Hi everyone! I am considering a 4 night break, staying at the Garden Hotel in Siena. We are thinking of visiting Cortona, San Gimignano and Montepulciano. Can anyone else recommend worthy sites? We will be hiring a car, and walking around is not an issue for us either!
The list you have will already completely fill up 4 days --- remember you want to leave something for visiting Siena!
Have a look at this link, there are several good itineraries which you could experiment with for Siena -- including this article which specifically suggests several places fairly close to Siena.
On you travels to Montepulciano, you can try to incoporate:
