Why Castiglion Fiorentino Is Tuscany’s Best Day-Trip From Florence

Hello my adventurous friend!

One of my favorite photos I took in Castiglion Fiorentino

Looking for quiet towns in Tuscany for a day trip or longer? I thought I’d stumbled upon one I'd never heard of - Castiglion Fiorentino - but something about it felt oddly familiar. Here’s how this escape from Florence became one of the most memorable parts of my journey.

Back when I was in Florence, at one point it got a little overwhelming (friends with anxiety, you'll understand). I needed a slower pace and a little more peaceful environment. As much as I love cities -  especially historic ones - the upbeat energy of hustle and bustle, the variety of things to do and see, the constant sense of movement, and more…I E.N.J.O.Y. it so much. Yet, there comes a time when it can get too chaotic and depleting. That’s when my body, soul, & mind need to slow down and recharge. And if you ever find yourself needing the same, taking even a day trip from Florence to Castiglion Fiorentino is one of the best ways to slow down while still experiencing Tuscany.

While researching, I actually (drum roll please 🥁) decided to explore yet another city (duh, I know 🤦🏼‍♀️) - Turin - because there was an amazing deal on a completely new Airbnb near the city center. Modern, clean, aesthetically pleasing, and, of course, the low price made it oh so appealing.

Clearly, I was ignoring all of my burnout signs in favor of curiosity. “Oh, more places to explore! Plus, I’ve never heard of this destination. It’s going to be a-a-amazing! Lots of new things to do and see.” I was already looking up museums, sights, and pictures. All while, all the alarms and SOS flares were going off in my head.

Exploring and getting lost in old medieval streets

At the same time I stumbled across a really neat apartment in a small medieval town in Tuscany. Located in what looked like a centuries-old building - nothing like I’d ever seen before. It was rustic, charming yet updated to make it more comfortable. An exposed stone wall, large arches separating the living room and bedroom space with, and barrel vaulted ceilings. From the terracotta floors in the kitchen to the patio with an olive tree, everything was simple, yet full of charm and detail. But, I couldn't decide between two completely different spaces and places. So, me being me, I decided to pick a place by playing “a game”…because, who am I kidding, I was indecisive. 

“A game” consisted of messaging the owner of the small town apartment to see if credit cards were accepted in this small, small town - my thinking was that if that's the case, then I’m going, & if not - Turin will be the winner. She did reply by the end of the day, however, be it by chance or not, I only saw the message the following afternoon. She was giving me a green light for the credit cards ✅.

On my way from Florence to Castiglion Fiorentino

Ahh, if only you lived in my head (and I don’t wish that upon anyone), you would understand - I still decided to go with Turin anyway. Imagine my disappointment when I went to book and two (just TWO!) nights were booked out of three-plus weeks that I was intending to stay, which skyrocketed the price, because it wasn’t new anymore (!!!🤬). Somewhat desperately, I reached out to the owner to see if she would bring the price back down for my long stay for the days that were available, but she wouldn’t budge. Well, that meant one thing...

“Off to a random small town I go.” All packed, with the ticket on my Trainline™ app and all of my luggage I set off to Castiglion Fiorentino.

The ride from Florence took only a little over an hour. What really helped was that the owner of the apartment had a friend who was very kind to pick me up from the station as there was no way to get a taxi. And when I say I was grateful - I was BEYOND grateful. She didn’t just take me to the supermarket by the train station and waited for me there while I got groceries (on her insistence as, she explained - there wouldn't be a chance to do that in town), but once I realized that I would have had to walk up some pretty steep hills with two suitcases and a backpack if she hadn’t picked me up…I don’t know what I would have done without her! She was a lifesaver! 

My terracotta patio (the olive tree would be on the left). I had my breakfast here a lot.

As I settled in, exploring this new and unknown place was more than my top priority. I spent every morning getting lost in the winding old, medieval streets admiring the historic architecture and the views. Wandering outside the old town walls - I would walk by the olive groves - this was my first time seeing real olive trees and there were so many of them everywhere! 🫒

On some mornings I would stop at a local cafe just outside of the town’s main entrance gate for an americano and a pastry. But the real treat was a bakery in the building next to my apartment - L’antico forno di Magi Alberto. It was tiny and opened in the early hours of the morning. The whole street would be filled with the smell of freshly baked breads. 🥖🥐 I also knew that the baker was using a wood-fired stove, not an electric one, as I was lucky enough to see him every so often bringing wood in on the days the bakery was closed, if I left for my morning walks early enough. I tell ya, it’s a different smell and a different taste. You absolutely have to try it!

Then one day, that first week there, as I was on one of my usual exploration walks, I decided to take a closer look at one of the piazzas (later learning its name - Piazza del Municipio) while looking for a cafe called Antico Caffe La Posta (highly recommend! Everything is homemade as well) to switch my americano routine.

Part of the Piazza del Municipio and the view from the Vasari Loggia

All of a sudden, my eye caught something familiar - a sculpture of a tree protruding from a globe with a magnificent backdrop of Vasari Loggia and the Tuscan countryside that stretched beyond. At first I didn’t understand why I was having this deja vu feeling. My mind was frantically trying to figure out the mystery in front of me.

Inspecting this bronze sculpture closer, I noticed very interesting details - the trunk of the tree was actually made of two people stretching their arms out that sprout into branches. You could say that this couple is in love. Right underneath the trunk was a small golden ball protruding from the globe. On the plaque was a name - Andrea Roggi - date and the name of the sculpture along with the website information. Unfortunately, I do not recall the name of the sculpture. But it made me think of peace, love, and growth. 🌍

All of a sudden I remembered, Of course! A few years back I was exploring travel blogs and saw this particular sculpture with this exact backdrop as one of must places to visit in

The sculpture!!!

Tuscany. Not just that, I also recall looking up the name of the town on the map, realizing it was a tiny town and thinking that I would probably never go there. Or if I do, it’ll be decades down the road. But that picture mesmerized me. I wanted to see it in real life. And here I was, a couple of years later! Looking at it with my own two eyes, right in front of me. If this wasn’t manifestation, I don’t know what is. 😉🌠

I was baffled for quite a few days after this and absolutely loved coming to this sculpture and Vasari Loggia almost every day. My final thoughts are this - if you are ever in Florence - plan a day trip from Florence to Castiglion Fiorentino. Enjoy exploring this town and the views. And to help you do just that, my next post is a short itinerary for it! I’ll tell you more about what I did while there and give my honest recommendations on what to do and see. Bon voyage!