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Venice to Bernini Express

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Yes, sounds convoluted, but we have to fly in/out of Zurich, and on last leg of 2 week trip we'd like to take the Bernini Express and ultimately end up in Lucerne - then train to Zurich airport.
It's clear that we take train from Venice to Milan, then Milan to Tirano - that's 6-8 hours depending on connections. We thought we'd stay over in Tirano (as there's really no other choice) then catch the Bernini - Chur next day and then on to Lucerne. Is this the best way? Any suggestions on a nice place to stay in Tirano, and what's the town like?

Our travel agent is suggesting going to Lucerne and doing the William Tell Express as a day trip? Is this a disappointing compromise?

Rational suggestions appreciated if it sounds like our Bernini plan is unrealistic. Thank you.

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