Number of Days in Assisi to really see it, vs. Siena

I only stayed one night in Siena, and wished I had stayed longer. I personally do not recommend taking any time away from it.

My upcoming trip in October is going to include 2 nights in Assisi, so I hope that will be enough time!

In counterpoint to Angela, I actually liked Assisi better than Siena. You will need a day for Assisi itself and I think then a day for the Eremo and countryside. To me, Siena is a one day town that makes a good base for traveling elsewhere. Are you planning any day trips out of Siena?

HI - we're staying outside of Siena in an old villa, scheduled so far for Tuesday through Friday, with Friday a day tour of the Chianti area with Tours by Roberto. That leaves Tuesday afternoon through Thursday for Siena and time to relax in the villa's gardens. Assisi/Siena is the middle of our trip - we start with 4 days in Rome, and end with 5 days in Florence. We booked another tour with Roberto from Florence to the Montagnola area. We're taking public transportation throughout the trip.

I also like Assisi better than Siena. I would say that 3 days would be a good amount of time to see it all and even visit the church at the bottom of the hill. (by bus)
I enjoyed just walking around and the hike to the fortress at the top of the hill.
Assisi is a lovely little town.

If you like a place that has a spiritual, contemplative feel, that is historic and has beautiful scenery, Assisi can keep you going for days. It's wonderful in the early morning when the town comes alive; and it's magic in the late afternoon and evening after the day-trippers are gone. We spent five days in Assisi last September, and would go back tomorrow if we could. The whole time was spent in Assisi proper, except for only one half-day bus trip down the hill to Santa Maria degli Angeli.

Photos here.

Another vote for Assisi. I've been three times, and stayed longer each visit. On my last trip, I spent more than a week, and never got bored. The Eremo will take you much of the day, particularly if you walk. It's my favorite place. So quiet, and so beautiful. I would also spend a few hours going to San Damiano, which is really lovely and also quiet. And I'd really suggest a few hours to just wander the town's small walkways.

I've also been Siena, and spent 3 days. I enjoyed my time there, but I feel no need to go back. However, I am certain I will go back to Assisi many times.

I love them both and go back to both as often as I can. I would say spend an extra night in Assisi. Your overnight in Siena can be magical as well, after the daytrippers are gone. I love going to the Campo early in the morning and having a capuccino as the piazza comes alive, and walking through the old, arched streets in the evening.

Both cities are big daytrip destinations, so time spent there overnight is well spent

Ok, you are all making me question the itinerary I worked so hard on! My current plan is 1 night Rome (because that is where I fly into), 4 nights Sorrento, 1 night Naples, 3 nights Orvieto, 2 nights Assisi, 3 nights Florence, and 2 nights Milan.

Should I add more time to Assisi, and where from? I could easily take out the night in Naples. Is 3 nights in Orvieto too much? Should I subtract a day from Florence (I've been before)?

Oh my! You've given me more to consider. Instead a taking a day from Siena, I may leave Rome late Saturday afternoon instead of Sunday afternoon, and spend Sunday and Monday in Assisi. If the b&b has room, this would allow time to enjoy its location in the country as well.
Thanks for all your advice. There's just not enough time to see it all. BTW - it's an anniversary trip for us, and my husband's first time in Italy. He will be blown away by the beauty!
Cam