ABOUT CORTONA TOWN

Cortona is a charming Tuscan hill-town that may soon become one of your favorites. Nestled amidst olive groves and vineyards, it offers breathtaking views of Lake Trasimeno and the Valdichiana plain. Despite its two notable galleries and several churches, it remains relatively undiscovered, making it an ideal destination for those seeking a peaceful getaway. The town’s medieval streets are a delight to explore, and it also offers a variety of accommodation options, including charming B&Bs, apartments, hotels, and restaurants, making it a great place to spend the night.

Cortona is also steeped in history and legend. According to tradition, it was founded by Dardanus, the founder of Troy and the namesake of the Dardanelles. The story goes that while fighting a local tribe, he lost his helmet (corythos) on Cortona’s hill, and the town that grew up there took its name (Corito) from this missing headgear. The Etruscans built the first set of town walls in the 4th century BC, and traces of these can still be seen in the present fortifications. As a member of the Etruscans’ 12-city Dodecapolis, Cortona was one of the federation’s leading northern cities. Its importance was further maintained under the Romans due to its proximity to the important consular road, the Via Cassia.

However, Cortona’s fortunes waned during the Middle Ages as the plain below turned into marshland. Despite resisting neighboring cities such as Perugia, Arezzo, and Siena, the comune was captured by King Ladislas of Naples in 1409 and sold to the Florentines two years later.

The steep streets of Cortona may require some effort to navigate, but the views and charming medieval scenes are well worth it. The only exception is the main Via Nazionale, referred to as the “Ruga Piana” or “Flat Street” by locals, which connects Piazza Garibaldi and Piazza della Repubblica.

When exploring the old town of Cortona, be sure to visit Via Guelfa, Via Ghibellina and Via Janelli for a glimpse of a mixture of medieval and Renaissance architecture. Via Janelli, in particular, is a picturesque street lined with 14th-century timber-framed houses, located just below Piazza del Duomo. Another must-see is Via Maffei, which boasts a parade of 16th-century Renaissance palazzi.

The church of San Francesco, located on Via Maffei, is notable for being the first church established by the Franciscans outside of Assisi. Inside, the third altar on the left (north) wall features an unfinished Annunciation painting from 1669 by Pietro da Cortona. While the painting is considered a poor representation of the artist’s best work, which can be found in various Rome’s baroque churches and the Palazzo Pitti in Florence, the ceiling frescoes in the Palazzo Pitti brought the artist fame. The church’s crypt is also believed to contain the tomb of another famous painter from Cortona, Luca Signorelli (1441-1523).

The church of San Francesco, located on Via Maffei, is a notable destination for its historical and artistic significance. It was the first church established by the Franciscans outside of Assisi. Inside the church, the third altar on the left (north) wall features an unfinished Annunciation painting from 1669 by the famous artist Pietro da Cortona. This painting is considered to be a less impressive representation of the artist’s best work, which can be found in various Rome’s baroque churches and the Palazzo Pitti in Florence, where his ceiling frescoes brought him fame. Additionally, the church’s crypt is believed to contain the tomb of another famous painter from Cortona, Luca Signorelli (1441-1523).

Make sure to include a trip to the cypress-lined San Nicolò church. The church is known for its double-sided painting by Luca Signorelli, one side depicting a Deposition and the other a Madonna and Child. Ask the custodian to demonstrate the pulley system that rotates the painting.

Another must-see is the old church of San Domenico, where a faded fresco by Fra Angelico can be found above its portal. Inside, a chapel to the right of the high altar showcases a Madonna and Saints painting by Signorelli and a detached fresco of San Rocco by Bartolomeo della Gatta.

The altarpiece, The Coronation of the Virgin (1402) is by Lorenzo Gerini. To the east of the church, visitors can take a stroll in the lovely Giardini Pubblici, also known as “Parterre”, which offers beautiful views.

Santa Maria del Calcinaio

Located just 2 miles from Porta Sant’Agostino, the 15th-century Renaissance church of Cortona is a must-see.

It is situated on a winding approach road and was built on the site of a tannery (known as a Calcinaio due to the lime used in the tanning process) to house an image of the Virgin that had miraculously appeared on the tannery walls.

The church is built on a Greek cross plan and features a central dome, similar to other High Renaissance churches in Prato, Montepulciano, and Todi (in Umbria).

Views

For the best views of Cortona, be sure to visit the Fortezza Medicea and the public gardens near San Domenico. To truly appreciate the stunning vista, come at dusk, when the lights from the vast plain below the town twinkle in the background.

Hannibal

ust a few miles east of Cortona, at Tuoro sul Trasimeno, visitors can explore the site of one of antiquity’s most renowned battles. In 217 BC, Hannibal and his army successfully ambushed and defeated a Roman army led by consul Flaminius, resulting in the death of 16,000 Romans. The site can be accessed by car and a marked trail has been created for visitors to explore.