How to use 2 passes between countries?

You might as well make the seat reservation from the point where you board the train that is continuing to Italy. If you've chosen the departure with one connection at Zurich, then reserve from Zurich to Milan. You can do that at any Swiss train station. US agents like Rail Europe would have to ship it to you; it would not be an e-ticket.

You will be using a day of each pass. When you get to Switzerland stop in at any station and tell them what you need. They will arrange your journey all the way to Milano.

Please report back after your trip and let us know how using the various passes worked for you. If your trip is still the one you originally spoke about that will be quite an adventure...

Happy travels.....

Yeah, hard to see how you're making a killing by using two days on two passes for a single journey. It's important to read Rick's (our host here ... ) free pages on rail travel in Europe before buying either passes or point to point tickets. I will say that if you miss the deadlines for discounted point to point, passes can start to look better.

Also, although the Swiss Travel Passes now come pre-validated, the Italian pass needs to be activated by a Swiss train station agent to start the one-month travel window (such as June 15 - July 14).

As Tim mentions, we wouldn't often recommend two different passes on one trip. Switzerland is sometimes an exception with the expanded coverage of that single-country pass, plus the fact that there is no 2-country pass option for Switzerland and Italy. (And I recall that we recommended the Italian pass due to your longer train trips there and preference for a flexible schedule.)