Any proper tour of Cortona begins with piazza della Repubblica and piazza Signorelli, which used to be one space before the 13th century and also the site of an Etruscan-Roman forum.
Both are home to many medieval buildings, like the town hall at the southern end and the area known as Croce del Travaglio at the northern end. The town hall, dating to 1236, dominates piazza della Repubblica, while on the other side of the square sits Palazzo del Capitano del Popolo, from the 14th century and the former residence of cardinal Passerini. In the nearby piazza Signorelli is Palazzo Casali, also known as Palazzo Pretorio. Since 1728, the building was home to the Accademia Etrusca and is now the site of a museum, the library for the municipality and the Accademia Etrusca, as well as the town’s archives. The two underground floors of the palazzo, which once used to be used as a prison, are now home to the Etruscan Academy Museum and the Museum of the City of Cortona. In the same piazza, to the right of Palazzo Casali, you’ll find the Teatro Sigorelli. 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 the theatre leads to piazza del Duomo, where you can admire the Renaissance cathedral that was built atop the older Church of Santa Maria. Palazzo Vagnotti is located next to the cathedral, which served as the headquarters of the bishopric seminary and is traditionally where the antiques fair is held.
The area known as Croce del Travaglio begins in via Dardagno, one of the most characteristic 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’ll find the monumental Church of San Francesco and its adjacent convent. This area is traditionally known as “Bagno della Regina,” and was perhaps home to ancient Roman thermal baths. Continuing up via Berrettini, you’ll come to the upper part of the town, where there are many typical streets, each pretty and 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 drinking water, though you won’t see it as you explore the piazza. Higher up is piazza della Perscaia, which gets its name from the Roman water cistern that the Convent of Santa Chiara was built over 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 16th 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 probably follows the ancient Decumano street that was laid by the Romans when they settled area. This road, which ends at Porta Santa Maria, is where you’ll find Palazzo Cinaglia, with its characteristic Dead Man’s Gate and the Baroque Church of San Filippo (1690 – 1728), home to a Madonna and Child with Saints by Piazzetta (1739 – 1743).
Outside the city walls, about 2km from Cortona along the road that leads to Camucia, is an interesting Renaissance church with the painting Madonna del Calcinaio by Francesco di Giorgio Marini (1485 – 1513). The church also conserves an Annunciation from the Signorelli school and an Assumption by Papacello. Travelling north about 3km is the Convent delle Celle, surrounded by breath-taking countryside. The convent was founded by St. Francis between 1211 and 1221, and the cell where the saint stayed for a time is open to visitors.