Buongiorno,
I live near Greve in Chianti - and as charming as the town is, I have to admit that in the winter, especially in the evenings, the town is very, very, very quiet.In particular many restaurants are closd and even bars and cafes. Perhaps Montalcino would have a little more activity about it. If you haven’t been in this area before it would also provide many opportunities for new days trips exploring many hidden corners of Tuscany
(this article provides a suggested itinerary
https://www.discovertuscany.com/what...ny/cetona.html)
Even the thermal water pools (
https://www.discovertuscany.com/vald...n-filippo.html) are fun in the cooler months!
Buon Viaggio,
Donna Denise
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