San Gimignano is a wonderful Tuscan hill town, with more of it’s tower houses left than any other similar town. It’s a wonderful place to visit both for views of it, and from it. There is also a fabulous Gelateria(ice cream shop) in one of the squares.
Sienna is known for Porchetta (roast pork loin) rolls, and in the west corner of the Palio is Salumeria Il Cencio. They have some benches on the first floor with a wonderful view across the Palio. They are reached by this interesting spiral staircase. You can see the benches on Google Earth, if you look closely enough.