Cortona and its typical flagged streets is a city with a strong medieval taste, easily seen from the first step made on the main street traditionally called "Ruga Piana".
It is built on a buttress of Monte Sant-Egidio, and is surrounded by a massive rectangular wall.
The landscape is that of Tuscany : a fusion of art and nature, of new and old, to make up a harmonious whole. Looking from the top of the city walls, one can see one of the finest and widest views in Italy, the wide fertile plain of the Val di Chiana, with the mountains of Siena at the far end, Monte Amiata and Monte Cetona standing out, and the great shining expanse of Lake Trasimeno .
The road from the plain to the city winds through terraced olive groves divided by dry stone walls with fine villas surrounded by pines, ilexes and cypresses, farms, monasteries and monumental churches which seem out of place in this isolation, in pure Renaissance style with domes, windows and belfries all in the light-colored local stone.

One can see that Cortona was a power in Etruscan times by the massive walls of which many traces remain. Many Etruscan tombs have been discovered in the countryside beneath. The most famous are: the "Tanella di Pitagora"(V century BC), and « Melone » at Sodo.
There is a wealth of exhibits in the Etruscan rooms of the Museum in Palazzo Casali, with jewellery and artefact such as a famous, richly embossed bronze lamp, of the V century BC, found in 1840. Palazzo Casali has a Renaissance façade; it houses the Museum of Etruscan Academy, with Etruscan, Roman and Egyptian collections, and a picture gallery with works by Pinturicchio and Luca Signorelli. In the same building, a valuable library is located.

On the top of the hill, the ancient Medici fortress.

One of the most important of the older buildings is the Palazzo Civico of the XIII century, with Its XVI century tower. Other fine buildings are: Palazzo Fierli Petrella of the XV century; Palazzo Ferretti of the XVIII century; Palazzi Lovari and Mancini by Brunelleschi, Palazzo Mancini-Sernini, and Villa Passerini, called also the « Palazzone » built by G. B. Caporali about 1515.

Of the churches, to be noted: Sant'Agostino (late XIII century); San Domenico (XV century); San Francesco, begun by Brother-Elia in 1245 with Romanesque and Gothic features; the Abbey of Farneta, Pre-Romanesque; the Abbey of Sant'Angelo.
The Sanctuary of Santa Margherita was founded by the Saint herself in the XIII century but it was completely rebuilt in the XIX century with the Gothic tomb of the Saint, of 1362.
The church of Santa Maria delle Grazie was begun in 1485 by Francesco di Giorgio Martini.
The Renaissance church of Santa Maria Nuova is of 1550 and the Cathedral, which was first built in the XI century, was rebuilt at the end of the XV century. The campanile is dated 1556.
The XVI century church of San Niccolò has a fine painted banner by Luca Signorelli.
The church of the Gesù houses the Diocesan Museum, with a number of important paintings including Beato Angelico's famous « Annunciation ». Nearby is the Capuchin Convent « le Celle », founded near the cell in which St. Francis of Assisi lived.

Cortona was the birthplace of Luca Signorelli and Pietro da Cortona.

The Communal Library is world-famous. It contains 22,000 printed volumes, 1172 parchments, 133 incunabula, and 633 manuscripts.