Castiglion Fiorentino is an ideal village to explore on foot.
Here is a 10-stop itinerary to discover its beauties and fully enjoy the life and rhythms of this fascinating and characteristic town:

1. Porta Fiorentina: Start your tour at this historic city gate, built in the 15th century, which serves as a perfect starting point for your visit. Once you pass through the gate, you will find yourself on the main street where we recommend stopping for an aperitif or a coffee in the many charming local establishments.

2. Piazza del Municipio and Palazzo Comunale: Continue towards the heart of the town, where you will find the Palazzo Comunale, a 13th-century building with a facade decorated with coats of arms and inscriptions. The square is a great place to start getting oriented in the village.

3. Logge del Vasari: A few steps from Piazza del Municipio are the Logge del Vasari, an elegant Renaissance portico designed by the famous architect Giorgio Vasari. The loggia offers a fantastic view of the green Val di Chio below. You must take photos here; it is an unmissable panoramic spot!

4. Church of San Francesco: Continue to the Church of San Francesco, one of the most important churches in Castiglion Fiorentino, dating back to the 13th century, with frescoes and artworks of great historical value by authors such as Francesco Morandini, known as "il Poppi", Giorgio Vasari, and Salvi Castellucci. The church, overlooking the square of the same name, was built by the Franciscans in the mid-13th century on a pre-existing 12th-century structure and features a Romanesque-Gothic facade in sandstone with a slender bifora topped by a small rose window.

5. Torre del Cassero: Next, climb to the Torre del Cassero, a medieval tower that offers a spectacular panoramic view of both Val di Chio and Valdichiana. The tower still retains its original features and the charm of a medieval defensive structure. Its unmistakable profile makes it the main landmark and the true symbol of Castiglion Fiorentino. The climb might be challenging, but the view is worth the effort, trust us!

"The Cassero Tower (Torre del Cassero)"

6. Archaeological Museum: Located in the former convent of Sant'Angelo al Cassero, the museum displays Etruscan and Roman artifacts found in the area, offering a window into the ancient history of the territory and narrating the past of Castiglion Fiorentino.

7. Municipal Art Gallery: From Piazza del Municipio, continue uphill to the left to reach the Municipal Art Gallery. Don't miss this art gallery, which houses a collection of religious artworks, including paintings, sculptures, and relics from the medieval to the Renaissance period.

8. Church of San Filippo: Then head to this Baroque church built in 1717, known for its 18th-century wooden Crucifix dominating the back wall. The church was restored in 1874 and after World War II due to extensive damage from bombing.

9. Palazzo Pretorio: This historic building, located in the central square, was built in 1412 on ancient structures already modified in medieval times. It was the seat of the podestà and today houses the Municipal Library and the Historical Archive.

10. Walk along the Medieval Walls: Conclude your tour with a walk along the ancient walls that surround the village. These walls offer breathtaking views of the surrounding countryside and provide a perfect moment to relax while strolling in the open countryside under the shade of this enchanting and lived-in village.

This walking itinerary will allow you to immerse yourself in the history, culture, and beauty of Castiglion Fiorentino, making your visit unforgettable.

Photos Toscana.info /Discoverarezzo.com