Spots in Cortona

Piazza Della Repubblica

This is the main piazza in the city of Cortona, and it is largely medieval in appearance. The Palazzo Comunale (town hall) dates to the 13th century with the clock and bell tower added in the 16th century. The staircase is aesthetically striking, but also functional as you can take a seat and observe life in the town center. Described by famous Dutch violinist André Rieu as “the most romantic square in Italy,” I encourage you to spend some time here and judge for yourselves.

The American comedian Conan O’Brien travelled to Cortona with Jordan, his pretentious sidekick, as Jordan claims Cortona is his favorite and ‘the most beautiful Italian city’. Conan smirks as Jordan accepts a satirical ‘honor’ (of a parking spot in his name) from these very steps. He stumbles through in rather imperfect Italian, but it is a humorous and contemporary connection to this spot, so you might want to watch the clip in anticipation of your trip. He also happens to mention La Loggetta and La Grotta as excellent restaurants in which to eat a Bistecca alla Fiorentina, and I happen to agree with this claim. (Read more about these restaurants here.) This central piazza is a good central spot from which to depart for further explorations of the town. You will want to see the adjoining Piazza Signorelli with more medieval buildings to admire. Read more here.

As mentioned, the pathways in the center of Cortona are particularly steep, but exploring them is a part of the (literally) breathtaking charm.

Santa Margherita

On the way up to Santa Margherita

You can start the journey up to Santa Margherita from the Piazza Garibaldi, specifically the recommended bar called Bottega Baracchi. A great part of the beauty in this spot is the journey up in my opinion. You walk between picturesque Tuscan homes up a narrow walkway, and views of the Chiana Valley accompany you on your way. The road you take is called the Via Santa Margherita and it will elevate your heart rate just a bit (especially if you are singing songs from Rent as we were; #theatrekids). The ascent is less than 1 kilometer and should take between 10-15 minutes depending on how many times you stop for photos.

View from the top near the Santa Margherita church

The church was originally built by Camaldolese Monks in the 11th century. The minor basilica (a status granted in 1927) has gone through major reconstructions in the last 3 centuries, but it is beautiful on the interior and exterior; it was also very quiet when we visited. The views from the top are lovely and expansive.

Diocesan Museum

Full disclosure, when I last visited Cortona it was all about relaxation, food and wine, but if you want to get your museum fix in Cortona, I suggest the Diocesan museum. It is centrally located near the Piazza Signorelli. There are two other sites in Cortona that I would recommend, the Chiesa di Santa Maria Nuova and the Fortress of Girifalco, which stands above the Santa Margherita church. Both sites are from the 16th century and very impressive, but not so centrally located. The Diocesan museum has an important collection of, especially, Renaissance paintings. Some of the highlights are described here. The most recognizable, especially if you have taken a ‘Great Works’ style art history class, is The Cortona Annunciation by Fra Angelico. The masterpiece, created between 1433–1434 , is striking (yet conventional for the style of the time) for the predominance of gold in image and text through which Fra Angelico depicts one of the most significant iconographic scenes in Christian art, that is when the angel Gabriel ‘announced’ to the Virgin Mary that she would conceive a son by the power of the holy spirit. Read more here.

Here is contact information, including opening hours for the museum.