Buon Giorno! My husband and I are planning to visit Tuscany in late September. We plan to rent a car, and would like to focus on touring in the wine region. I know time is running short, and your suggestions will be highly appreciated.

Day 1: Rome-Cortona

Day 2: Cortona

Day 3: Cortona-Montepulciano

Day 4: day trip to Montalcino and Pienza

Day 5: Montepulciano-Siena (staying overnight in Siena or the Chianti region?)

Day 6: the Chianti region.

Day 7: Going to Florence? Or one more day in the Chianti region?

Day 8: Return our rental car in Florence, and take train to Rome

Day 9: Rome

Day 10: Fly out of Rome

Question 1: I've planned 2 nights in Montepulciano. Is it enough time to see Montepulciano-Montalcino-Pienza?

Question 2: As for the Chianti region, I am not sure which town is a better base -- Siena, Castellina in Chianti, Greve in Chianti?

I know we could easily spend the whole trip in just one Tuscan town and still enjoy ourselves, but we are also too tempted by the possibility of see different famous wine towns. We look forward to experiencing something like Saint Emilion in France or Santa Ynez (Santa Barbara wine country) in California. It doesn't have to be grand, but it has to be beautiful and intimate. But the problem now is... I can't really tell from reading the information.

Thank you for your time and patience. Any suggestion will be highly appreciated! Grazie!