Italy in Two Weeks
 

My husband and I will be traveling to places in Italy that we have not traveled in the past. the basic 2-week itinerary is as follows: Rome, rent a car to see the Hill Towns traveling through Umbria(perhaps Orvieto), Tuscany (Montalcino, Montepulciano, Cortona, and Siena, Chianti?). Two nights in Florence, plane to Sicily and stay 3 nights in Taormino with day trips to Agrigento and Syracuse, then to the Amalfi Coast staying in Positano. The final night will be in Rome to fly back to the States. Are we biting off too much? My greatest joy will be the Hill Towns - can anyone suggest the best itinerary to drive, see the wine country, shoot photographs and have a relaxing time through this area? I want to linger and not rush, I'd rather concentrate on a few wonderful experiences rather than see it all. I would prefer quaint and untouristy, middle of the road expense, Yes, I have read the blogs - if it's easier to point me to a particular posting of someone that has loved a particular journey such as this - please do. We're very adaptable! Thank you for taking any time to help out.

Barbara

Yes, I do think that is too much.
I would drop either Sicily, which deserves 2 weeks, or the AC.
Asssumimg 13 nites to sleep in Italy, I see:

Tuscany/ Unbria--5
Rome---4
AC OR Sicily--4
That is a FULL 2 week trip---save Sicily when you have more time.

Absolutely what Bob said!

Even if you still include Sicily, it is a long day from Taormina to Agrigento and back.

I suppose you don't want to visit Rome, but you just start from there, otherwise your plan is unworkable. I think that the time in Sicily is really short for doing the daytrip to Agrigento and Syracuse. Maybe you can rent a car there and spend a night on the way, but in this case you have no time for Taormina.
About the Hill-towns, if the first time, I suggest you to visit the most known sites as : from Rome > Spoleto > Spello > Assisi > Perugia > Todi > Orvieto > Pienza > Montalcino > Siena > San Gimignano > Firenze. This is a reasonable itinerary that needs 10/11 hours slow driving and you can divide in few days.