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Help with Tuscany and/or Umbria 10 day trip!

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Please help!
I have been reading trip reports on Fodors and I am just beginning plans to Italy in mid-May for 10 nights with my husband and daughter, 24. It is a college graduation trip for her, in part. I know it is getting late!!
It has been 26 years since husband and I went to Italy. We are interested in focusing on food, wine, art, scenery, history, architecture, experiencing the culture. There is so much that we would like to see, but of course don't want to move too much.
We plan to fly in to Venice. My husband and I have been there, but our daughter really wants to see it. We will maybe spend 3 nights to recover from the trip from LA. My husband has a very bad back right now, but is determined to go. I am looking for ways to keep everyone happy. My daughter and I will want to walk much more than my husband. Town/cities that are not too small, not too big. Good restaurants, cafes, a wine tasting, maybe a cooking class., not museums so much as living art ......Driving some is fine....

Please tell me how this sounds --just forming ideas--
Venice -- 3 nights
Florence--2 or 3 nights or stay in Lucca or Sienna?? Then get a car.
Montepulciano--3 -4 nights with day trips to Ferrara (husband's wish), Chiati, maybe Raveena

I wanted to see Orvieto. Assissi, Gubbio. Not sure yet where we will fly out of.
Any advice is appreciated!! Thank you. I am working on this trip this weekend!!

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