Munich to Milan

In Munich we are interested in spending the majority of the time in the city and getting a good feel for it. I have been there before but noone else in the family has. While in the city, we would like to meander and go to some of the museums and parks. Then we are hoping to take a day trip out of the city, particularly if we rent a car, and see a bit of the Bavarian countryside as we make our way to Milan and would like information on what the best route to take would be. I understand the World Expo is happening in Milan this summer and so we are a bit worried about finding accommodations in the city.

The World Expo in Milan has been discussed here, and the thinking here is that it will have an effect on the availability and perhaps price of lodging in Milan, even though the effect will be stretched over a several months long period. And also an effect on crowds, lines, etc.

The eastern part of Switzerland, though expensive, is on your way to Milan from Munich.

In Bavaria, popular sights are Neuschwanstein, Fussen, and Reutte, those are to the southwest of Munich.
German trains are good.
And many travelers find that driving in the German countryside is easier than in some other European countries, more like driving here. And you can get on the Autobahn and let your Inner Race Car Driver come out.
Probably best to try to avoid driving in German cities.
To the southeast are Salzburg (easy to get to by train), and also Berchtesgaden for some WW2 historic sights.

How much time do you plan in Munich and are you trying to see more of Germany, or mountains, or Italy? You have many options, including side trips near Munich; crossing Austria and stopping in the Dolomites (such as Bolzano and Castelrotto) and in Verona; crossing Switzerland and stopping in Pontresino or St. Moritz, then continuing south via Varenna on Lake Como; or heading straight to other Italian destinations like Venice or Florence, before Milan.

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Keep in mind that if you rent a car in Munich and return in Milan, you'll likely be facing HUGE drop-off fees. I believe you'll have to buy tax vignettes if you travel into Austria or Switzerland (HUGE fines if you're caught without them). The fines in Austria can vary between €300-3000! In addition to that, EACH driver will require the compulsory International Driver's Permit for driving in Italy, and there will also be CDW, high fuel costs, highway tolls, parking, etc.

Travel by train would be a much simpler option.

There are EuroCity trains (EC) from Munich to Verona every two hours during the day (five of them). With advance purchase from the Bahn, you can get really good fares for the Munich to Verona leg (11 year old goes free), then get a fast train from Verona to Milan with an Italian ticket.

You could also go from Munich to Lindau, then through Switzerland (Gotthard line) to Milan.

All excellent suggestions. Thank you. Does anyone have any suggestions of someplace to stay in Milan with two adults and two children?

For places to stay, are you considering a hotel or an apartment? If a hotel, what price range? You could stay either in the area around Milano Centrale as that provides easy access to transportation, or you could stay closer to Via Dante and the Duomo as it's easier to walk to the main sights. Via Dante also provides good access to the Metro and to MXP via the Malpensa Express from Cadorna station.

If you have access to the Italy guidebook, there are lots of good accommodation suggestions there.

Thank you. Yes we are trying to decide about whether to look at hotels or apartments. We're a family of four so I'm not sure family rooms in hotels will accommodate us. We would ideally like to spend about $250/night.