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Need Help with Itinerary PLEASE

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This will be my 2nd trip to Italy (been to Venice, Rome, Florence and south)
Can you check this itinerary:
Fly to and from Milan
1 night Milan
2 nights Dolmites (Bolzano, Verona or Castelrotto?)
3 nights Bologna ( day trips to Parma, Ravenna, Ferrara.?)
1 night Siena
1 night Assisi
3 nights in Cinque Terra
2 nights Torino
4 nights Lakes- Como, Maggiore
Leave Milan
I will like to use trains as much as possible;
I also like wines, any suggestions for any of these areas?
Should I change days spent and/or sequence of towns?

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