We woke up on day 11, Wednesday, October 9th – our last day in Tuscany – ready to attempt another drive in our rental car, this time to the south. We were feeling adventurous, and had the towns of Pienza and Montepulciano in our sights. The farther of these towns, Montepulciano, was about an hour from Siena. This time, before leaving, we had a lengthy discussion with the hotel manager regarding the proper route back in to the city, which proved to be immensely helpful to us later in the afternoon.

Glenn, at breakfast on Day 11:

With so many towns to visit and only one day left, I was a bit worried about my choices for this final day. As it turns out, both Pienza and Montepulciano were great towns to tour, and we loved both of them.

We stopped first in Pienza, which is a UNESCO World Heritage Site, but before I tell you about the town, I just have to say that the drive over to it was beautiful. The drive takes you through the Val d’Orcia, which is a geographic region that is actually a UNESCO World Heritage Site in and of itself. If you picture in your mind the postcard view of Tuscany, that is the Val d’Orcia. Gently rolling hills dotted with the occasional clump of cypress trees are what defines this area.

As for Pienza, this was a really beautiful little town with an interesting history (aren’t they all?). Formerly known as the village of Corsignano, the town got a makeover when a former resident by the name of Aeneas Silvius Piccolomini became Pope Pius II. The pope had the entire village rebuilt (somewhere around 1459) as an ideal Renaissance town, with the intention of using it as a retreat from Rome, and the Vatican. When we were there it was a gorgeous little village to walk through (no cars allowed), with sweeping views of the Val d’Orcia from the walls of the town.

We had an enjoyable lunch at an outdoor trattoria called Latte di Luna, and then headed to the car park. Our next stop was Montepulciano, eight miles to the east.

Montepulciano is a much bigger town than Pienza, and like the other hilltop towns of Tuscany, you can see it long before you arrive. The town sits high upon a limestone ridge almost 2,000 feet above sea level.

No cars are allowed here either, so we parked the car on the edge of the town and set out. The weather turned slightly uncooperative at this point, and we were treated to another afternoon rain. We found a coffee shop where we could wait it out, and went in and had a seat at the bar. It was kind of interesting, this was the only place so far on our trip where I felt really remote and far from any English-speaking people, and I wished that I’d taken a bit more time to study Italian.

We wanted to make sure that we got back to Siena before dark, given the driving experience (debacle) that we’d had a couple of days before, so we said goodbye to Montepulciano and steered the car back to Siena. We made it home with no trouble this time, and with perfect timing. As we settled in to comfortable chairs on the garden patio of our hotel, which overlooked the valley, we were treated to a spectacular sunset.

Bella Tuscany.