Here is an time-based tour for one week in Tuscany with Cortona as home base. This is a good itinerary for pretty much anyone interested in exploring what Tuscany has to offer - a bit of art in both towns and major cities, great food, thermal baths and nature, and remarkable landscape.
Why Cortona? As a visitor to Tuscany, Cortona makes a great home base because you get to live the small town experience but are close to good roads. From Cortona you can easily reach the major art cities of Siena and Arezzo (40 minutes), the well known cheese and wine towns Pienza and Montepulciano (even closer), and two different thermal baths at Chianchiano or Rapolano.
Frances Mayes's Under the Tuscan Sun is set in Cortona and has made the town rather popular in recent years; here is the trailer of the movie.
We suggest that you rent a villa outside Cortona or an apartment in town for one week and just slow down, drink up the atmosphere and a good class of local red wine. Here is a suggested day-by-day itinerary that provides a nice variety of things to see, but that is also relaxing. The Tuscan lifestyle, especially in the summer and in small towns, is all about the afternoon nap while all the stores are closed, followed by leisurely strolling, a drink on a terrace at sundown...