Orvieto vs Assisi

Are you Roman Catholic? If yes, then Assisi might be an important place to visit.
Orvieto is charming.
However, Assisi has more to see. Both are good choices.

You say "whirlwind" but how many nights will you have in Italy?

Milan is droppable, IMO, and Assisi is lovely in December when the Christmas lights and decorations are up. St. Francis devised the first Nativity scene, BTW. But do not go there for less than 2 nights.

Both of those places are lovely. I'm not religious (and not Catholic), and I wouldn't say Assisi has more to see than Orvieto, just different. The cathedral in Orvieto is a pretty big deal itself and there are at least two nice museums, plus walking tours.

The Orvieto historic area may be a bit more compact that Assisi's, but I'm not positive about that. You can take a look at train schedules to see how much extra time it will take to include either of those towns in your itinerary. I'm a bit concerned about your use of the word, "whirlwind". That's not my preferred method of travel, and I wouldn't want to cut Venice, Rome or Florence short in order to squeeze in Assisi or Orvieto. Italy has dozens of additional places worthy of a visit. You can include Assisi and Orvieto next time.

I would pick Assisi. The winter weather is not bad in Italy compared to the Midwest. You can cut Milan.

Thank you all for your input!
I had been thinking about cutting Milan and now after hearing from a few people that out of all the places we have planned it would be the one to cut, I think we will do that in favor of being able to slow down a little in all the other places. We'll stop there next time!

We will be in Italy for a total of 10 nights/11 days and will be traveling from France so we don't have to worry about being jet-lagged the first few days or long travel times to get to and from home. I'm thinking now after reading everyone's replies that with the shortness of our trip it may be most practical to fly into Venice, stop in Florence/maybe Pisa, and then on to Rome.

...being able to slow down a little...most practical to fly into Venice, stop in Florence/maybe Pisa, and then on to Rome.

Agree 100%. With the stress associated with most weddings, you'll want (and probably need) to unwind take things at a more relaxed pace.

Love long and prosper.

I think that's an excellent decision, and it's great that you will be past the jetlagged phase by the time you get to Italy.

I would choose Orvieto over Assisi for two reasons. First, it's better connected by train. Second, I saw Assisi in spring when it was dry and sunny. I suspect that if you have a cloudy - or worse, a rainy - day, it will not be a gem. I also thought that Orvieto had more and better restaurant choices.

We loved Assissi and didn’t want to leave (3 nights there). In fact, Assisi was our favorite town of all in Umbria/Tuscany. Super charming, beautiful, wonderful town. Lots of great restaurants.
Orvieto was very underwhelming for us, we were not charmed or impressed and we were happy to leave.

For 10 nights, I would stick to your Venice-Florence-Rome plan. Instead of, or in addition to, go to Lucca along with Pisa, from Florence.
Add Orvieto as a day trip, about an hour from Rome via train. Too much traveling between cities can eat up your time--checking in and out of hotels, getting to and from train stations, etc.
It's your honeymoon, you will want some time to just relax!

For 10 nights I would be doing two places; if doing 3 aready I definitely would not add in another. It takes two nights to get a full day in a place and Florence and Rome are incredibly dense with artistic sites to visit -- A week is not amiss in either.

If you are flying into and out of Rome then I would immediately train to your furthest destination and end in Rome so you don't waste the second to last day with logistical travel. If you want to jam 3 places into this time, I would do two nights in Venice, 4 in Florence and 4 in Rome.

I wouldn't bother with two nights in Venice on this trip. It's not enough time there, and those nights would be very useful elsewhere.

I think the advice about how many stops to make is good to listen to. But be careful about advice regarding choosing one place over another. Be sure to try to understand why the person is choosing one over another. If it is personal feeling it won't necessarily help you. I spent one day in Milan on my 19 day trip and wouldn't choose to give it up. I loved Orvieto and did not like Assisi. I liked Milan because there were a lot of things I wanted to see there (The Last Supper, Sforza Castle, Duomo) plus other worth while things to see. I loved the Orvieto Cathedral, the fresh food market, walking through the streets. I don't know why Assisi didn't ring any bells, it just didn't.
Good luck planning your trip and have a fantastic time.

Hi, thought I would submit my two cents. I have been to both and they are both worth visiting, but I would visit Orvieto for your trip if nothing else but for convenience since it’s in between Rome and Florence. You won’t regret at least a night in Orvieto, it’s charming. I have been a couple of times in different seasons, September and February, and believe it or not, we enjoyed February better, it is NOT the least bit crowded in the “off” season. When we were there it snowed and we were the only ones walking around and we had the beautiful duomo all to ourselves, not to mention, we got special attention in the shops and restaurants. It was magical! In September it was still lovely, but many more tourists. Maybe you would like it busier, but going in December should be quieter. Just make sure to spend the night, as there can be “day trippers” and tours arriving late morning and early afternoon. I’m not sure the order of cities you’re visiting, but we went by train to Orvieto from Rome, then to Siena (another favorite worth a visit) and Florence. It’s an easy, short, and convenient route. Ciao! Hope you have a great trip and happy wedding!

I skipped Assisi due to time restraints and did a day trip from Rome to Orvieto. I though it was absolutely charming and the Duomo is fantastic. Food was pretty good too. In fact, we spent our wedding anniversary in Orvieto and it was a perfect ending to our trip. Train ride is quick and the funicular ride is fun (views are lovely from the town). It's a great place to wander. Our only hiccup was a 3hr train delay at Termini in Rome. Enjoy!

Orvieto was nice, but I loved Assisi. It was a very emotional experience for me, much to my surprise. But as others often say, no matter where you go, you'll love it!

Have fun and enjoy your trip!