History and Territory


Castiglion Fiorentino is located on the top of a hill (m. 345 a.s.l.) from which it is possible to enjoy the silvery view of the pre-Apennines covered in beautiful olive trees of the Val di Chio and Val di Chiana. The historic center dominated by the Cassero Tower is surrounded by 13th-century walls, it retains its medieval layout and is built on the ruins of earlier Etruscan buildings (6th-4th centuries B.C.), as recent excavation campaigns have shown. Situated on the border between Tuscany and Umbria, it enjoys an ideal location from which it is possible to reach the major cities of central Italy (Florence, Perugia, Siena, Rome). During the Middle Ages, in the 12th-13th centuries, it became a municipality, and then, in the 14th century the town passed under various dominions (Florence, Arezzo, Perugia), until 1384 when it finally became Castiglion Fiorentino. In the mid-1700s great importance was held by the Grand Dukes of Lorraine as the implementers of the land reclamation campaign of both the municipal territory and the entire Val di Chiana.

Museums and Churches

The area of greatest historical and artistic value is without a doubt the Cassero area, located in the highest part of the town. Here you can visit the Archaeological Museum and the Underground Route. Inside the museum, the reconstruction of a portion of the roof of the Etruscan Sanctuary (found in the Piazzale del Cassero) stands out among notable artifacts; there are also small bronzes from 560 and 550 B.C. found during excavations in the nearby hamlet of Brolio.

In addition to the medieval remains, the Underground Route presents evidence of the first Etruscan settlement from the eighth century BC.

In the same area of the Cassero there are the Church of St. Angelo and the nearby Art Gallery. The Church is home to the beautiful 13th-century wooden crucifix by an unknown author, formerly attributed to Cimabue. Passing through the tiny door that connects its hall to the Pinacoteca, we are met with works of medieval jewelry of French manufacture such as the bust of St. Ursula (14th cent.) and the valuable reliquary of the Holy Cross (13th cent.). And there is no shortage of pictorial works, such as a depiction of St. Francis by Margarito d’Arezzo from the 13th century, a fragment of a Majesty by Taddeo Gaddi (Giotto’s pupil) from around 1328, two panels St. Michael the Archangel from around 1480 and the Stigmata of St. Francis from1486 by Bartolomeo della Gatta.

Descending from the Cassero area toward Piazza del Comune, we encounter the beautiful Renaissance Loggia dating from 1513, later retouched by Giorgio Vasari ( the aftermath of this fact took the name Vasariano), which offers us a special view of the Valle di Chio.

Another important cultural venue, which is part of the Castiglionese Museum system, is the Pieve di San Giuliano Museum. There are numerous paintings and panels covering the 15th to 18th centuries; among them is the fresco Lamentation over the Dead Christ attributed to Luca Signorelli, next to which is a polychrome glazed terracotta, the Baptism of Christ, attributed to Andrea della Robbia. Inside the showcases are preserved numerous objects of gold jewelry, reliquaries and garments for the celebration of religious rites from various periods; among these the most valuable is the Tonacella di Petreto, whose manufacture is reminiscent of the production of the most illustrious Florentine workshops of the second half of the 15th century. There are also numerous wooden sculptures: dating from the 13th to the 18th century, some of them are still carried in procession today during “Settimana Santa” (Holy Week).

The Museum Square is faced by the Collegiata of San Giuliano and the Church of Jesus. The former, in the Neoclassical Style, preserves numerous works of art, including the Madonna Enthroned by Segna da Bonaventura from the 13th century, the Virgin Enthroned and Saints by Bartolomeo della Gatta (from 1486), the Adoration of the Child by Lorenzo di Credi (a pupil along with Leonardo da Vinci in the Bottega del Verrocchio), a polychrome terracotta depicting St. Anthony and an Annunciation both from the Robbiana School.

The Church of Jesus was built in the 16th century, and the interior features decorations from the late 1500s to the 1700s; of special interest are the coffered ceiling with biblical symbols of the Passion of Jesus from the early 1600s and the altar leaning against the back wall, the work of Filippo Berrettini, nephew of Pietro da Cortona. Inside the altar is a valuable wooden crucifix attributed to the school of Baccio da Montelupo from the early 1500s. Two valuable canvases are kept at the side altars; on the left is the Ultima Cena (1586) by Francesco Morandini, known as Poppi, a pupil of Giorgio Vasari; on the right is the Resurrection (1599) by Francesco Vanni.

The historic center also features the Church of St. Francis, with a Romanesque-Gothic sandstone facade; its interior, typical of churches of the Mendicant Order, has a single nave. The altars house notable works such as Vasari’s Madonna and Child with Saints (1548); Poppi’s Crucifixion; and Salvi Castelluci’s Vocation of St. Matthew. Of particular interest is the bronze-plated wooden crucifix on the high altar, designed by Gianbologna. Next to the church is the Cloister, whose current appearance dates back to the early 17th century in Tuscanic style and which houses frescoed lunettes.

Outside the city walls draws attention the monumental Consolation Church from the second half of the 16th century.

With an octagonal central plan, its interior contains a very fine stone altar by Filippo Berrettini that contains a small fresco, a Maestà, attributed to the school of Luca Signorelli and the Shrine of the Madonna delle Grazie del Rivaio.

A few kilometers away from the old town is the Sanctuary of the Madonna del Bagno and the 11th-century romanesque Pieve di Retina (Capuchins).

La Valle di Chio

On the west, the valley is bounded by the peaks rising to the east of the Valdichiana, particularly Mount Castiglion Maggio; to the east a ridge separates it, across the Montanina Pass, from the valley of the Nestore stream, a tributary of the Tiber. To the south it is enclosed by mountains culminating in the summit of the Alta di Sant’Egidio. At the entrance to the valley rise the town of Castiglion Fiorentino and the castle of Montecchio Vesponi.

The hills that form the ridge of the Val di Chio describe a portion of an ellipse that begins at Castiglion Fiorentino, passes through Mammi and Mount Castiglion Maggio, and continues to the Foce Pass, through which one reaches Palazzo del Pero and San Sepolcro. It then continues, touching on many places: the village of Caldesi, Mount Corneta, the houses of Renzana, the Fontanina and Montanina hillocks, the Montanina Rock, the hill of the Forks, Valcella House, the mouth of Ristonchia, and Mount Castel d’Ernia. It eventually ends near the village of Santa Lucia. The territory enclosed by this ellipse is almost entirely within the municipality of Castiglioni, with the exception of the village of Caldesi, Mount Corneta and the houses of Renzana, which belong to the municipality of Arezzo. There are a number of small towns in the Chio Valley whose origins date back to the medieval period. Some of these had a defensive purpose, as evidenced by the ruins of Mammi Castle, Tuori Castle, Castel d’Ernia and Montanina Castle. Others originated from “ancient villas” (Santa Lucia, Collesecco and Pergognano) that in the medieval period maintained an agricultural function. Still others such as Polvano, Santo Stefano, and Pieve di Chio were born from previous “spedali” that had the function of shelter and refreshment for travelers: one of the main communication routes between Tuscany and the Adriatic Sea passed right through the valley.

The area has always been very rich in water springs, which led to the development of the “water” cult (as a symbol of the fertility of the earth) especially popular in the early Christian and early Medieval periods (6th-9th centuries). In the Medieval period the cult was replaced by the more “Catholic” cult of the “Madonna del Latte”: there are numerous representations of the nursing Madonna; we find some in the frescoes of the sacristy of St. Francis, in the Church of St. Augustine, in the urban center and in the depictions of numerous tabernacles in Taragnano, Collesecco and Poggiolo.

The presence of waterways over the centuries led to the frequent construction of mills (“mulino” in italian), evidence of which still remains in the toponymy of some places such as Mulin Nuovo, Mulino Bianco, and Mulino dello Zoppo. The memory of the mills is so heartfelt that the pedestrian “Old Mills Trail” was recently created.

The entrance to the valley is the already mentioned Pieve di Retina, which was built in Romanesque times on the remains of ancient Roman baths and a sacred High Medieval building. During the Renaissance, the interior was rebuilt and the portico was redone according to the canons and taste of the time; the facade and apse still keep the Romanesque imprint.