Montepulciano is a beautiful hill town with the piazza at the very top.
Montalcino is home to Brunello, one of the finest italian wines. Both worth a stop at the very least.
For those that have bopped around Tuscany, did you rent a car to do so? It sounds like you don't want to deal with a car if you are staying within Florence and maybe even Siena, However, what about staying in and visiting some of the other smaller towns?
Thanks for the responses. In what city did you rent the car?
I am looking at a trip Venice(2 nts)-->Florence (4 nts)--> Rome (3 nights) for the wife and kid in March. The wife may be 6 months pregnant at the time if all goes according to plan, and the kid will be turning 3 in July. Is this a bad idea? Pregnant wife I think would be okay but doing Italy with a toddler does not seem like the most ideal way to go to Italy but know it will only get tougher with more kids. Flights now are pretty cheap round trip out of NY.
Thanks for the responses. In what city did you rent the car?
agree - your plan is good. 2 days in Florence is good. 1 is too rushed, 3 is too much.
if you're looking for a good small town you should check out Trequanda/Montisi/etc. They are great. Also let me know if you want a recommendation on a tour guide for Siena - we have used the same lady for years and she's great....actually edited part of the Rick Steves book.