Choosing a drop off point for the car

We've dropped a car off in Venice and taken a train to Milan, so I don't have a drop-off suggestion, but if you're leaving from central Venice, consider taking the train to the Mestre station on the mainland and picking up your car there. Depending on what rental company you use, they may have various locations for collecting/returning a car that will be more convenient and/or without extra costs.

We often, when traveling to big cities, choose to drop our rental car at the airport, just because it's usually pretty straight forward and has the most extensive open hours. However, Malpensa Airport is a rather long way from Milan. Many of the car rental companies have offices at the station. Just be sure to get very precise directions for how to find the return area. We once , a long time ago, spent a long, frustrating time, trying to figure out where to return our car. Turned out there was a ramp around the back of the station, but you couldn't see the sign until you actually turned to go down it.

I haven't done this personally, but others here have posted that picking up a car in Venice at Piazzale Roma is easy. The only catch is that the causeway to the mainland has speed cameras, and if you go even a bit over the speed limit, you'll get a ticket - months later.

For Milan, I like the airport idea, but don't use Malpensa - use Linate. It's east of the city, so it's in the correct area arriving from Lake Garda, and it's much closer to the center than Malpensa.

Pick up Piazzale Roma.
Drop off near Stazione Centrale. Driving in Milan is not bad, provided you avoid peak commute.

If you have not driven in an Italian city, some N. American drivers report it is a more intense experience that they were expecting. Even more intense if you are not adequately insured.