During the XII and XIII centuries, Cortona was a prosperous autonomous community. It then passed into the governing hands of the noble family of Casali under which it became the Bishops seat in 1325 and also became a part of the Florentine state in 1411. It was the home of many illustrious men, among them Luca Signorelli, Brother Elia Coppi, Pietro Berettini, Gino Severini just to name a few. The actual look of Cortona is characterized by wide usage of the local sand stone in the steep and narrow streets and alleys with an abundance of breathtaking views of the Val di Chiana below as well as many examples of perfectly conserved Medieval and Renaissance buildings, lending a general feeling of walking through history. All surrounded by the ancient city walls. Do not forget the medieval church of Saint Francis, built by Brother Elia Coppi, which houses a reliquary of the true cross. Interesting also is the church of Saint Domenic (XV century) with its famous poliptic by Nicolò Gerini.

One can also see the beauty of the church of Saint Ausustine from the XIII century (now under restoration) and the city building-Palazzo Comunale-which dates back to the XIII century. Palazzo Casali, the one-time seat of the Nobility of Cortona and today the home of the Museum of the Etruscan Academy and the Etruscan Academy itself, with the facade renovated in the XVII century by Filippo Berettini. The Palace of the People now Palazzo Passerini, one of the oldest buildings in the city. The Renaissance Testimony of the Sanctuary of Madonna delle Grazie in Calcinaio, Designed by ùFrancesco di Giorgio Martini is also important. It is situated at the base of the hill which makes up Cortona and is in the shape of a Latin Cross with an octagonal dome. On the other side of the hill is situated the twin church of Santa Maria Nuova. In the upper part of Cortona known as Poggio one can find the church of Saint Nicolas with a processional banner (now altarpiece) by Luca Signorelli. The Duomo is situated on top of the ancient Romanesque Church of Santa Maria.

Many are the palaces of the nobility especially in the historic center and the grandiose Medici fortress on the top of the hill. A little below is the Basilica of Santa Margherita in which rests the whole mummified body of the Saint who died in 1297. In the area a must-see is the Abbey of Farneta that today houses also a small museum of Paleontological and archeological materials from the immediate area. Of interest also are the church of Saint Michael in Metelliano and the Franciscan Monastery of Le Celle. The Diocesan Museum is worth a visit with the works of Luca Signorelli, Beato Angelic, Bartolomeo della Gatta, Sassetta, Pietro Lorenzetti and other sacred works.

The Museum of the Etruscan Accademy houses an important Etruscan collection, a part of which is the famous Lamp, Roman and Egyptian artifacts and urns, Paintings and minor works of art of the XIII to the XVIII century and several works donated by Gino Severini to the City. Also to be seen in this excellent museum are the precious discoveries of gold which were discovered in the Etruscan tomb of Melone II in Sodo. There are continuous activities and cultural entertainments of Folklore, a live theatre season at Teatro Signorelli in January, The Feast days of the Patron Saint Margaret in February, The Good Friday procession with the statues of the passion of Christ, the Festival of Copper in April, The Archidado – a medieval festival with crossbow competition in May which re-enacts the historic marriage between Francesco Sensese Casali and Antonia Salimbeni. Among the most important activities in Cortona are the Antique Furniture Show and the Traditional Festival of Steak that take place in the month of August.