Here's my question: Does this pass only work when both stops are in Italy? For example: we're leaving Milan and headed to Arth-Goldhau. Would the Italy Eurail pass work since we start in Italy? Or not because we're not ending in Italy? One country passes are only valid in that one country, you cannot use them to travel in neighbouring countries. While there are a handful of exceptions to this rule, that journey is not one of them. Your options are to use a global pass instead or to pay seperately for the Swiss portion of your journey. To confirm, the key variable is where the travel ends, not where it begins?
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