Arezzo and Cortona: two gems of the Val di Chiana

Two ancient allies of Siena: Arezzo and Cortona

The Val di Chiana is dotted with towns of great historical and artistic value. Among these, the first is certainly Arezzo, at the confluence of three valleys and built on the hills of San Pietro and San Donato. A short distance from Arezzo rises Cortona: situated 600m above the sea level, it offers a unique view of the valley below and – on clear days – the lake Trasimeno. Both founded in Etruscan times, the two cities have flourished in the Middle Ages, when they developed a close link with Siena. Arezzo in 1260 fought at its side in the battle of Montaperti, which saw Florence defeated. The following year it was the turn of Cortona, which allied with Siena to push out the Arezzo army that had invaded the city. Subsequently, the two centers came under the sphere of influence of Florence and began to decay, although during the Renaissance they were still capable of investing in urban development.

Cortona and Arezzo: things to see

The Etruscan and Roman past of Arezzo is testified by valuable artefacts kept in the local archaeological museum. The city reached the height of its splendor in the Middle Ages, and not surprisingly most of its churches and its buildings dates back to this period. Among these is the church of San Domenico, that holds cross painted by Cimabue and the Basilica of San Francesco, with frescoes in the apse by Piero della Francesca featuring the Stories of the True Cross. Also worth mentioning, the church of Santa Maria Assunta, which boasts an altarpiece by Pietro Lorenzetti, or the Duomo, with works by Piero della Francesca and Donatello. Also the subsequent eras have left traces in the city, such as the Renaissance sanctuary of Santa Maria delle Grazie and the Lodges designed by Giorgio Vasari. And in Cortona, what to visit? Whe can start with the archaeological park that bears witness to the Etruscan origin of the city. We can continue with the many precious religious buildings, such as the Duomo and the medieval church of San Francesco. You shouldn’t also miss the impressive monastery of the Carceri, founded by San Francesco, and the church of Santa Maria delle Grazie al Calcinaio: designed by the Renaissance architect Francesco di Giorgio Martini, often shrouded in mist during the fall, leaving only a glimpse of the dome that semms to be suspended in emptiness.

Visiting Arezzo and Cortona

Arezzo and Cortona are two easy to reach destinations for those who stay in Siena. Arezzo is about 80 km from the city of the Palio and is well connected by buses and trains. From Arezzo you can easily reach Cortona moving about 30 km, by car or by public transport, in this case train and bus. We also recommend arranging the visit in order to coincide with one of the major events organized by the two cities. In Arezzo, every first Sunday of the month, you can visit the antiques fair with exhibitors from all over Italy that animate the streets of the city center. Every third Saturday of June and the first Sunday of September you can enjoy the Giostra del Saracino: a suggestive historical procession through the streets of the cetner followed by the exciting re-enactment of a medieval tournament. The best time to visit Cortona is, however, between late August and early September, in order to visit the Cortonantiquaria: in the splendid Vagnotti palace, dozens of antique dealers put exceptional pieces on display, from furniture to sculptures, from paintings to jewelry.