Castiglion Fiorentino, under Cortona’s sun

Castiglion Fiorentino

Located on the top of a hill in the province of Arezzo is the small walled town of Castiglion Fiorentino. Surrounded by beautiful olive groves, the town enjoys magnificent views over the Val di Chio, the Valdichiana and the pre-Apennines. Castiglion Fiorentino lies at the centre of a triangle formed by the cities of Florence, Siena and Perugia and is a perfect base for exploring the surroundings.

02 The Cassero's tower

The town walls and overall architecture are late medieval, however remains of an Etruscan city wall belonging to the 4th century B.C. has been found underneath today’s Piazzale del Cassero as well as the vestiges of a 12th-century Etruscan temple under the church of Sant’Angelo. The main entrance to the town’s historic centre is via Porta Fiorentina, erected during the 13th century and later enlarged by the Perugians to connect the castle to the outside walls. The town’s fortress, the Cassero, was completed in 1367. Used as a convent during the 15th century by the nuns of San Girolamo, in the 19th century much of the stronghold was destroyed and the remains used as a prison.

03 Vasari's loggia

A better fate has been reserved to the above-mentioned church of Sant’Angelo. Built in Romanesque style between 1229 and 1239, the church, during the centuries, has served as hospital, wine cellar, workshop and today, totally renovated, as the town’s official museum and art gallery. Down in the town hall’s square, Piazza del Comune, is the superb nine arch loggia Vasari constructed in 1513 and from which visitors enjoy a view over the valley.

04 Flag wavers

Castiglion Fiorentino organizes many events during the year. The week leading up to Easter Sunday, the town parades along the streets re-enacting a scene from the Passion. This has been done for the past 400 years. The month of May is devoted to enhance the area’s local products and culture: trade fairs, exhibitions, concerts, sporting events, festivals and cultural events are held. The month ends with a meeting of vintage Fiat 500s and a medieval banquet, the Festa Medievale Biancazzurra. On the third Sunday of June the Palio dei Rioni is run: similar to Siena’s Palio, this horse race is held in Piazza Garibaldi and includes a very colourful and energetic display of flag-waving whose tradition dates back to the 13th century. Summer is full of fun fêtes in town and in the various surrounding hamlets: Pizza Festival in La Nave, Ostrich Festival in Manciano, the Archbishop’s fête, the Frog Festival in Brolio and the Grilled Steak at Montecchio Vesponi. In October Castiglion Fiorentino celebrates the Days of Bacchus: two weekends full of wine and delicious local products. At the end of November it’s time to taste the new olive oil and a festival, Oliomangiando, is held on the last weekend.

05 Accommodation in Castiglion Fiorentino S170

Therefore any period of the year is perfect to visit Castiglion Fiorentino: be it spring surrounded by bright red poppies, or summer with its dazzling yellow sunflowers, all year round travellers will be welcomed by the typical Tuscan cypresses and by the silvery olive trees. If you do come and visit we recommend this magnificent villa with swimming pool and a breathtaking view over the two valleys. Perfect for a group of 8, this villa will allow you to enjoy Castiglion Fiorentino and its beautiful surroundings at the most.

06 Accommodation in Castiglion Fiorentino S170

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