Last Updated on 02/10/2023
It’s hard to beat the beauty of Tuscany with its rolling hills, cypress lined roads and hilltop towns. As much as I love visiting Tuscany in summer to see the sunflowers and eat gelato, there’s something mysterious and special about Tuscany in winter.
On the way down from Venice and Verona, I decided to stop in Pienza (for pecorino among other things). The Val d’Orcia in southern Tuscany is certainly a gem of the region. It’s known for those picturesque scenes of cypress trees lining country roads and local pecorino.
While I’ve visited Tuscany many times, I’ve never seen it quite like this…. It was absolutely a ghost town! I went in the middle of the week, and not much was open to be honest with you. While most of the restaurants are not open on weekdays, they operate as normal on the weekends. I would recommend planning your trip so that you are in the smaller towns on the weekends and larger cities like Siena or Florence on the weekdays.
Also read: Road Trip in Tuscany
I arrived late Monday night, which is a rough day even for my favorite restaurants in Rome. There was absolutely nothing open except the little tabacchi/wine bar on the corner. It’s not the first time I’ve had potato chips for dinner.
I woke up on a Tuesday morning eager to explore Pienza. Luckily, I didn’t have to set the alarm early to get up before the hoards of tourists like I would in the summer. I walked along the main pedestrian street and only saw a handful of locals. My favorite was an old lady decked out in fur headed to the coffee shop.
After walking along the man pedestrian walkway, I circled back along Via del Casello. The views from this look out are what Tuscan dreams are made of all year long.
Luckily, the best cheese shop in town was open. Marusco e Maria (Corso il Rossellino, 19, 53026 Pienza) is the place to get pecorino, Italian spices and local wines.
Cheese and goodies in tow, I headed out to see the tiny Chapel Vitaleta on the hill. It’s a little tricky to pull over, but this location offers a nice view of the front of the chapel.
I continued to Bagno Vignoni, a small town with a thermal spring discovered in Roman times.
On the plus side, there were literally no other people around, parking was easy and hotels were inexpensive. Winter can be a wonderful time to explore the region, but expect things to be sleepy during the weekdays.
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