One Night In Milan

I am in a very similar situation, and look forward to reading what people think. Hope your trip has been great so far! I'd be curious to know where you end up as far as a hotel is concerned as well, I still have to book our one night there. Arriving from Umbria, there for an evening, and off to Malpensa by train in the morning.

When we have one night in Milano, which is usually annually, we stay at the Hotel Berna near the train station for convenience. If we have time for a good walk, we head down to the Piazza del Duomo, maybe have coffee or an aperitivo, then head back to the area near the hotel and eat at Mamma Rosa http://www.osteriamammarosa.it/. We’ve never been disappointed. We have been disappointed when trying to find a place to eat dinner around the Duomo especially in the Galleria Victoria Emanuele II.

Last time in Milan, in order to get into the Last Supper we had to book a walking tour. Our guide, actually French grad student said, "Do not, under any circumstances, eat in the Galleria Vittorio Emanuele II."

I am not understanding your rental car issues. Are you arriving by rental car and have to turn it in in the city of Milan, or will you have turned it in previously and arriving by train. If the later, you will arrive at Milano Centrale station and the previously mentioned Hotel Berna is an excellent choice. A couple of blocks away is a restaurant, Antica Osteria Cavallini, that is very good. https://www.anticaosteriacavallini.it/

A nice and quiet place is the Brera district: it is an historical district that survived WWII bombing so many old palaces and churches are still standing; there are nice restaurants and cafes where you can enjoy a more relaxed atmosphere compared to the bustling city center, and an important museum: the Brera art gallery that collects several masterpieces by different renaissance artists (and not only renaissance art).
I agree with those who say that you should avoid restaurants around the city center (in Galleria or near the Duomo): they are very expensive and they often serve gourmet food. You need to keep in mind that Milan is quite different from the classical italian city or town, people are less "traditional" and more "international".

Nothing wrong in "gourmet food", some are sick of eating always the 10 traditional dishes and are open to pay more.

Cracco and Felice are two starred restaurants in the Galleria and one must be out of his mind not to eat there because they are in the Galleria. Assuming one is ready to pay those prices, of course. They are extremely expensive, maybe too much expensive, but the food is... outstanding.

Savini has been serving food in the Galleria since 1867, 4 years before Rome became Italy's capital. It's not great and the prices are objectively too high, but it's not a place to avoid like the plague!

Thanks all, I greatly appreciate the feedback! And @dantbarnes, it sounds like we'll be following each other on the way back up to Milan to fly out!

@Sam- We were originally flying out of Rome, but did not have the proper paperwork with us to pick up our car from Malpensa. We were able to find a local car company that would work with us in Milan city center, but that involved changing our flight home from Rome to Milan and making the trek from Umbria back up north for our flight out. Lessons learned! We are going to drop our car off in the city on Sunday late afternoon and then head to a hotel. We'll take the train to Malpensa on Monday morning.

I was thinking we would maybe stay somewhere closer to getting to a train and then take a cab or walk to the Naviglie area for dinner or drinks. And do a walk by of the Duomo/Galleries at night, not necessarily to eat in the area (unless @dario it sounds like there may be some fine dining to consider!). We're OK with casual too, it may depend on the mood after driving 5 hours that day.

Is there a reason everything I read mentions taking Centrale to Malpensa and not Caldora? It looks like a shorter train ride or is it just in terms of where you want to stay and the best station near that area?