On Day 5, we left Siena, drove to San Gimignano, and ended up in Volterra.

After breakfast in Siena, we checked out of our hotel, paid for our parking, and drove to San Gimignano.  We parked in big parking lot P1 south of town and walked in.  This is Porta San Giovanni. San Gimignano was like a combination of Mont St. Michel, Macau, and all the other Tuscan towns we had visited.  Here I am in Piazza della Cisterna, with its central well.
We followed the signs up the steep hill to the Rocca e Parco de Montestaffoli for stunning views of the nearby countryside.  We could see so far!
More countryside views from San Gimignano. Looking back at some of San Gimignano's famous towers.
More views of San Gimignano's towers Gelato stop in San Gimignano!  (This was one of the only places where we got a wafer.)
From San Gimignano, we drove to Volterra.  We parked in the tight underground parking garage (which was hard to find) and walked through town to our hotel, Hotel La Locanda.  It is only a couple of blocks from the view terrace of the Roman theater!  It was also the cheapest hotel we stayed at on our trip [83.70 euros ($92)] (and Volterra has no tourist tax!). We got a giant room with two beds, a big closet, a desk, and a minibar.  The air-conditioning was also good.  The soft drinks in the minibar (a Coca Cola and a Fanta) were free on arrival, and they really hit the spot!
The bathroom was also *very large,* with a shower, toilet, bidet, sink, and *lots* of towels! We followed the Rick Steves self-guided walk of Volterra.  It starts at this amazing Etruscan arch (Porta all'Arco) from circa 4th century BC.  The plaque on the right commemorates when the townspeople saved the arch from the Nazis in 1944.
The highlight of Volterra, for me, was seeing their remains of their Roman theater.  It's free to look at and still has some of the theater wall.  WOW!  I was so impressed.  It was not expected!It was so fun to see the Roman theater!  It reminded me so much of Arles, France--and another tourist passing by said the same thing!
We were up at the top of the theater and walked down the stairs and around to get this different view.  There is even an in situ mosaic floor from when the theater was turned into a baths! We wandered around town more, went to look for an alabaster workshop (which was closed), and enjoyed sitting on a bench in the Archaeological Park (where you can peek through the fence at Etruscan acropolis ruins), then decided on dinner at Pizzeria Il Rifugio after reading several menus.
I had the delicious hand-made ravioli in truffle cream (serving didn't look large, but it was very filling!). My mother had the hand-made gnocchi with mozzarella and tomatoes, which she liked.
We walked around town more after dinner and enjoyed this beautiful red sunset.