Our first of several days in Tuscany (that is, November 5, 2023, just to give a temporal context) was supposed to be a rest day, given that we had been traveling almost non-stop for a month. But there’s no rest for the weary, and we soon found ourselves heading toward Lake Trisimeno, which we could see in the distance from our Airbnb.

After unsuccessfully looking on the internet for any trails to hike, we simply drove in the direction of Castiglione del Lago, a charming hilltop town. There were hardly any tourists or traffic, despite a very interesting castle where we were able to have a picnic lunch. We walked through the town, enjoying the medieval vibe and the lack of crowds, and then down to the lake where we walked the perimeter for an hour or so. There were lots of cafes, but everything was closed for the season. I’m sure it’s crazy in the summer.

Enjoyed getting to cook again that night – fresh papperdelle with a vegetable sauce and artichokes.

The next day we decided to tour some of the famous hill towns of Tuscany. From Cortona we drove across the valley on some seriously narrow roads with so many vistas of Tuscany hills we kept having to stop to take photos.

Ultimately we reached Pienza. The town is atop a hill, but on a flat plateau so you avoid some of the ups and downs. It too was empty at this time of year; we managed to locate ourselves on the Rick Steves audio tour and found the main square – where the grid lines of the squares line up with the palazzos to form a “Renaissance cube.” We finally found a spot outdoors where you are allowed to eat (very strict rules about this!).

We looked into some interesting – almost stark – Romanesque churches, adorned with peeling frescos on the walls. The town itself was beautifully preserved – narrow lanes, stone buildings, and what I can only call red creeper vines.

With only a few wrong turns, we drove to Montepulciano. It’s an equally charming, but much larger, hill top town. And not crowded. We were definitely experiencing the joys of the so-called “shoulder season.” We managed to situate ourselves on the map; and visited the Parroccia Santissimo Nom di Gesu – a very ornate church whose painted 3D illusions (trompe l’oeil, to use a little French), were captivating.

The main duomo, whose facade was never actually finished, was closed and booths outside were being erected for the Christmas market, to the great interest of on lookers. . We also visited the Contucci wine caves, where J bought some very expensive wine. The family still lives in their palazzo on the main square.

I especially liked the contrades building which still posted lists of births and deaths in the neighborhood. Instead of the horse races of Siena, in Montepulciano the contrades push wine casks uphill. Incidentally, this is also the place that J saw $1000 bottles of brunello.

By now it was mid afternoon, and time to make our way back to Cortona. All the wrong turns we made were compensated for by the very expensive bottle of Contucci wine.