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An Unexpected Issue When Traveling Solo in Tuscany

a woman walking down a sidewalk with a boat in the water

A sense of paranoia was not what I expected to feel on my first trip to Tuscany.

During most of my visit I felt like I was getting weird looks when I would buy tickets, go in to restaurants, or even stroll around the picturesque downtowns.

Was I unaware of a wardrobe malfunction? Are tourists not supposed to be here? Is this all in my head?

There was one instance that made it clear it wasn’t me being oversensitive.

I was visiting Siena and walked into a small restaurant on a busy square that was completely empty. It was just me and the two employees. The waiter looked at me and then almost frantically behind me with growing surprise.


I nodded and he (I’m not exaggerating) looked panic-stricken as he glanced at the 10 empty tables set for 2 people, as if wondering where to sit this freak.

I found it pretty humorous, but by the end of the day it was old when even buying a single ticket for the cathedral generated surprise. The next morning I was telling my bed & breakfast hostess about it, remembering how the first morning at breakfast everyone had praised my courage and confidence in coming there alone.

She confirmed it wasn’t just in my head. That area of Tuscany doesn’t get many solo travelers and those that are tend to be older men or college students. So while I was completely safe, I was definitely standing out as unusual. Apparently I needed to be 10 years younger or 30 years older to not stick out.

We joked that next time a restaurant expressed surprise about a table for one, I should burst into tears and tell them my boyfriend and I had just had a big fight.

If you go to Tuscany alone you will definitely enjoy it, how could you not!?, but more so if you know in advance that solo travelers are not the norm and you might get some surprise or funny looks.

And if that kind of thing gets to you, here are some tips on lessening the feeling of isolation

  • Stay in town vs the countryside. I stayed in the country and once I wrapped up my site-seeing around 4 or 5, I was too tired to get back in the car for an uncomfortable dinner at 8. But if it was just a matter of walking a block or two I would have poppd in somewhere for dinner and/or a walk around the town.
  • Stay in a B&B to make friends – You can also do this at a hostel, but now in my 30s my hostel days are over. A B&B is the next best thing. Your hosts are good sources of information, even camraderie and I found all my fellow guests very friendly and welcoming.
  • Take Group Tours – I strongly prefer to do my own thing on my own schedule, but if you’re not a fan of driving or taking public transportation solo, tours are a good way to see the sites and feel like part of a group.

More from this trip:

Iberia Business Class JFK-MAD
Iberia Lounge Madrid
Iberia Business Class MAD-FLR
An Afternoon in Florence
Wine Tasting in Florence: Best Wine Bar Ever

Full Disclosure: I may receive affiliate credit from links in this post or on this site which will help fund my travels. Thank you for your support!

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  1. Very interesting. I am here in Pienza, after leaving Florence for my first night, stopping in Siena for lunch on day 2.
    I am at a farm stay outside Pienza, it’s beautiful. So far I am doing ok. I am here for a month. I want to do a wine and cooking class and join some tours. Will post how things go from her. Yes, I rented a car and I believe the only way to see Tuscany.

  2. I’m about to head over to Florence. I’ll be traveling solo. I really want to eat good food, drink wine, see the beautiful country and just unwind. Based on your experience would I be better served staying in Florence and taking day trips or splitting my time between say Florence and Siena?

    1. I would split the time! Siena is beautiful and makes day trips to locations further south much easier. And you will be totally fine going solo as long as you’re aware in advance there might be awkwardness. 🙂 Hope you have a fantastic trip!!

  3. i am planning on doing my first solo to Italy (have travel to Milan and Venice before for work). Please suggest an itinierary, i have 14 days and would liek to see most of Tuscany. Starting and ending in Milan and Rome for flights. Thanks..

  4. Good evening!
    I’m heading to Italy on August 31 for 11 days.
    I’ll be solo for a couple of days and I’m thinking about taking a cooking and wine tasting class in Tuscany. Any ideas?

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