Roadtrip Itinerary from Milan to Venice

A quick look at a map shows there is lots worth exploring on the way.

If you are foodies you might enjoy Parma, Modena, and bologna! but that is cities not countryside.

A very scenic option would be to take the autostrada north and east past Piacenza to Brescia, then drive up the west side of lake Garda with an overnight at Riva or Limone. Next day continue north to Trento ( lots of pretty vineyards) and then highway 47 ( not the autostrada) south to Bassano del Grappa for the second night. It is an easy drive to Venice from there. Or spend both nights along the lake---it is very nice.

You can return your rental car either at the airport or at Piazzale Roma in Venice. That is much easier for getting to your hotel but some companies charge extra for a drop there. However, that fee is offset by the cost of getting two people from the airport into Venice. If do that, be careful of the speed limit when you drive across the bridge. There are three speed cameras on the bridge and people have reported getting tickets from all three on one trip!

Thank you so much for the recommendations. The route you recommended is fantastic and just what I was looking for. I went ahead and changed our flights to arrive in Milan (Bergamo) rather than Genova so we can have more time traveling thru Limone, Trento, and Bassano del Grappa. We are planning on staying in Limone the first night and making our way to Trento and the winearies the following day (for my birthday).

Is there any specific winery/retaurant you recommed around Trento? Bike tours? Wine tours?
What about hotels, B&B? (reasonably priced)

Thank you for the tips. I am planning on paying the extra money to drop off our rental car in venice and will make sure to watch the speed limit closely on the bridge.

We stayed in Malcescine which is directly across the lake from Limone. You could ferry over there ( 15 minutes) and explore the old town and little ruined castle, and even ride the gondola up Monte Baldo if you like. I am recommending Limone because you will be on that side of the lake and I have heard good things. Lemon groves---what is not to like? I know that Roberto! an Italian who often posts here! recommends Limone.

I don't know of specific wineries around Trento, sorry. But you could post a separate question on that.

And then instead of staying in Bassano del Grappa, turn east on a smaller road and head for Asolo. Google pix of it---it is a medieval hill town. When we drove past on our way to Venice I wished we had stopped there ( although Bassano is very nice too). Asolo is nicknamed the Pearl of the Veneto and their tourist info online says it appeals in particular to people who enjoy meandering the back roads! wine tasting! and cycling. So you should be able to find something!

You definitely have to detour away from the main autoroute, which is not particularly scenic, comes with tolls, and follows the same path as the direct, fast train. When driving the smaller roads, it's nice to have a more detailed regional road map (sold online or in gas stations when you get there) instead of the smaller-scale all-of-Italy map. www.viamichelin.com can also help with routing, after you've identified a couple of intermediate stops.