You might want a food tour rather than an historic sites tour. Check out this one for Sceptre Tours:
http://www.roadtripsforfoodies.com/2014/07/slow-food-tours-in-italy/
Elder Hostels web page has a link to this 10-day tour for $2100-2500:
http://www.goaheadtours.com/tot/food-wine-flavors-of-tuscany-umbria
buon appetito!
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