Visitors should begin their tour of the town in Piazza della Repubblica and Piazza Signorelli. Until the thirteenth century these two squares were in fact one space and also the site of an ancient Etruscan-Roman forum.
Both are framed by public and private medieval buildings. The Palazzo Comunale (Town Hall) sits at the southern part of the square and the area known as Croce del Travaglio delimits the northern edge.
The Palazzo Comunale, which dates back to 1236, dominates Piazza della Repubblica. Opposite is the fourteenth century Palazzo del Capitaino Popolo which used to be the official residence of Cardinal Passerini.
In the adjacent Piazza Signorelli is Palazzo Casali, otherwise known as Palazzo Pretorio. Since 1728 this building has been home to the Accademia Etrusca and now houses a museum, the municipal and Accademia Etrusca’s library, as well as the town’s historical archive. The two underground floors of the palazzo, which once used to be used as a prison, are now home to the Museo dell’Accademia Etrusca (the Museum of the Etruscan Academy) and the Museum of the city of Cortona.
In the same square, directly to the right of Palazzo Casali, is the Sigorelli Theatre. This theatre was built between 1854 and 1857 by Carlo Matteschi and was commissioned by the Accademia degli Arditi. The road between Palazzo Casali and Signorelli Theatre leads to Piazza Duomo where visitors can admire the renaissance cathedral which was built on the ancient Santa Maria church. Next to the cathedral is Palazzo Vagnotti which was headquarters of the bishopric seminary and traditionally where the antiques fair is held.
The area known as Croce del Travaglio begins in Via Dardagno which is one of the most characteristic streets in Cortona. At the end of Via Dardagno, beyond the Colonia Gate, the road goes down to Santa Maria Nuova church. The construction of this church was started by Cristofanello in 1550 and then completed by Giorgio Vasari.
From Croce del Travaglio, in Via Benedetti visitors can appreciate Palazzo Fierli-Petrella. Up the nearby Via Maffei is the monumental San Francesco church, a complex which includes the church and the convent. The area where this church and convent are built is traditionally known as ‘Bagno della Regina’ and was perhaps home to ancient Roman thermal baths. Continuing up past San Francesco church on the Via Berrettini we reach the upper part of the town. In this area there are many typical pretty narrow streets and medieval buildings. In Piazzetta del Pozzo Caviglia there used to be a natural spring with drinking water. Higher up is Piazza della Perscaia which takes its name from the Roman water cistern which the Santa Chiara convent was built on by Giorgio Vasari. On the opposite side of the piazza is San Cristoforo church which contains the chapel of the nativity dating back to the sixteenth century.
The round church of San Benedetto is on a street that crosses Via Guelfa. This church contains an interesting wooden statue known as ‘Cristo alla Colonna’. There are several characteristic medieval houses opposite. Other medieval houses can be seen in Via Jannelli and these have the particular characteristic of having wooden beams throughout their upper floors. Via Roma probably follows the ancient Decumano street that was laid by the Romans when they settled the area. This road, which ends at the Santa Maria Gate, is home to Palazzo Cinaglia with its characteristic ‘Porta del Morto’ (literally ‘Dead Man’s Gate’) and the Baroque church of San Filippo (1690 – 1728). This church contains a ‘Madonna and Child with the Saints’ (1739 – 1743) by Piazzetta.
Outside the city walls about 2kms from Cortona along the street that leads to Camucia, is an interesting renaissance church with the painting ‘Madonna del Calcinaio’ by Francesco di Giorgio Marini (1485 – 1513). Apart from the ‘Madonna del Cacinaio’ (fourteenth to fifteenth century), inside the church there is also an Annunciation from the Signorelli school and an Assumption by Papacello.
Travelling north, about 3kms from Cortona is the Convent delle Celle, set in breathtaking countryside. This convent was founded by San Francesco between 1211 and 1221 and the cell where the saint stayed for a time is open to visitors.