I need some help deciding whether to go through Chianti in Greve, or San Gimignano (or both?). We would also consider Montepulciano or even Orvieto if the extra time is worthwhile. Looking for driver company service, not car rental, two adult / two luggage, early October (any recommendations?).
Orvieto is at least 1.5 hours from a Siena and worthy of a night or 2 stay
Siena itself should get more than just a quick stop
Are you staying there?
If not I don’t see how you can fit both towns plus the drive and another town in a day trip
Montepulciano is lovely and needs a few hours as well also about an hour SE of Siena
@ChristineH — thanks. Yes, staying 2 nights Siena. We would do any of the four mentioned or some combination of two. Don't mind backtracking a bit out of the way if it's a "must see" place. I'm sure all four would be too onerous.