We did a day trip out to Sienna via the train. The train is very easy and drops you at the bottom of the city. Then we took a long escalator up to the old city. We enjoyed wondering through the streets that are a bit less crowded before reaching the Piazza Del Campo. There is a great coffee shop on the corner right when you enter the old town gates.
Osteria Le Logge
Via del Porrione, 33
+39 0577 48013
Loved this restaurant. The kitchen has a large window that looks out to the streets. Just one block off of the Piazza Del Campo. Make a reservation, ask to sit on main floor.