There are many places to visit around Cortona. Montepulciano, just a 20 minute drive from the Villa is know throughout the world for it's wine. Wine connoisseurs consider it's Vino Nobile among Italy's best. The medieval town stands on the top of a hill with amazing views of the Val di Chiana. There are many places to eat and taste wine in the town and in the countryside surrounding it.
Siena, a 45 minute drive holds the famous Palio twice a year in July and August. The city has many churches, museums, gardens open to the public and a market every Wednesday morning.