Cortona

Cortona is still in Tuscany, but fits more conveniently into our itinerary for Umbria since it is on the route. Stop to enjoy the atmosphere of this medieval town: its narrow, twisting, cobbled streets, jumble of small squares, lovely boutiques, excellent restaurants, and colorful buildings are delightful. The heart of the town is the Piazza della Repubblica, the main square, which has many narrow streets feeding into it. If you are up for walking, climb the twisting streets to the old fortress standing guard over the town.

Review from La Mucchia Casa Vacanze and Karen Brown:

The film based on the best selling book, "Under the Tuscan Sun" was shot in the historical town of Cortona. The town with its narrow twisting streets and the surrounding geography epitomizes the Tuscan Experience. This charming town overlooks a vast fertile plain and is nestled by nearby hills and mountains. The Etruscans were the first to populate this ancient city and much of their history is still evidenced by their old tombs. The Museo dell’Academia Etrusca (Estruscan Museum offers wonderful examples of Etruscan artifacts. Cortona is also noted for its Renaissance architecture, particularly the churches Santa Maria Nuova and Santa Maria dell Grazie, both built around the 16th century.