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.
There were two places on my list for lunch, but both were only open on the weekend. I’m hoping to try out Dopolavoro La Foce and Osteria La Porta in the future.
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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Barbare Tsilosani says
Hello where would you reccomend staying in case it snows? We will be in Chianti area for November 26 dinner in panzana. Should we stay in panzano for easy access? 27th we drive to Florence and stay there for one night
Scarlett | Petite Suitcase says
Hello Barbare,
I don’t think it usually gets cold enough to snow in November. I was in Tuscany around the same time a few years back and it was quite mild.
If you don’t want to drive up to Florence that night after dinner, you could stay in that town itself or drive about 15 minutes to Borgo del Cabreo or Villa Bordoni “. I haven’t stayed in that area, but have those saved as nice hotels. They might be closed for the season though. Terre di Baccio looks like it might still be open in November.
Good luck and have a nice trip!
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Josée Moreau says
Hello, could you tell me which month in winter you visited Tuscany? We are planning to visit late October and beginning of November.
I enjoy your posts and find they are quite helpful in the preparation of our trip. Best regards, Josee Moreau
Scarlett | Petite Suitcase says
Hi Josee,
The photos in this post were taken in late January. I think October/November is a much better time to visit Tuscany. I’ve also been in late November when the Christmas markets start opening. Most hotels are still open, the weather isn’t too terrible and there are less crowds. I believe there are even some wine events/festivals around that time. Glad you find my blog helpful!