Not crazy about Milan, but Como is lovely, and Rapallo is a wonderful base for visiting Cinque Terra and Portofino.
I am not crazy about Milan either. Although the Dumo and the Last Supper are on my bucket list. It is just where the plane flys direct from Boston. It is more of a gateway to get close to the places we want to go.
Where is Rapallo in comparison to Monterossa. I ask because some friends stayed in Monterossa and hiked or tokkk the train to the other Cique Terre towns. Portofino is out of my price range to stay there.