We are in the early planning stages of a 2016 trip to Italy. We think we will have 20 nights on the ground. Originally we were planning to fly in to Venice for 3 nights, 3 nights in CT, 6 nights in Montepulciano, 4 nights in Sorrento and 4 nights in Rome. We went to Greece this past summer, and although we loved Athens and Nafplion, we found our favorite stay was a small town south of Kardamyli - part of the reason was the amazing lodging we found, but we also enjoyed the less touristy side of the country. With that in mind, we are reconstructing our itinerary and curious what smaller, more authentic towns fellow travelers have enjoyed. My wife has never been to Italy, and I am fairly certain we are still going to visit Venice and Rome, but I think everything else is up for debate.
I have been before and visited Venice, Rome, Florence, CT, and Milan.
Thanks for any advice you have!