Need help choosing areas to cover for a scenic road trip from Northern Italy

With only twelve days, stick to Northern Italy.
The Dolomites are stunning. Stay in Ortisei. Lake Garda is south of the Dolomites, then visit Verona and Bologna..
Tuscany is large with many scenic areas. Consider the Chianti region, choose a small town such as Panzano, or Radda. Or head SE to Pienza. Drive back to MXP for your flight. Lake Maggiore is near MXP so may consider adding it too.

Suki is right: stick with Northern Italy and Tuscany at the furthest. Switzerland will blow the budget and the Amalfi Coast is a long drive south. Four nights in Ortisei would be a lovely first visit. You will probably be planning a longer stay there before you even leave town. Take a couple of scenic lifts and some easy walks. You can drive the Great Dolomites Road from there. Then spend the rest of your time (which is only about a week) in Tuscany visiting hill towns and maybe drive the Chianti wine road, go to the coast of the Maremma region for a little uncrowded beach scene.

You may want to spend the first night in Milan before hitting the road after a long flight and you will probably need to spend your last night in Milan as well, so that shortens the nights available on your road trip,

Thanks Lurel and Suki.

So just to give some perspective, in the past, we have covered Canadian rockies (starting and ending at Vancouver) covering Vancouver (1 night), Kamloops (1 night), Jasper (2 nights) , Banff (2 nights), Takakkaw Falls / Golden (1 night), Kewlona (2 nights), Vancouver (1 night).... That's about 1200 miles over 9 days. Considering this speed, would you still recommend the same itinerary?

Sorry, not our style We just do not do road trips like that. Would only do it to get from point A to Point B in the US like Portland to Chicago as fast as possible, not for “vacation” or enjoyable time. I sure would not in Europe as we like being places not moving between them

Yeah. I would rather ignore your suggestions then Laurel. Yours is not “our” style either.

I'm from Calgary, so I know every stop on your previous trip well. The difference between that trip and your Northern Italy trip is the distances are not nearly so great and the sights are closer together. It will not be necessary to drive 1200 miles to fill up your days on this trip. You could (and I would) stay more nights in one place and strike out in different directions on road trips every day. You could have the same sense of accomplishment about having done and seen a lot without covering the same distance. For example, on a 10-day trip to Veneto, we went to Venice twice, Padova, Treviso, Verona, Bassano, Portogruaro and a few other places without changing lodging and saw something different every day. And missed half of what I wanted to see. Less driving, more hiking and sightseeing, but no less coverage of things seen. In Western Canada, that is just not possible - there are looooong stretches of nothing but scenery.

So, I would also recommend sticking to Northern Italy because I can't imagine running out of things to do. You could throw in extra lakes: Maggiore, Iseo, Orta, Como, Garda; extra hikes in the Dolomites; extra towns (Bergamo, Trieste); etc. You will be on the go dawn to dusk but not sitting behind a wheel.

If you must put another country notch in your belt, you can easily get to Switzerland from Lake Maggiore. Just don't stay too long, that will be your financial splurge for sure.