Milan Road Trip

If you want to do the Italian coast I would not drive. It is well served by train and a car will probably be a bother and an expense you will pay everyday to rent and to park and not use. I would look at the coastline from Portofino south to CT as there are many cities to explore from way too expensive to everyday livable places. The train is just about as fast as driving from Milan to coast. Heading north into the mountains is a different story, just be sure your rental company is aware you are crossing borders when you rent.

As less obvious train day trips from Milan I would suggest Verona - arty, chic very walkable city is great for a day visit. I would also through out Brescia which I think is completely overlooked by tourists. It features a whole series of interconnected great piazzas, public art, great Roman ruins. museums and a castle on top of the hill to boot.
Bergamo, Turin (Torino), Bologna (Parma and Modena) are the obvious day trips by train from Milan.

If you like fashion don't miss the Armani silos in Milan.

Have a great trip,
=Tod

Padua is about 2 1/2 hours away from Milan, by train. St. Anthony's Basilica (especially St. Anthony's tomb), the University and Scrovegni Chapel are the main attractions. Much slower pace and a lot less tourist traffic than Milan. Reservation required for the Chapel. I enjoyed my time there.

Consider driving into the Aosta Valley. You won’t be able to do much high altitude climbing in May, but there is plenty of natural and cultural activities at lower elevations. The city of Aosta makes a good base, but there are lots of other choices in the region, too.

One trip to Milan, we immediately went to Piedmont for a brief peek (stayed in Asti and Alba without a car, would be preferable with a car for sure), then we continued on to the riviera staying above Camogli.
I agree if you choose the coast, nix the car.
For Switzerland, your specific choices would dictate if a car helps or not.
I would not day trip from Milan to Bologna, etc., but stay there instead. I'd first dig into a good book on Lombardy and that other region to the north. Too many choices to not exhaustively look a bit more, good luck!

If your road trip into Switzerland is to visit a mountain town or two you can take the train directly from Malpensa to places like Zermatt and Wengen. Don't bother with a car. If you want to explore around more of Switzerland the train still works but a car provides more flexibility. I've done both. Identify the places you want to go and then decide on transportation. Same thing for the Cinque Terra/Italian Riveria. You'll want to take the train between the Cinque Terra towns - and can also visit other nearby places via train. On our trip we drove from Malpensa to Camogli and then Portofino before arriving at Monterosso. Didn't have time for Genoa but you might. Day trips I've done from Milan include Bergamo (2 - 1 car, 1 train), Varenna (train), Stresa (train), Porto Ceresio (train - from here you can easily take the bus or ferry into Switzerland), Turin (train), Domodossola (train), and Breuil-Cervinia (car). BTW - there are lots of other great options. Have fun!

Thank you Happy Traveler. Sounds like your trips are aligned with what we are thinking of doing. Can you elaborate on your trip from Malpensa to Camogli and then Portofino before arriving at Monterosso. Did you stay in Portofino or was your base Monterosso? On your day trips via train from Milan were there any that you felt were must sees? Thank you.