Fly into Milan and train to CT for 2 days, then rent car and head for the hills. Where would be a good place to stay to do day trips, maybe move twice?
La Crociona http://lacrociona.com/ about three minutes outside Montalcino. See Rick's book. You can drive to Siena, Pienza, Montepulciano, Bagno Vignoni, Sant'Antimo, Monte Oliveto Maggiore, Buonconvento, and Murlo. The driving is short and easy. If you want more information on this area you can e-mail me firstname.lastname@example.org
Maureen: another topic on this same section of the helpline (to the boot) discusses driving rental cars in Italy, possibly this would be of interest to you to look at the comments made by travelers who have driven in Italy.
Siena. I stayed there 4 days and it was a good base. We took buses on day trips. Stayed at Palazzo Bruchi B and B, it had access to a kitchen and was centrally located. Carmella was very helpful and speaks perfect English.