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If you leave Arezzo and take the eastern side of the Valdichiana, you pass through Olmo, Puliciano and Rigutino before reaching CASTIGLION FIORENTINO. The origins of this town go back to the late Archaic and Hellenistic age, and are closely linked with its strategic importance in a hilltop position that surveys the vital communication route between Arezzo and southern Italy. There was a link between Arezzo and Castiglione as far back as the year 1000, and both the perimeter of walls which were enlarged in the 13th century and the transformation of the Cassero were due to Arezzo. Later on, it was dominated by Perugia and became known as Castiglione Aretino but, when it became part of the Florentine Republic after 1384, it took on the name it retains to this day. The centre of the town is Piazza del Municipio with the so-called 16th-century Logge del Vasari, opening so wonderfully on to the valley below. Opposite is the 16th-century Palazzo Comunale which was erected above a pre-existing building and which was itself remade during the first half of the 20th century.
The Cassero, or keep, was constructed between the 11th and 12th centuries, and later reinforced during the rule of Perugia with the construction of the Casseretto. Within the building is the Pinacoteca Comunale, or picture gallery, containing art works of great importance. You will see a late 13th-century wooden Crucifix, a San Francesco by Magarito d’Arezzo, a fragment of a Maestà, or Blessed Virgin Enthroned, by Taddeo Gaddi, and two works by one of the leading lights of Renaissance painting, Bartolomeo della Gatta, St Francis receiving the Stigmata made in 1486 and St Michael Archangel which, it seems, the artist painted with one of his pupils, Matteo Lappoli. The gallery also houses medieval masterpieces of the goldsmith’s art, such as the Reliquary Bust of St Ursula from the late 14th century, as well as other pictorial works by Giovanni di Paolo, Jacopo del Sallaio, Papacello and Giovan Domenico Ferretti.
From the Piazza del Municipio, you go down to the lower section of the town where you find three important churches, the Collegiata di San Giuliano, the Pieve Vecchia and the Chiesa del Gesù. The Collegiate Church, which was reconstructed between 1840 and 1853, has some valuable works, including a Madonna and Child Enthroned between Angels and Saints by Segna di Bonaventura, an Adoration by Lorenzo di Credi, and an admirable painting by Bartolomeo della Gatta of the Madonna and Child Enthroned with Saints from 1486. One of this artist’s assistants, Angelo di Lorentino, painted the Madonna and Child Enthroned between two Saints in the second decade of the 16th century. He was the son of the better-known Lorentino d’Andrea, a disciple of Piero della Francesca. The Pieve Vecchia, rebuilt in 1451, is important because it possesses a splendid fresco of the Deposition of Christ painted in 1483 by Luca Signorelli.
Before arriving at Cortona, the jewel of the Valdichiana, you come to the CASTELLO DI MONTECCHIO VESPONI which was a possession of the Guasconi family in the year 1000 but which, after the battle of Campaldino in 1289, came under the sway of Florence. It was awarded to the English soldier of fortune, John Hawkwood, known in Italy as Giovanni Acuto, and still retains a number of 13th-century elements.


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