Cortona is believed to be one or if not the oldest known settlements on the Italian peninsular, predating Roman civilization by several hundred years this town was one of the main centres of the Etruscan civilization. Today it is probably one of the most visited cities in the area as it is stunningly beautiful with fabulous views of the countryside along the medieval town walls.
Great for an Aperitivo is a bar in Cortona called Tuscher Hall, owned by Massimo
Pane e Vino is very good spot for lunch
Snoopy serves great gelato and even better for people watching as the square in which it sits becomes the centre of the towns night life
For dinner Il Teatro (the theatre) is elegant and casual all rolled into one with
owner’s wife having the more outrageous laugh!
You can eat outside under a renaissance loggia in the main square at La Loggetta and watch the town go by of an evening. http://www.laloggetta.com/en