Stops along the way in Umbria and Tuscany

We stopped in Deruta and visited some pottery factories. (Do some research on the area-not all Deruta pottery is created equal. We, however, are happy with what we picked up there) Between Assisi and Orvieto, we enjoyed Cortona. It was an interesting hill town to walk through and didn't take long. As to your time in Siena, I am a fan of the Chianti hill area. You can catch a bus in Siena that will take you through the area and get off and visit different villages along the way. We stayed in Greve and really enjoyed it.

Very near to Orvieto is a place called Civita di Bagnoregio that is so memorable to me and my family.please check it out and see if you would be interested.
on the way to Assisi we have been to Todi which is tiny but lovely and Spoleto which we visited briefly and wished we had more time there.
Do you know that in Assisi you must leave your car in designated lots? We stayed at Hotel Umbra and a porter helped us bring our bags with a kind of reverse wheelbarrow. Not exactly on your way but from Assisi-- we were there for 3 nights-- we went to Gubbio and loved it.
Do not know if you have time but one of my favorite things we did in Assisi was to vist the Eremo delle Carceri. It is on the outskirts of the town, secluded in the woods where St Francis lived in a cave for a time.There is a self guided tour through beautiful , peaceful woods where we came upon groups of pilgrims singing. You could hear them before you could see them.It was an extremely moving experience. There is also an old monastary to discover. You can google it and see for yourself.
This is one of my favorite memories of Italy and I have been there 7 times i think.

Assisi is a two hour drive from Orvieto. There is so much to do and see in Assisi that if you are only spending one night, and leaving the next morning for Siena it won't leave you much time in Assisi if you stop along the way. Between Assisi and Siena, I agree that Cortona would make an interesting stop and not too much out of the way.

I agree that Assisi is a great overnight.If you arrive in the afternoon it will be crowded but by late afternoon the daytrippers leave and it is delightful.The next morning it is again be good until the daytrippers arrive and then you leave.

Thank you!!

Hi Paula,
I too would recommend seeing Civita di Bagnoregio while you are in the Orvieto area - very unique and memorable!
During our travels from Assisi to Siena we stopped in Cortona along the way to Siena and we thoroughly enjoyed our few hours there. Cortona is where "Under the Tuscan Sun" was filmed and it too has lots of character.
Have a wonderful trip! Candace