Milan, then what?

Lake Maggiore-Stresa could be at end as it is an easy bus ride to MXP-no need to stay twice in Milan

Bologna
Bergamo
Verona
Lake Garda

We're flying in and out of LIN.

Who is we? Do they have a say? Do you like wine? Piedmont is a nice area to have a car.

I’m not a fan of Milan, so I would probably spend no more than 2 nights at the beginning or the end (a car is not recommended while staying in Milan, as it would need to stay parked in an expensive garage the whole time).
Christine suggested Stresa on Lake Maggiore, which is very close to the airport. I second the suggestion, and since there is so much to see in that area (Borromean islands, Lake Orta, Orta San Giulio, Cannobio, Locarno, Cento Valli scenic railroad, etc), I would probably spend 4 nights in Stresa.
A car for lake Maggiore and lake Orta wouldn’t be a bad idea, but it is possible to use only public transportation (buses, trains, ferries).

The list is really endless of other locations you might want to consider:
Langhe and Monferrato (wine country) of Piedmont
Val d’Aosta, Mont Blanc, and the Alps in the region
Lake Como, north of Milan
etc.

Also many interesting cities are in northern Italy besides Milan, such as:
Turin
Bergamo
Parma
Bologna
and so on.

Obviously cities, like the ones mentioned above, are best done without having a car, which would be a very expensive hindrance. So if you include cities in your itinerary, as well more rural/lake locations, try to concentrate the car rental days for rural areas and the no car days for the cities separately. For example you could start with the city of Milan, then take the train to Turin, and visit Turin for a few nights, then rent a car in Turin and head to the areas where a car is more useful (wine country, lake Maggiore and Lake Orta), and finally return the car to the Malpensa airport before flying home.

I had missed that you are flying in and out of LIN.
In that case the suggestions above for Lake Maggiore and Piedmont may or may not please your plans.
LIN is very close to Milan city center, therefore I would consider spending the Milan nights at the tail end of your trip. If returning from LIN, it makes sense to be in Milan the night before your flight home.

Upon arrival you could still consider heading out to a lake.
Lake Maggiore and Lake Garda (to the west and to the east of Milan respectively) are two options.
Lake Como to the north of Milan is another option. They can all be reached by train, although you can also rent a car and visit them by car (although I don’t find a car useful at all at Lake Como, as the important spots are more easily reached by ferry.
The Dolomites are another option (I prefer a car for that)
Verona, or the cities of Emilia Romagna could also be considered.

So many choices, not enough time.

Take a train to Assisi and enjoy the Umbrian countryside!

We've been in Umbria. We stayed two weeks in Todi and traveled about.

I don't know your interests. But for me, as I am for scenery and good food, but not for big cities, why all of them looks alike, It would choose Varenna for at least 3 or better 4 nights. From there you can visit almost every town/village around the lake by ferry or train.
But if you be for big cities without the really italien flair, then it is the wrong destination.

I am too into scenery, good food/wine. Not so much about big cities, but we do love a great art museum and beautiful cathedrals. Great classical music is a bonus. And I don't believe in moving around a lot. Get a central hub and drive around a bit.

We get in early afternoon on April 30th. Spend the rest of the day getting over jet lag. Stay in Milan until May 3 (unless that is too long?) rent a car, then go to Varenna or another recommended lake town until the 7th.

I do love and know about wine. Would the rest of our time be better spent in somewhere like Alba (for Barolo's/Barbaresco's), Verona (for Amarone's), or Parma for food?

Our flight doesn't leave until 14:00 on the 12th from LIN.

I would spent two nights in Lake Como, two in Bolzano, and 4 in the Cinque Terre. Choose between the 5 towns (I chose Vernazza) or beat the crowds by staying in nearby Levanto.

Bologna is magical. If you like food, can’t be beat. Take a Bologna Greeters walk. It is a short train ride from Milan. From there, day trips perhaps to Ravenna mosaics, toFerrara, etc. then wend your way towards airport perhaps. Iwould not want or need a Carin Ravenna or Bologna. However, do not use Uber in Bologna unless you like high charges.

We get into Milan in the early afternoon. So, I'm thinking two nights to get over jetlag and to see a bit. Then drive up to Varenna for four nights.

We do love and know good wine and food. So, I'm thinking about five nights in Alba (Barolo/Barbaresco) or Verona (Amarone) .

Parma and Bologna are an enticing alternative.

Our flight is at 14:00 on the 12th, so we can drive back to LIN in the morning.

Thoughts?

For what you intend to do I would probably choose either the Dolomites or the area around Lake Garda. If you have at least 3 or 4 nights for each I would do both. That way you can mix lake, mountains, wine (including Valpolicella or Franciacorta), and also a beautiful city like Verona, which is within easy strike from the lake. Since you plan on a car, I wouldn’t base myself in a city.. If you arrive at LIN in the afternoon, you could also consider taking the train to Verona to spend two nights, then rent the car in Verona after visiting Verona amd head to lake/mountains (and return the car to Milan before flying home).

Our last trip, we flew into Milan and took the train to Verona, then train to Venice. Verona was a find! A UNESCO heritage site, with a functioning Roman coliseum, surrounded by river on three sides, easy walking.

How did you like Milan? How long do you think would be a good stay?
I'm thinking about two nights in Milan, train to Verona for three nights, drive to Varenna for four nights, then three nights in Alba, then drive back to Milan the day of our flight.

I was in Milan in late September. I enjoyed Milan, even though I wasn't expecting much compared to rhe other cities i visited on that trip (Padua, Venice and Paris). I like art, Cathedrals and historic sights. The Duomo and it's rooftop is a must see while there. The Galleria Vittorio Emanuele II is right by the Duomo and worth seeing. Lots of great restaurants and upscale shops to visit in there. Of course, you must see the Last Supper while in town. There is also a historic castle (Sforza Castle) with a small museum that contains Da Vinci's unfinished last sculpture. Enough to fill 2 or 3 days, depending on how fast you tour them. The challenge will be getting reservations that work with your timing on visiting the Duomo and the Last Supper.

We enjoyed Milan a lot. Definitely get tickets for a tour of the Duomo, including the rooftop. Enjoyed exploring the Brera district. Unfortunately, we couldn't get tickets for the Last Supper.

We also loved Verona! Such a pretty city with lovely piazzas and easily walkable. We did a wine tour of the Valpolicella region with Pagus Tours. A highlight is the art museum at Castelvecchio. This is a wonderfully curated museum located in the castle/fortress that includes a walk along the ramparts. The Pagus Tours office is across the street from Castelvecchio.

We stayed in Varenna. You don't need a car. You can easily take the train from Milan to Varenna or from Verona to Varenna, depending on your itinerary. We enjoyed staying in Varenna and taking the ferry to see the other towns. There is a beautiful villa you can tour in Varenna, Villa Monastero. We also loved Villa Balbianello in Lenno. Menaggio was fun to visit, too, not as crowded as Varenna or Bellagio.

If you enjoy spectacular mountains and the ski resort vibe, after your arrival you can take the train from Malpensa up into Switzerland for several days before returning to the Milan area. Last Fall we took the train from Milan to Domodossola (where the Italian and Swiss trains meet - nice town with medieval center) for a night before Zermatt for four. Then we went to Andermatt for 2 nights before heading to Zurich. BTW - trains also run from Andermatt back to Milan.