men didn’t hurt the situation either. After all…I MARRIED one of the sexy Italian men I met on that trip.

But in the end, I see that for you too, you felt free. It is a lovely feeling isn’t it???

I do have to say that I rarely ate dinner alone. Breakfast and lunch – no prob. But dinner alone was and is not for me. Not sure why.

Anyway…your shoe thoughts made me laugh a lot. You got it right……going barefoot ANYWHERE (even in your own home) is a big no-no for Italians. Ha, ha, ha…you should see my mailman when I come running down the stairs of the apartment with no shoes on to get my mail. That guy is ALWAYS staring at my feet. And I can actually hear his thoughts screaming: ” Putta soma shoesa ona your feeta!”

Ok…enough about the mailman and my bare feet. Your post and photos as always were fab! Buona domenica!!!


No need to apologize! It’s definitely something I needed to experience. I think it’s probably easier to travel solo when you’re single — you’re more inclined to stay in different types of lodging, go to different types of establishments, and talk to different types of people (aka. “sexy Italian men”) because you don’t have to worry about giving the wrong impression. When you’re young and available, the possibilities for romance and friendship are endless! And yes. Dinners were the worst. I came to dread that time of the evening — that one night where I ended up eating with the other two couples was SO much fun!

The thing is, at home, I always feel free. I mean, I’m definitely considerate of my husband and what he wants to do, but since we don’t have kids, we can be pretty selfish with our time. But what was really amazing at the end was the freedom from caring what other people thought! I was always worried that people would think I was weird for being alone. Or, when I travel with people, I worry they’re judging me for how I dress or what I say… it took me to the end of the trip to realize how liberated I was from that because I was alone! I was never going to see any of those people again. I hope I didn’t disrespect the culture too much though with my bare feet — I wouldn’t want to do that. Ha!

Your mailman judging your bare feet cracks me up. And can you believe others took off their shoes after I did?? Maybe they weren’t Italians but other tourists — either way, I think I started a movement. ;)


It’s good to know these things about yourself. Probably the longest I’ve really traveled alone was that trip when I saw you – ten days, I think? But I think my real comfort zone is more like four days. It is lonely traveling alone. And for me, creepy. I’m always afraid to do anything at night. Also, it sucks to not be able to say, “Look!” to someone and share a moment. On the other hand, you don’t have to compromise about anything, and that’s pretty cool. As for the eating alone thing, I either bring a book, or make sure I sit at the bar so I can chat with the bartender.


That was a long alone trip for you! On the plus-side, you stuck to an english-speaking country so it was possible to chat with bartenders. In Italy, even if I had actually seen a bar with a bartender like in North America, I couldn’t say much more than “good wine” or “how are you?” Ha! But even without the language barrier, it’s still lonely — and definitely easy to miss sharing those cool sights or special moments with someone. (By the way, I’ve missed you! Hope all is well with you and your beautiful family!)


Yes….great point…for sure being single is going to change the dynamic in all regards (not just in the men department). I still make solo trips on occasion, but usually only for 3 days and only about once every 2 years. And now you have me thinking about how different I am when I take these trips relative to that first trip to Italy. VERY INTERESTING! You are SUCH a psychologist! :)

And no…..there it is not disrespectful to take off your shoes….Italians just don’t get it. My mother-in-law asks me EVERY time I go to her house if I need to borrow some slippers. Anyway, I cannot believe others took off their shoes too. Yes…for sure a movement…or maybe even a revolution! BRAVISSSIMA!


HA! See?? The short solo trips are definitely good for you, but just not the same when you’re not on the prowl. ;) The shoe thing is SO funny. Now that I think about it, my dad is married to a Chinese woman, and she insists we wear “house shoes.” We cannot wear our outside shoes into the house under any circumstances, but we can’t go barefoot, ether. We’re supposed to bring “house shoes,” or slippers. Maybe it’s just us westerners who like weird, naked feet! :)

A Lust Letter To Siena. - Domestiphobia

[…] emotion — the awe of wonder at discovering the beauty that lies in your hidden nooks; the depth of sadness at walking your cold streets alone — then the memory of our intimacy, no doubt, won’t soon fade from my […]


How the crap did I fall off your mailing list??! I’ve missed reading your stuff! Beautiful, smart, poignant, feisty, weird, and all the gratuitous foot porn I can handle. Keep it comin’! :) <3


Aww, I’m guessing it has something to do with being an insanely busy college student. But now that you’re going to be an insanely busy professional occupational therapist, you should have *plenty* of time to dick around on the internet. ;)


I appreciated your honesty! I have done a few solo trips and although I enjoy them eating alone in a restaurant or the time I was on a private tour w 3 other couples was tough. It does teach you so much about yourself including strength and independence! I love Italy too! I went to Florence a few years ago and the trains were also on strike then! Lol. I was in Naples and Sorrento in September. Jealous of your trip experience there!


I appreciated your honesty! I have done a few solo trips and although I enjoy them eating alone in a restaurant or the time I was on a private tour w 3 other couples was tough. It does teach you so much about yourself including strength and independence! I love Italy too! I went to Florence a few years ago and the trains were also on strike then! Lol. I was in Naples and Sorrento in September. Jealous of your trip experience there!

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