Castiglion Fiorentino is a town of 13,000 people (2017) in the Italian province of Arezzo. It lies at the centre of a triangle formed by important cities such as Florence, Siena and Perugia. Castiglion Fiorentino was founded as an Etruscan settlement and became a medieval village. It lies close to the famous Valdichiana and Cortona.

view

Get around

Can be walked on foot.

street

See

The tower of the ancient castle (Torre del Cassero) dominates the town. This charismatic town has much to offer any visitor including its beautiful medieval walls, beautiful churches, art treasures and numerous Renaissance structures, e.g., the Loggia by Vasari at the Piazza del Comune.

Castiglion Fiorentino also has many festivals throughout the year including the famous "Palio dei Rioni", a horse race among the three ancient Rioni (boroughs) of the town (Porta Fiorentina, orange-green; Cassero, white-blue; Porta Romana, red-yellow) in Piazza Garibaldi, the largest square of the town, held on the 3rd Sunday of June, similar to the Palio of Siena. It includes a colourful and energetic display of the ancient custom of flag-waving dating back to the 13th century (in the weekend preceding the horse race, a spectacular contest between the three groups of flag-wavers is also held). All these are extraordinary shows not to be missed.

A splendid loggia by Vasari looks out onto the beautiful Valle di Chio - or Valle di Dio according to one of the Medici dukes after taking the town for Florence.

Eat

• 1 La Pampa Ristorante, via Dante 23, Old Town, ☏ +39 0575 659 004. Closed M Tu. This restaurant serves steaks and wine imported from Argentina, pasta and vegetables. Save room for the dessert of imported dulce de leche. The owner is a young Italian and his wife. Steak samples are presented raw on a wooden plate before you order. Outdoor seating in summer with a view over the village. €35. 
• Ristorante Da Muzzicone. Fiorentina/Chianina steak. Be careful, the owner believes foreigners are prey to rip-off. The steak nonetheless is unmissable. 
• Coco Palm, the local gelateria is a must.

Drink

• Regiro Pub. Nice place, more sophisticated than Velvet Underground. The hosts are really nice. 
• Velvet Underground. Live music concerts; a bit more grungy and the owners only care about your money, but the people there are less pretentious and can be a lot of fun 

Sleep

• 1 Villa Senaia (country house), Loc.Noceta, 58/a, ☏ +39 3334001234, info@villasenaia.com. Check-in: 16:00, check-out: 09:30. Ancient stone farmhouse, located in a strategic position, with various paintings of flowers hang on the walls. The living room is plain and simple, with stone walls where the fireplace stands, and satellite TV. The kitchen will give you access to the patio area with facilities for dining out in front of the swimming pool and a view of the entire valley.On the ground floor you can also find a bedroom and another one with shower. An external staircase leads to the balcony, two double rooms with shared bathroom and a bedroom with private bathroom and access to the loggia. The villa has a private garden surrounded by flowers and trees, an outdoor oven and barbecue, a laundry room and private parking. The owners, who live nearby, will welcome guests on arrival with a small buffet lunch. If you wish more privacy, the owners will not interfere with the guests' stay. Cultural cities such as Cortona, Arezzo, Montepulciano, Siena, Florence can be reached in less than an hour. (updated Nov 2015)

Go next

• Arezzo
• Cortona
• Florence
• Perugia
• Siena
• Valdichiana