Arezzo or Pienza in early December.

Hello! Have you considered Montepulciano, just a short distance from Pienza? We were there last year during December and they have an amazing Christmas Market. The entire town is decorated for Christmas – it looks like something out of a fairytale. There are carolers, bonfires, ice skating, and even the fortress is turned into Santa’s Castle.

Most of the town is lively and the restaurants (which are amazing!) are all open. We were hoping to go back this December, but it looks like we will need to wait until next year…sadly.

If you think you will go to Montepulciano, please let me know and we would be happy to share or restaurant and B&B suggestions.

Thank you so much for the reply! I have considered it actually (as I have considered most of Tuscany haha). I really appreciate the suggestion and would love to hear more about your recommendations. Did you get a lot of rain that time of year?

I'd actually love to hear your full itinerary if you don't mind sharing!

In winter my choice would be for a bigger town. The bigger, the better.
Therefore this is what my personal priority list for a winter vacation in Tuscany would be (from best to worst)
1. A big city like Florence
2. A smaller city like Arezzo or Siena or Pistoia.
3. A smaller town but with some life like Cortona, Assisi (Umbria), Montepulciano, Pienza, etc.
4. A tiny village like Monticchiello (or many others like it), likely totally dead in winter
5. A secluded farmhouse in the middle of nowhere.

Anytime! We know the difficult decision it is to choose where to go. We actually have been going to Montepulciano for a couple of years now because we fell in love with it and its convenient location.

I think we maybe had a day or two with a little rain, but mostly remember having great weather. It’s cool in the morning and evenings and the days can get warm with the sun. I think it was mostly in the upper 50s, but we did have a day or two in the 60s. The nights get down to the low 40s.

When we stayed last December, we stayed in Charming Homes (charminghomemontepulciano.com) in a nice apartment. However, we were back this past summer and stayed at Fonte Martino (fontemartino.com) and this is now our go to. The apartment was great, but Fonte Martino is a fantastic new B&B at the base of town. The owners are great (and from the US) and we are planning to go back again next summer and then again next December for the Christmas Market.

As for our full itinerary, I had to look back at my google maps to remember where we went. We were there for the first two weeks of December and took day trips to Siena, Cortona, Arezzo, Assisi, and Florence. We also took a bunch of shorter trips to close by hilltop towns – Pienza, Montalcino, Montefollonico, and Monticchiello. We like to explore and would mostly jump in the car and go somewhere.

Hope this helps. Let me know if you need more info.

I'm with Robert on this one. And I would pick Arezzo.

Thanks all for the valuable feedback. I have spent a good bit of time in Tuscany but have not been to Arezzo or Pienza so thought it would be a bit of a new place for me. I do love Florence and Siena but have spent a fair amount of time there in the past. Arezzo might be preferable this time of year given that it is larger and would have more things open. Thanks!

Good choice. Arezzo also is well served by public transportation (rail and bus) so you can easily visit Cortona, Anghiari, Poppi, Lucignano, Castiglion F. and other towns in the Province.
You could also visit Pienza (about 1hr away) but a car would be advised for that day trip.