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Central European train travel

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my wife and I are landing in Hamburg in early May. We want to train over as far east as Cracow Poland stopping at Prague along the way. we want to head south from Cracow down to Budapest and then over east to Vienna. my question is. Is this possible to do within 2 weeks? are there any more small towns worth going to? Are there añy really scenic byways to travel on? Is that too much time on the train because I do like traveling, and looking at the sites pass by. should we stay in the old town of the city and are there any other cities along the way that we should go to.
also, I want to dress appropriately and not look like the standard American tourist. There any hints on style you can give me?

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