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Grindelwald to Venice

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We already have the Swiss Pass in hand for late December train travel within Switzerland. What is the best/quickest train route from Grindelwald to Venice (assuming we must connect through Milan)? When and where should we purchase the Italy portion of this train travel (assuming the Swiss Pass only gets me to the border station I hit along the way)? Should I purchase the Italy portion of this train trip in advance? Thanks.

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