I am flying in and out of Rome.
this is my itineary.
Get into Rome , train to Florence(2 nights), then to venice(3nights), to MIlan(3nights, including a day trip to Como, back to Rome. We thought of going down South to stay like in Capri, etc... or should I go to Sicily . Don't actually llike to be on the road too much, so please if you have any suggestions, tell me!
Spend less time,preferably NO time, in Milan. Use it to go to Lake Como and to take side trips to Verona and Lake Garda. On Lake Como, stay in either Varenna or Nellagio or Menaggio rather than in Como, which is vwey big-city in its feel. It is likely to be cold up north, so you perhaps your time would be better spent in Sicily
Dump Milan from that itinerary and do either Cinque Terre or one of the lakes (Como or Maggiore). And why are you going back to Rome? Go open-jaw - fly into one city in Italy and go home from a different one. Why waste all the time going back to where you've already been?