Although not required, an elementary course or some sort of self-instructed program in Italian is highly recommended before your trip to Cortona. At the bare minimum, learn several basic phrases (directions, questions) and the numbers before you go. It will help ease the "culture shock" during the first few days. A phrase book and a paperback English/Italian dictionary are essential.
Italians appreciate the effort shown by foreigners when they try to speak Italian. They are more apt to be receptive and helpful to you if you try to speak to them in their own language.
Read as much as you can about Italy before you go. It will help you to understand and appreciate what you see and hear. See the bibliography on the last page of this handbook for some basic recommended reading.