Castiglion Fiorentino Travel Guide: Bread, History, and Tuscan Views
- Yaroslava Andrijauskas
- Aug 14
- 7 min read
Ah, welcome to the magical and historic Castiglion Fiorentino in Arezzo - its small enough to wander in an afternoon, yet big enough to surprise you at every turn. I came here without much of a plan, just a curiosity for what I might find. And what I found was a place where mornings smelled like fresh bread, church bells marked the passing hours, afternoons hummed with quiet streets, and evenings slipped into gold. This isn’t a “10 things you must do” list - it’s a slow walk through my own experience, with a few stops you might love too.
Beyond my recommendations in this travel guide, I wish for it to immerse you into Castiglion Fiorentino. Imagine as if you yourself is walking the streets and taking in the views. The photos from my trip will surely help. And beyond that this might help explore Castiglion Fiorentino on your own when, once you get a ticket through Trainline and take that train from Florence, or maybe you might rent a car and go on a roadtrip. Either way, I hope my recommendations will help you explore this wonderful, old, historic town.
What You’ll Find Along the Way
A quick list of the spots I visited and mentioned throughout this post. Each has a link imbedded so you don't have to search:
La Boutique del Pane – Cozy bakery with delicious handmade breads, pastries, pizzas, and maybe even pasta (if memory serves).
Bar 2000 – A relaxed spot for your morning coffee and pastry; also serves as a bar later in the day.
Il Buongustaio Trattoria Alimentari – Trattoria and grocer offering fresh bread, pastries, pantry essentials, and lunch.
Da Muzzicone – Local restaurant near the Church of San Francesco, great food. Try the Florentine steak!
Chiesa di San Francesco – 13th-century church with frescoes, tombs, and a peaceful cloister.
Piazza del Municipio / Logge del Vasari – Town square with stunning views of the valley and surrounding countryside.
Antico Caffè La Posta – Family-run café at the corner of the Loggia with excellent pastries and aperitifs.
L’Antico Forno di Magi Alberto – My favorite bakery in town, with fire-stove bread and early morning charm.
Museo Civico Archeologico – Learn about the Etruscan roots of the town and visit the underground archaeological path.
Cassero Tower & Rampart Viewpoint – An elevated viewpoint near the tower, offering one of the best panoramas of the valley.
Castello di Montecchio Vesponi – A striking historic castle in the nearby town of Montecchio; beautiful walk and scenery even if the castle is closed.
A Quick Tip on Arrival & Groceries
As you arrive in town, whether by train or car, and plan to stay more than a day, I recommend stopping at Gala Superstore, located just behind the train station. It’s a convenient place to pick up groceries and essentials before heading uphill into the old town.
A few things to keep in mind:
Taxis are limited in the area, so unless you have a rental car, expect to walk. The uphill walk to the main gate (Porta Fiorentino) takes about 15 minutes.
If you're driving, the streets inside the old town are one-way. If you miss your turn, you won’t be able to simply circle back - you’ll need to exit through another gate and re-enter through Porta Fiorentino. It’s not complicated, but good to know in advance.
Step into History at Porta Fiorentina
And here we are - Castiglion Fiorentino. Or as I call it - the town of peace, freshly baked breads, and breathtaking views.
Before you enter the town through the Porta Fiorentino, to the left of the it consider visiting:
- La Boutique del Pane - a delicious homemade baked breads, pastries, and pizzas (real pizzas, not american pizzas). I think they even sell pasta? But my memory is a little foggy on that.
- Bar 2000 - great for a morning americano, espresso, or cappuccino - whatever you fancy, and a yummy treat. It also doubles up as a bar. I came here on numerous mornings to grab myself a pastry and an americano.
Entering the old town through the main gates of Porta Fiorentino you are now standing in over 2,500 years of history. Let that sink in - 2500 YEARS. Can you imagine that it looked nothing like it does now?! Back in the 8th century BC it started as an Etruscan settlement. While the town you see today was built in medieval ages, between 12-17th centuries, and the modern buildings grew around it with time.
On the main street of Corso Italia stop at Il Buongustaio Trattoria Alimentari - there you can have a wonderful lunch or dinner - personally, I went there for the fresh breads, pastries, and a few pantry items to take to the rental I was staying in. Everything was always fresh. No one spoke english there, but my broken Spanish and google translate came in handy. 😌
As you keep walking up, take the second left after entering the main gates to come to the Square of San Fransisco where a restaurant Da Muzzicone (where I tried my first Florentine steak!) and Chiesa di San Francesco - the Church of San Fransisco is located. Dating back to the thirteenth century, I only got to wander the cloister and spent time admiring the frescoes and ancient tombs, but it was enough to keep me there for quiet some time admiring the art and history.
Go back out onto the main street and keep walking up to come onto Piazza del Municipio or the Town Hall Square where you will find Logge del Vassari with a spectacular view into the valley. I loved coming here in the mornings when it was quiet, and looking out, taking in that absolutely gorgeous view of the countryside with the green rolling hills, olive and grape groves, and countryside houses with terracotta roofs. If you've read my previous post about the mystical way I found myself in Castiglion Fiorentino, this is also where you will find the sculpture by Andrea Roggi. While in the left corner of the Loggia you will find Antico Caffe La Posta owned by a nice and fun family. I highly recommend all the homemade pastries or you can stop later in the day and enjoy an aperitif of a glass of wine with a view.
Go back onto the main street to continue along it, now it becomes Via S. Michele, and as you reach the end of the building on the right - you are officially at my favorite spot in town - L’antico forno di Magi Alberto. Referencing back again to my post about the mystical way I ended up in Castiglion Fiorentino - this is where I saw the owner on a few early mornings bringing the firewood in. The smells that would fill the streets in the morning (because I was living in the building right next to it) mmm - I cannot describe, you have to experience it. The freshly baked breads in the actual fire stove…it’s a one of a kind smell. Warning: it is open only in the mornings and they close early too, check the hours to be sure.
If you go back to Piazza del Municipio and face away from Vassari Loggia, so it’s behind you. You are facing two buildings: Comune di Castiglion Fiorentino and the Civic Archeological Museum (where you would want to go if you’d like to learn more about the Etruscan past of the town). Between them you will see a street going up the ramp - Via delle Carbonaie. As you start up the ramp to get onto Via delle Carbonaie on the street take a right to take a path up another ramp, through an archway and here you are - this is where you will find one of most amazing views of the valley from the top, as well as the Cassero Tower - which I know you can go up, but when I was there, unfortunately it was closed. From research, I know that there has been numerous excavations here, and there is an underground archeological path where you can see the past of the town - again, for that you will want to go to the Civic Archeological Museum. I’d say take it all in here…spend a little time wandering an ancient site and enjoy the views.
From here on out, get lost in the streets of Castiglion Fiorentino, they loop around and take you onto other streets. It was very intriguing to see how people live here. Their sturdy old wooden doors, colorful flowers in clay pots, I even stumbled upon some chickens in someone’s front yard, and a few stray cats laying around, taking a midday nap in the sun.
I don’t have all the recommendations for Castiglion Fiorentino. Though a small town it does have an amazing historical past. Besides wondering the streets and on occasion going down to the supermarket by the train station, I went hiking in the hills, did I know where I was going? Not exactly, but I marked off some pointers on the map app and set off. Part of the way did take me along the road without side walks, but it was pretty safe and I only saw a few cars. Stoppping so many times to look out and take in the views of the Tuscan hills. I wanted to just stay at every spot and not move.
On another day I also made it to Castello di Montecchio Vespone. Though it seems to be closed to the public and no hours are posted on Google or their website, but it was a beautiful walk and a great view. I also find it fascinating to be looking at historic sites, structures…it baffles me that someone built it hundreds, sometimes thousands of years ago. How many people lived there. How many saw it later throughout the years before me. And how many will see it after I’m gone. I don’t know about you, but it is such an amazing thought that seriously tickles my brain and brings me in awe.
And here you are, I do wish for you to enjoy your time in Castiglion Fiorentino. Wonder the streets, enjoy delicious food and wine, and the quiet moments while you’re looking out onto the rolling Tuscan hills dotted with the olive groves. And I wish for this travel guide to do just that.
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