Cortona suggestions

My wife and I are to travel to Cortona for 5 weeks in October, 2016.  Any suggestions for what we really must do while there, in terms of connecting locally, sites, food, wine, travel in Tuscany, Umbria, Rome, etc?

Thanks.  We also hope by then to be able to converse some in Italian!

Bob

My family and I spent three weeks in Rome, Spoleto and a very small town in Calabria last summer. I would highly recommend that you spend a lot of time getting to know Cortona. Every little street will hold some treasure waiting to be discovered and enjoyed. When not in Cortona, spend time driving, or better yet riding a bicycle, through the countryside, stopping in at very small towns and sitting in a cafe on the piazza to enjoy a cup of coffee or glass of wine while talking to the locals. We spent a day in Siena and a day in Firenze as part of our trip and found them to be so crowded (Firenze in particular) that it was hard to enjoy them. Plus you're likely to hear almost as much english in those main tourist cities as you will italian. We may return to Italy again this autumn. If so we'll go back to Rome for a couple of days but we'll give the other main tourist destinations a miss.  The Tuscan countryside is spectacular and Umbria is very pretty as well. The food is to die for, the wine is fantastic and the people are extremely nice. If you don't try to do too much and just try to enjoy living like an italian as much as possible, you will have a wonderful time.