Cortona was one of the twelve cities of the Etruscan League. Of its primitive cyclopean walls one can still look at the impressive features incorporated in the medieval walls.
Apart from a few fine Renaissance palaces, the prevailing character of Cortona's architecture is medieval, conferring on the steep narrow streets a strong atmosphere.Given its altitude (600 meters above sea level) from every point of Cortona one can  enjoy a stunning view on the entire Valdichiana.
Not to be missed: the medieval churches of S. Francis, S. Domenico, the Palazzo Casali medieval renaissance facade, the churches of S. Maria Nuova and San Niccolò, housing valuable works of art.  The "Via Crucis" Severini (XX century) accompanies the mystic ascent linking the town overlooking the sanctuary of St. Margaret, in turn dominated by the powerful Fortezza del Girifalco.  
Out of town several Etruscan tombs and Roman churches. Il Convento delle Celle, founded by St. Francis, is one of the prettiest spot in the area.
A visit to Cortona means a jump back in the 14th century, breathing traditions and tastes typical of Tuscany. Please pay a visit to the local fairs, including local food and wine tasting: you will be surprised by how old traditions arise out of such delicacies.