Cortona is an incredibly ancient town and was even enclosed by stone walls by the Etruscans as early as 800 BC. Their tombs still dot the hillsides and don't understimate their cultural influence even today.
Of course, Tuscany should actually read 'Etruscany'.
To get to grips with the history first stop by two museums: the Accademia Etrusca and the Museo Diocesano.
The former is home to the incredible 'Etruscan Chandelier' dating from the IV century BC.
It was found in 1840 in the Cortona countryside and is a bronze oil lamp made featuring 16 finely decorated burners.
The historic centre of the town is, therefore, 'relatively' modern and made up of churches and Medieval and Renaissance buildings named after illustrious families.
Look out for the Palazzo Casali, Palazzo Passerini, Pallazzo Mancini Sernini and Palazzo Vagnotti.