I have always taken public transportation in Europe (buses, trains, bikes, and even planes), but my mother wanted to try renting a car

so we could enjoy some of the smaller towns in Tuscany.  We picked it up on August 5, 2015, in Orvieto.

Since we were not picking up our rental car until 10:30 am, we enjoyed the nice breakfast buffet at Hotel Duomo.  They had pastries, toast, yogurt, fresh blackberries (!), and even blood orange juice!

We walked through town then took the funicular back down to the train station.

It was much less crowded than when we arrived!

We enjoyed the views while riding the funicular!We even passed the other funicular car on the way down!  It was so much like last year in Lugano or on the Peak Tram in Hong Kong (but not that steep).
We picked up our Hertz rental car two blocks from the Orvieto train station.  (We got an Alfa Romeo Giulietta instead of the expected Fiat.)  Our first stop was Montepulciano.  We parked in parking lot P5 (behind the bus station) and took the public elevator up.

(We parked in a white spot, which was probably free parking, but we paid at the parking meter just in case.)

We entered the old town at Porta al Prato.

Montepulciano reminded me so much of Mont St. Michel and Les Baux de Provence!

Piazza Grande in Montepulciano was under construction, but I got some pictures with its buildings, Palazzo Communale (left) and the Duomo (right).
We hiked up to San Francesco in Montepulciano for a nice view, then we started making our way down.

We stopped by a little grocery store (alimentari) and got a bag of croissants and some cold pop for lunch.  Yum!

From Montepulciano, we drove to Pienza, where we snagged a great parking spot across from the Coop grocery store.
Pienza is small but has nice views of the nearby countryside.  It reminded me of a combination of Trogir, Croatia, and Frankenmuth, Michigan. We grabbed some gelato to enjoy while strolling in Pienza!
From Pienza, we entered our most stressful session of driving: Siena!  Yes, follow the soccer ball signs to the Stadio parking.  It only took us three loops around to follow the signs correctly and a three-point U-turn when we overshot the entrance to the lot.  Then the spaces were tiny!  But we found this great spot right next to the stadium.  I should never complain about US parking lots again! The walk to our hotel, Albergo Bernini, from the Stadio parking lot was not very far.  Albergo Bernini is right on a main tourist thoroughfare.  We paid 85 euros per night ($94) + tax + 5 euros per person per night for breakfast.
Our room was spacious but sparsely furnished.  It had two comfy beds, a big closet, two nightstands, great air-conditioning, a desk, and a chair or two.  My mother said it reminded her of an old Southern bedroom.  (Only a limited number of towels were provided, though.)  It was all we needed.Our room was ensuite with a shower, toilet, sink, and bidet.  I prefer showers with curtains because they are less constricting.  This shower curtain did not keep the water in, though, so I flooded the bathroom whenever I took a shower.  Also, the soap provided is a one-day soap; with the language barrier, we were given liquid hand soap instead of another bar, but we made it work!
For our first dinner in Siena, we just went to touristy Ristorante San Domenico around the corner from our hotel.  It had a busy waitstaff, a pretty view, and yummy pizzas.  I had the sausage and onion pizza--delicious!

(The only negative: smokers!  I live in a non-smoking world in the U.S., and it was quite shocking to have to eat with people smoking all around us. It was not appetizing.)