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Leaving behind the city of Arezzo, and travelling along the eastern side of the valley, you come to CIVITELLA IN VALDICHIANA, a village which had once been a Lombard stronghold before it eventually became a feudal domain of the Bishops of Arezzo after the year 1000. Its moment of greatest development was in the second decade of the 14th century after which, in 1345, it became part of the domain of the Florentine Republic. Linking the present day with the past is the Porta Senese, the ruins of the 13th-century Castle and the Palazzo del Podestà which shows some 15th-century reconstruction work.
Inside the walls, there is also the Chiesa di Santa Maria which, although it dates from the 11th century, has been reconstructed many times. Inside, the Crucifixion and Saints was painted in 1602 by the Arezzo artist Teofilo Torri, pupil of Giorgio Vasari. On the outskirts of the village, there is the Oratorio della Madonna di Mercatale, a simple but picturesque building, constructed by the citizens of Civitella around 1630 in gratitude to the Blessed Virgin for escaping the plague.
The road now takes you to Gargonza. In the early 13th century, this village was a possession of the Ubertini family and, in 1302, during their dominion, tradition relates that there was a gathering here of Ghilbellines and a number of Guelphic bandits from Florence, in which Dante also took part. In 1381, the Ubertini sold Gargonza to Siena from which it was ceded to the Florentine Republic in 1384. Acquired by the Loteringhi della Stufa family in 1546, the village was then sold, in the 18th century, to the Marquises Corsi from whom it passed through inheritance to the Guicciardini family who are still today the proprietors. Of its fortifications, Gargonza retains the tower and the remains of the ancient walls with their 13th-century gate. The Chiesa dei Santi Tiburzio e Susanna is also a medieval foundation, dating from the 12th century. On its portal there is terracotta Madonna and Child with Angels from the Rossellini circle and, inside, a fresco with the Madonna between St Anthony Abbot and St Bernard, dated 1483.
Going back now along the strada statale, you will come to the Santuario della Madonna delle Vertighe who is the patron saint of the Autostrada del Sole. The origin of the shrine lies in a Marian miracle when a small chapel was carried from Asciano by angels in flight and gently set down here, towards the year 1100. In the 16th century, the sanctuary was built around what had become a shrine, and it was restored in 1943. The façade is simple, with two downward inclinations and a portico on hexagonal pillars. The bell tower is a medieval tower topped with a Renaissance crown ascribed to Andrea Sansovino. Inside, the columns which separate the nave from the two aisles are surmounted by Ionic capitals, and the church possesses valuable works of art. In the left-hand aisle, you can see the Nativity of the Blessed Virgin, signed and dated 1627 by the Arezzo painter Bernardino Santini, and the diptych portraying St Savinus and St Romuald is by Ridolfo del Ghirlandaio, from 1520. In the apse there is a very precious wooden triptych which depicts the Madonna delle Vertighe and four Marian Stories in the central panel and, in the side panels, Three Male Saints and Three Female Saints. The work is by Margarito and Ristoro d’Arezzo, and is signed and dated 1274 or 1283. The small Romanesque apse which dates back to the 11th and 12th centuries is the building which, according to tradition, was miraculously brought from Asciano to the Vertighe hill.
The Crucifix in the nave on a profiled panel was painted by Lorenzo Monaco between 1415 and 1429. In the left-hand aisle, the fresco of the Assumption of the Blessed Virgin was painted in 1590 by Orazio Porta.


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