If you aren't flying everywhere and want to spare yourself some driving, I'd really recommend a train trip through the Alps, winding up at Milan. There are a couple of "local" trains that don't just tunnel under it all, we went via Poschiavo through to Basel. There are others that go up from the Lucerne end, and I think there is a scenic special that runs across the high valleys. Book these via the Swiss rail website, easy.
There is a lot of pretty walking (and climbing) in the Swiss alpine valleys if you want a stopover in the middle. I wouldn't get over excited about Swiss food however.
You can pick up a rental car in Milan and drive up to Bolzano or Bressanone or thereabouts for a night (or possibly an extra day via Verona) then into the Dolomites. That time of year there is no ski crowd and it is very quiet, Cortina d'Ampezzo is a great place to stay. The cable car up onto Lagazuoi and the old WW1 trails is pretty cool. There are cable cars, via ferrata and routes everywhere.
From there you can easily drive down via Belluno to Venice (if that's a goal) and South. Again, if you're not keen on driving a lot, the Italian trains are pretty good from Venice.
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