Siena or Orvieto?

Amanda, my thoughts would be yes, yes and yes! These are three of my favorite spots in Italy, each different than the other. I do think that on a first trip to Italy, it is very important to include one or more smaller cities and towns, along with bigger and more heavily touristed, also wonderful, places like Rome, Florence, Venice and Milano. You have not shared how many days and nights you will be in Italy, or what the rest of your itinerary is, so it's hard to make any specific recommendation. Assisi and the old section of Orvieto are really small towns, with various beautiful sites, and lots of good restaurants, small shops and views. Siena is the same, only considerably larger than the other two. One thing they all share is a lot of day-trippers, so that staying at least one night allows you to enjoy the evening and early morning, often the best times of day, much less crowded. You can't really go wrong with these choices, so enjoy!

Orvieto was under water when we went so it is hard for me to judge. The one place in Italy that I wish I would have spent more time, Sienna.

I very much agree with Mary that I would have liked to have had more time in Siena. We have not visited the other towns that you are considering, but can tell you that Siena is well worth the time you give it. We planned to take a train from Rome to Venice after a Mediterranean cruise and a friend suggested to spend a night in Siena on the way. We were so glad that we took that advice and thoroughly enjoyed our time there! We walked inside the city wall, visited the piazza where the Palio is run, met some beautiful, friendly locals, sampled wonderful cuisine, and generally added to our total perspective of Italy. So yes, if you can fit a visit to a smaller town, by all means do it!

Have to agree about Siena. So this time we chose it as our base for six days. Orvieto and other towns we will day trip in.

I was in Italy a couple of months ago and stayed for two nights in Orvieto and a night in Siena. It was my first visit to Orvieto and third (sort of, previous visits even briefer) to Siena. Both are great, Siena was way more crowded in the beginning of November. I felt as if I had Orvieto nearly all to myself. I think Siena is more historically important but for me Orvieto is its equal in overall appeal. Big city Italy can be exhausting, definitely worth it to break it up with smaller cities. The trains make it incredibly easy to travel among these cities, go for it! Assisi is on my list for the future, too.

Really, all three are wonderful. Siena has LOTS of international students. Assisi gets lots of religious day-trippers. Orvieto is not as famous as those other two, but still gets a decent number of day-trippers.

I agree with the comments that if all your other stops are cities, it would be a nice change to visit a smaller town. All three you've considered are good stops. Orvieto is small, relatively quiet, and very, very old. I am interested in an earlier writer's comment that Orvieto was under water when she visited. I'm not questioning that her observation is correct, but I can't quite picture how Orvieto, perched on top of a butte, could flood. I'd welcome more details about that.

How are you traveling? If you are driving then absolutely Siena which is one of the most lovely cities in Italy and well worth a night. But Siena is not on the way to Rome if you are traveling by train. It is an easy bus trip side trip from Florence but getting from Siena to Rome by public transport is a major pain. There are a couple of hotels within the walls in Siena with parking -- Athena and Palazzo Ravizza are two we have stayed in and it is a great stop if you have a car. Otherwise do it as a side trip from Florence and do Orvieto as a sidetrip from Rome if you like.

These 3 towns are all fantastic but very different and the travel logistics are different. A day trip from Rome northeast to Orvieto is easy by train because it's not far away. A day trip from Florence southeast to Siena is easy by bus or train for the same reason. But neither of these towns is on the usual Florence to Rome train route which is a frecciarosso direct fast train. So neither would work as a stopping place along the way unless you rode regional trains and maybe changed trains enroute. But for Assisi, while it's farther away from Florence and Rome than the other two towns, it's definitely on the way going south, you just have to jog east 3 hours by train from Florence to Assisi and then jog west 2.5 hours to Rome. This would be impossible as a day stop but would make a marvelous overnight stop. To me, it's much more lively than Orvieto and much less crowded than Siena. And yes, there are many people coming to see the Basilica as pilgrims, but even for a non- believer, this church is one of the amazing artistic treasures of Italy. And the town is absolutely lovely to walk around in.

Edit: and of the two hill towns, Orvieto and Assisi, I think Assisi is more beautiful, the views of Umbrian countryside more spectacular and view from down below to the town perched at the top more glorious.

Both Orvieto and Assisi are beautiful with small hilltop historic centers and scenic vistas of the surrounding Umbrian hills. Orvieto is a shorter train ride (both from Florence and to Rome) and a better connection from the station to the "upper city." You could even consider 1 night in each, Assisi first.