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Milan to Munich via Bernina Express

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My friend & I will be vacation around Italy & our last stop will be at Italy Milan & from there we need to get to Munich around 10 Nov 2013. Is there a possibility of travelling by rail from Milan to Munich Via Bernina Express? & How munch time needed ? Do we need to stop over some where & continue the journey later? or advisable to stay some where for the night before hopping on the next train to Munich?

Or instead of our last Stop at Milan we should change to Venice?

Thanks in advance

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