December Itinerary - 8 nights

I’ve been to Tuscany and Rome in early Dec and didn’t have problems with the weather but that doesn’t mean you won’t. Instead of picking up a car in Rome, take a direct bus to Siena and rent a car in Siena so you don’t have to worry about the ZTL laws. Are you familiar with ITs ZTL zone laws?
I visited San Gimignano as a day trip before moving on to Volterra where I spent one night. You could do it all in a day but it would be a long one.
I’ve also been to Montalcino and Montepulciano. If I did it again, I would skip Montalcino (the town wasn’t much) and visit Pienza’s old town before continuing on to Montepulciano.
The drive from Siena to Montalcino on the Sienese Crest Road is the most scenic drive I’ve taken. There were so many landscapes of rolling hills and very well-maintained farmhouses that forces your mental walls to float away and makes you wish you lived on one of those farms. I also liked the drives to San Gimignano and Volterra (especially Volterra) but the Sienese Crest Road was the winner.
Have you been to Rome and Florence already? With nine days why not spend your time in Tuscany and Umbria where you can sleep at agriturismos?

What are your expectations in Tuscany? The scenery will not be charming - bare trees, rows black stumps in the vineyards, maybe cloudy, even rainy days. Hill towns can be pretty cold. I stayed in Greve in Chianti at the beginning of April. At 7 am, my car was covered in a thick hard layer of frost, nearly impossible to scrape off enough to drive to a sunny spot where it would melt off. At least some of the hill towns get snow, though maybe not that early. Days are short. Stay in places where you know you'll have things to do on those long evenings. Take into account what driving conditions may be like going up and down on narrow winding tjwo-lane roads without shoulders.

Thank you both for your responses. Our plan was to drive to Siena and park in one of the visitor lots and walk or take cab into town, depending on how far lots are. Would also depend on our hotel location (not yet selected). Would do same thing in Florence. Good plan or not?

Thought Agriturismo lodging might be better in high or shoulder season? For the most part, trying to stay in larger cities (Rome, Siena, Florence should fit that bill) where there will be a bit more life this time of the year. We realize the landscape will not be as beautiful in the winter but thought it would still be worthwhile to check out some smaller towns. Very excited about Montepulciano and Orvieto. Would it make sense to stay one night in each or better to do 2 in Orvieto? We usually try to do 2 night stays whenever possible.

Do you think it's necessary to reserve tickets to visit museums and other tourist sites in December?

Also, could anyone comment on thermal baths experiences in Tuscany?

Thanks again for your input.

There’s a big car lot outside of Siena’s old town so you won’t need to take a taxi. Are you familiar with ZTL zone laws in IT? I hear Florence is strict meaning there’s no room for error; do your homework to avoid costly fines.
The problem with ZTL fines is that the rate increases the longer it takes to pay it. When renting a car, it takes a while to find you and can take six months before you receive a $300 bill; spending seconds in the bus lane is costly. I sure would hate to make that mistake twice.
A lot of people feel two nights in Orvieto is what’s needed to appreciate it. If you go to Civita di Bagnoregio you many want to stay in Oriveto for three nights.
When I was in Tuscany, I spent one night in Montepulciano and a night in Volterra that made me enjoy it more had it been a day trip. Two days are good if you arrive late in the day and leave early on the day of departure.
Good day trip options from Montepulciano are Pienza’s old town and a good day trip from Volterra is San Gimignano (or vice versa).

What are your expectations in Tuscany? The scenery will not be charming - bare trees, rows black stumps in the vineyards, maybe cloudy, even rainy days. Hill towns can be pretty cold. I stayed in Greve in Chianti at the beginning of April. At 7 am, my car was covered in a thick hard layer of frost, nearly impossible to scrape off

We spent 10 days in Tuscany just before Christmas a few years ago (pre-Covid). We stayed just outside Greve at Castillo di Verrazzano. Our experiences in Tuscany was nothing like what was described above.

It was far from a barren landscape. Yes, the vineyards had been pruned, but there was plenty of Fall color remaining. All but one day was sunny. There was delightful fog some mornings, but it burned off quickly. There was one morning we had a light frost on the car, but most days the highs were in the low to mid-60s. We dressed in layers with light coats when needed and maybe a light sweater in the afternoon, if that.

It is a delightful time of year to be there, with Christmas decorations and Christmas fairs. The days are fairly short, but with good planning that's no problem. I wish I could post some of the photos we took to show you how lovely Chianti/Tuscany is that time of year.

PS Study road signage and ZTL rules. Strictly observe speed limits. Assume anywhere within the walls of a hill village is ZTL. We found ZTL areas clearly marked and had no problem avoiding them.

Thank you Doug Mac and Mary Pat. Definitely feeling a little better after reading your posts. I was really starting to question doing this trip. Not really familiar with ZTL laws in Italy. We relied on public transportation last time we were there so didn’t need to pay attention. At this point, considering skipping and adding a day in Rome. So itinerary could look like this:

3 days in Rome
2 or 3 in Siena
2 or 3 in Orvieto

Better to do 3 in Siena and 2 in Orvieto? I believe there’s more to see in Siena and that would also give us time to swing by Volterra, SG and the Chianti region.

Thanks again everyone for taking the time to share your insights.