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.

Here's a short report from our trip.

Such an awesome week. Landed in Rome early Monday morning and took the train to Florence from the airport. Had to change trains in Rome but everything was straightforward. 63 euros per person and about 2 1/2 hours of total travel time. Arrived at Santa Maria Novella station and checked our bags at train station so we could go explore luggage free. Visited Il Duomo and spent rest of the day walking around outside. Did not climb Domo or Campanile as we had done it the last time we were in Florence. We had particularly enjoyed the view of the Dome from the Campanile. Checked into Hotel Ariele for 3 nights and loved it. About 10-15 minute walk from main attractions. Clean rooms, quiet area and delicious breakfast. Great value! Had dinner a few minutes away at Casa Ciabattini. Wow! Food and service were excellent. Would highly recommend. It was so good we went back on our last night. Speaking of restaurants we also really enjoyed the sandwiches at All'Antico Vinaio. Everything was so fresh. Not too far from Uffizi. On our second day we checked out the Galileo museum in the morning. Spent a couple hours there. Viewed such an interesting array of equipment which helped propel human knowledge in the middle ages. Super interesting. Went to the Accademia in the afternoon. Absolutely no wait. On our last day we got the Uffizi-Palazzo Pitti combo ticket. Spent the morning at the Uffizi and checked out the palace after lunch. Impressive art collections at both. Palace offered a much more relaxing atmosphere as there were very few people there. The following morning we picked up our car at Hertz near the train station and headed towards Siena. Walked around town, climbed the tower and visited the Duomo. Awesome day and beautiful sunny weather. Drove on to Montepulciano late afternoon where we would sleep the next 2 nights. Next day we did Rick's Heart of Tuscany drive. Wow!! Incredible scenery despite the cloudy weather. Had a wonderful lunch at Antica Trattoria Toscana al Vecchio Forno in San Quirico d'Orcia. Pienza and Monticchiello were our favorite stops that day. We loved walking around Montepulciano and enjoyed the Christmas Market in the main square. Next stop was Assisi. Main pedestrian street and church (amazing art) were very crowded but we still loved it, especially when we explored the side streets which were all beautiful and peaceful. Drove on to Orvieto where we spent the next 2 nights. Another beautiful hill town. Church facade is possibly the most impressive we've seen. Went back to see it a few times while we were there. On our last full day we checked out Civita (about 30 minutes away). If you are anywhere in the area, Civita is a must. Never seen anything like it. Drove to Rome Airport the next morning. Took about 1:45. Good signage for car returns and a lot easier than I expected. Great trip. If part of your travel M.O. is to avoid crowds I would definitely recommend checking out Tuscany this time of the year.

Nice report. Glad your research and planning were well rewarded.