After a lot of tweaking-- and tons of great advice from people here-- I think we have a one month itinerary. We'll see many major sites, enjoy a lot of unstructured time in the middle-- and get a chance to get off the beaten path as well.
Any feedback is welcome. And thanks again to everyone here for sharing your experience.
Milan -- 3 nights (We get in 3PM Sunday. Our 2nd day there is a Monday-- many things closed)
Cinque Terre -- 4 nights (Maybe 3 nights....not sure. Very beginning of the season. Not much to do here if raining, right?)
Lucca-- 3 nights (I'm a tenor and love Puccini)
Florence-- 4 nights (Three full days for museums, etc.)
Tuscany-- 4 nights (Agriturismo near Sienna or Pienza + day trips)
Orvieto-- 2 nights (Civita as day trip)
Assisi or Perugia-- 3 nights (Want to see Perugia and experience Easter in Assisi)
Adriatic Coast Loop-- 3 nights (Over to Pescara up to Ancona, Rimini or Ravenna)
Fermignano-- 4 nights (Fun experience-- and bragging rights. Everyone goes to Florence ;-)
Venice-- 4 nights (We'll probably drop car in Urbino and take the train up)
Fly from Venice to Barcelona on May 2,