itinerary opinion

Check for cheap flights to Florence, Bologna, Verona, Pisa.

From Bologna you have options for a day to Modena/Parma/Ravenna/Ferrara.
From Verona you have options for a day to Vicenza/Mantua/Padua.
From Pisa you have easy connections to stay in Lucca, or visit Cinque Terre..

How about Venezia? Or, stay in Germany and visit somewhere you can't do as a daytrip from Munich (Aachen, Koln, Trier); perhaps Berlin and fly out of there.

For only 3 days in Italy I would suggest or a 3 days in Florence and surroundings (a visit to Chianti, Montefioralle, Montaione and the area of Iano di Montaione, Castelfalfi, San Gimignano and Volterra) or just 3 days in Venice. Or 2 days in Venice and one in Verona.

In Germany, being in Munich, I would not go to Cologne or Trier, too far away.
I would rather visit Rothenburg or wurzburg or nurnberg or Salzburg (Austria) not very far away. Another nice thing to do in the area is going to the Titisee (lake).
There are many air connections between Milan and Munich (I think 7 or 8 per day)
Milan is easy because of the train connections to any part in Italy.
However, I would choose more for Venice or Florence, I know they have direct connections for both cities, choose one of them depending on your time schedule and on fares. Both cities are gorgeous. If you choose Milan try to see if you can go to La Scala for an opera and of course go to see the last supper.

I'd just rent a car and drive in a loop through Garmisch to Innsbruck--through the Tirolean mountains. You could also go to Salzburg.

If you want to go to Italy, Vueling can get you inexpensively to Rome and EasyJet can get you to Milan.

Thank you all! Will decide today....much appreciated.

If you can get a cheap and early flight I'd say Rome. If not Florence, is enjoyable but I personally found it overrated. The other thought I have from Munich is maybe somewhere in Austria or Prague? I've never been but I hear good things and I don't thing either would be very far.