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Travel to Austria and Czech republic

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My family want to to go to Austria and Czech republic but not with a organized tour.
What we want is to fly from Toronto to Prague, Czech republic go around move on via train/bus to the next country (Vienna & Rome) until we're done the countries mentioned and fly back.

Which is the best way to visit these countries via train or bus?
Is possible to do this in 2 weeks?
how much money am I looking at?
plan to make the trip by last week of May up to first or second week of June..

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