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.
Rapallo is a village on the train line south of Genoa and a quick train trip further south to Monterossa. From Milan Centrale you can get a direct train that takes a little over two hours. From Rapallo you can take a ferry across to Portofino for a quick visit - definitely too pricey to stay for me too, and not that convenient as the train doesn’t go to Portofino. You can stay in the center of Rapallo, right between the water and the train station, with lots of nice restaurants and beaches if you’re there in warm weather. Spent 3 weeks in Rapallo with family in September and had a great time. Took the train down to Cinque Terre one day (there is a separate train system that shuttles back and forth between the five villages) or you can hike the full stretch if you’re up to it. All the villages are easily accessible from the train stations except for Corniglia, which requires a serious hike up many flights of stairs. Also, you need to be vigilant to get into the Last Supper, as there are limited “entries” and you need to buy tickets in advance. It’s tricky as they only sell tickets online within a limited time window - so you can go online and it’s too early, but once they are available they sell out and it’s too late. My experience :(