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Vienna to Milan

My husband and I are celebrating our 40th anniversary this spring and want to take in Vienna and Milan. We have been to other parts of Italy (Rome, Florence, Venice)but want to explore the Milan-Como area. We enjoyed Salzburg on a previous trip, but never got to Vienna. So, the goal is to plan a trip that would fly us into Vienna where we would spend several days, take a train then to Milan area to end the trip. Questions: is it feasible to do the train, should we plan on lots of getting off and on? What are "must sees" within these perimeters? Should we take night trains or a combo, are there problems going from country to country by train? We would probably consider driving as we have on previous trips, but the drop charge can be awfully high. We will probably plan on two weeks to accomplish this. Any suggestions or advice would be greatly appreciated!

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