Our tour of Cortona begins with Piazza della Repubblica and Piazza Signorelli, the site of an Etrusco-Roman forum, where the cardo (north-south street) and the decumanus (east-west road) converged at right angles.
The current area is divided into two piazzas, Piazza della Repubblica and Piazza Signorelli, which are framed by a series of public and private medieval buildings, bookended by the town hall to the south and the area known as Croce del Travaglio to the north. The town hall, which dates to at least 1236, looms over Piazza della Repubblica, while on the other side of the square sits the fourteenth-century Palazzo del Capitano del Popolo, the former residence of Cardinal Passerini. In the nearby Piazza Signorelli is Palazzo Casali, also known as Palazzo Pretorio. Since 1728, this building has been home to the Accademia Etrusca with its adjoining museum, two libraries – its own and the town’s –as well as the civic archives. The two underground floors of the palazzo, which once served as a prison, are now home to the Museum of the Etruscan Academy Museum and the City of Cortona. In the same piazza, to the right of Palazzo Casali, you find the Teatro Signorelli, which was commissioned by the Accademia degli Arditi and was built between 1854 and 1857 by Carlo Matteschi.
The road between Palazzo Casali and the theatre takes you through Piazza del Duomo, where you can admire the cathedral that was built in a Renaissance style atop the older Church of Santa Maria.
Palazzo Vagnotti is located next to the cathedral, which served as the headquarters of the episcopal seminary and is traditionally where the antiques fair is held. The area known as Croce del Travaglio begins in via Dardano, one of the most distinctive streets in Cortona. At the end of it, beyond Porta Colonia, the road goes down to the Church of Santa Maria Nuova, which was begun by Cristofanello in 1550 and later finished by Giorgio Vasari. From Croce del Travaglio, in via Benedetti, you can admire Palazzo Fierli-Petrella, while up the nearby via Maffei, you find the historic Church of San Francesco and its adjacent convent. This area is traditionally known as “Bagno della Regina,” (the Queen’s bathhouse) and was likely home to ancient Roman thermal baths. Continuing up via Berrettini, you reach the upper part of the town, where there are many typical streets, each charmingly pretty, narrow and lined with medieval buildings. The curious name of Piazzetta del Pozzo Caviglia comes from the fact that there used to be a natural spring with safe drinking water here, sadly no longer to be found. Higher up is Piazza della Pescaia, which takes its name from the Roman water cistern over which the Convent of Santa Chiara was built by Giorgio Vasari. On the opposite side of the piazza is the Church of San Cristoforo, which contains the Chapel of the Nativity, dating to the sixteenth century.
The central-plan Church of San Benedetto is on the street that crosses via Guelfa. This church conserves an interesting wooden statue known as “Cristo alla Colonna” and stands opposite several characteristic medieval houses. Other similar homes can be seen in via Jannelli, which have typical wooden beams throughout their upper floors. Via Roma likely follows the ancient decumanus that was laid when the Romans settled the area. This road, which ends at Porta Santa Maria, is where you find Palazzo Cinaglia, with its distinguishing “Dead Man’s Gate” and the Baroque Church of San Filippo (1690 – 1728), home to a Madonna and Child in Glory with Saints by Piazzetta (1739 – 1743).
Outside the city walls,about two-and-a-half kilometres from Cortona on the road that leads to Camucia, there is an interesting Renaissance church with the painting Madonna del Calcinaio by Francesco di Giorgio Marini (1485 – 1513). The church also preserves an Annunciation from the Signorelli school and an Assumption by Papacello. Travelling north by about 3 km, you come across the delle Celle Convent, which is surrounded by breathtaking countryside. The convent was founded by Saint Francis between 1211 and 1221, and the cell where the saint stayed for a time is open to visitors.