Siena or Orvieto in November?

Florence and Rome are cities. So I'd go with Orvieto because its a hilltown. In fact, you could see a couple of hilltowns if you're willing to start early each day. For example, leave Rome and go to Orvieto, about a 1:30 ride. Breakfast in Orvieto, take the train to Assisi and bus up from station to hilltown, return to Orvieto in late afternoon. 2nd day more Orvieto in AM, then go to Cortona. Again leave bags at station, then on to Florence that nite. There are several other hilltowns that are just a bus ride up from the train station, these are just 2 examples of what you could do.

Siena is much larger than Orvieto with more sights, but Orvieto is a great smaller hill town. Of the 2 towns, I suspect Siena would offer more to do in November. From Rome, you can take a regional train to either Orvieto (about 1 hr) or Siena (about 2.5 to 3 hours, requiring a change in Chiusi). It's about another hour to Florence from either - train from Orvieto, bus from Siena. You could do Orvieto in one night, but I'd suggest 2 nights for Siena. Might be best to base "better" on whether you want to spend 1 or 2 nights in Rome before moving on. There just isn't a wrong choice to be made here. Both towns are great.

I love Orvieto. You can easily "do" it in a day. It is a much quieter town than Siena.

FWIW, one difference between the two is that Siena has a much larger contingent of students in their 20s. Also, Siena is many people's favorite hilltop town. We loved it.

I loved Orvieto when we stopped there on our Venice, Florence, Rome trip last spring. I know, it's not listed on the itinerary, but we made a lunch stop there. However, I think it would be VERY quiet in November. While I liked it much better than Siena, Siena would be livelier in the wintertime. And you can get to other towns from Siena. I would, therefore, reluctantly vote for Siena. As for bouncing to town to town from Siena, remember that you will have just finished a hectic tour of Florence and be on your way to Rome. Both Florence and Rome are busy, big towns. You might want to regroup in Siena and relax a bit, rather than dash out and try to see every hilltop town in the region.

Deb

Orvieto was one of our favorite surprises. We picked it because we were driving to Rome next and it was conveniently located. The town sits on cliffs rather than a hill like other towns, it has a major Cathedral (build due to Corpus Christi miracle), and underground tunnels that date back to the Etruscans.

We liked Siena too, it's a nice place to wander.

We were just in both towns this past November while travelling between Florence and Rome. Orvieto was very quiet; museums were closed but the funicular was running every 15 min. One thing we enjoyed in both towns was climbing the towers to see the towns and the Tuscan countryside. Still nice color in late Nov. Assisi would be nice to add depending on transport etc. I agree that you can "do" either town in a day or less.