While there is public transportation available in the countryside, it is neither flexible nor is it intuitive.
Getting from Pisa to Montepulciano by train and bus looks intimidating to me, but it is possible.
If you have some driving experience it shouldn't be a problem. There are 2 exceptions:
- Florence, small and confusing streets and the risk of being stuck in traffic for hours on end
- If you are driving you won't be able to drink ( a small glass of wine will put you right below the limit )
There should be 2 thermal centers near Montepulciano aswell, " Chianciano Terme " and " Sant'Albino "