Tuscany and Umbria - Early December

1. If you plan to take a train upon landing then pre-purchasing is risky. If you miss the train you booked because of flight delay your money is lost.
2. I don’t think it is overly crowded in December, so the lines won’t be too long.
3. If you have a car don’t stay in Perugia. Even in Assisi there are car restrictions, but it’s much smaller (and quaint) and you should be able to find accommodations with car access and/or nearby parking that are walking distance from the historical center sights. Regarding the split is up to you. However if your flight is early in the morning, you need to spend the last night in Rome or at the airport.

Cars are required to have snow tires or available chains in Tuscany and Umbria from Nov. 15 - April 15. Be sure your car rental company complies. Also you need an IDP for driving in Italy, available from the CAA.

Roberto and Mike, Thanks for the info and advice. The rental car comes with chains. Is snow common that time of the year?

https://wanderlog.com/weather/9802/12/siena-weather-in-december#:~:text=The%20average%20temperature%20in%20Siena,F%20(18%C2%B0C).

Have you considered the Caribbean? That’s where we like to go in the winter. Northern Caribbean can be cool in January, but we bring sweatshirts.

Snow is rare at any time of the year at the altitude of the locations you cited.
Montepulciano is probably the highest but I doubt it is over 600 m. above sea level.
Maybe the top of nearby Mount Amiata might get some.
In the very unlikely event it snows at lower elevations it will be just a bit that will melt quickly. Just a great opportunity for a wintry photo of the Tuscan and Umbrian landscape.

Great. Thanks for the info.