We are wondering about the feasibility of flying into Milan, renting a car and making a loop up through the Swiss Alps and then back to Milan (with some Italian stops along the way). We have 10ish days to play with. Does this make sense?
Be sure to buy a Swiss vignette for the car and attach it to the windshield. They cost 40 CHF and you can buy at the border or at gas stations near the border.
It adds quite a bit to the rental cost to drop off in a different country. I had looked at flying into Zurich, renting the car there and dropping it off in Italy. Price was almost 5x higher to drop off across the border....