Last Updated on 11/11/2022
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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Lisa says
Thanks for your article, very informative. We will be in Tuscany the first week of December. Having a hard time finding information on any events happening. Do you have any recommendations?
Scarlett | Petite Suitcase says
You can find several small Christmas markets. A few years ago, I went to one in Montepulciano and Florence. I would recommend both 🙂
Laura Dienzo says
Thanks for the info on visiting Tuscany in Winter. We plan to be there end of December into mid-January. We plan to spend a week in Florence and only use public transportation. We will have a rental car for the second half of our time in Tuscany and we are trying to decide on a good town to stay in where we can explore in our car. Do you have any recommendations for a good home base in winter with a car?
Scarlett | Petite Suitcase says
I have always been fond of Montepulciano and Siena. They are both near the freeway so easy transportation via car. I think it would also be nice to stay in a cozy villa in the countryside, but that depends on your preference.
Hannah says
Hi! Thanks so much for sharing! Am thinking of taking a road trip through Tuscany and seeing the Val d orcia in the first week of December. Do you know if it would still be scenic or would the fields just be barren
Scarlett | Petite Suitcase says
Hi Hannah, The rolling hills won’t be quite as picturesque as postcards, but it will look similar to these phots. The small Christmas markets should be going and those are very festive.
Kimberly says
Any suggestions for what to pack for a Mid February stay in Tuscany?
Scarlett | Petite Suitcase says
I would check the weather forecast for what area you will be exactly, as Tuscany can really vary by city. I remember when I went in winter, I definitely needed a light coat and the nights were chilly. I wore a scarf and boots the whole time. Hopefully, you will get lucky with some sunshine!
Rock DeAugustine says
Ty, most helpful information I found on Tuscany in Winter so far, by far.
Scarlett | Petite Suitcase says
It is not the most popular time to visit, so I can see why there might not be a whole lot of information out there about it. Glad I could help!
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!
*Hotels links are affiliate.
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!