I went down to Switzerland, Austria and Italy to busk one February just after Carnival had ended in Köln. I stayed in Como for a couple of days and it was smashing. It's a lovely old Italian city, built around a lake. There are lots of lovely old buildings, those narrow Italian street, the cafe culture and all the stuff you expect in Italy. I spoke fifty words of appalling Italian, smiled a lot and waved my hands about and the people were friendly and cheerful. It was the birthplace of Alessandro Volta, so they have a big statue of him up there. There are plenty of better read Mudcatters than me, but it may also have been the city, from which the hero crossed into Switzerland at the end of Hemingway's "Farewell to Arms". The lake and the city bordering Switzerland both fit.
It was not too crowded at all. I would go and have a look. Milan is a lovely city too. The Piazza del Duomo is something you should not miss. In fact, if you go in Spring or Autumn, you should have lovely weather and really enjoy yourself. Happy trails!