Train Passes and Discount Cards Through Europe

The trip includes the a night train between Munich and Prague

I am unaware of any such train. It is a 5 1/2 hour direct train during the day and there are 7 of them, every 2 hours starting at 4:44 am.

Where does the Bernina Express fit into this itinerary?

Are you taking a train from Prague to Basel? Maybe this is the night train you are referring to.

I'm sorry, I misspoke! I meant to say night train from Prague to Basel. The Bernina Express is at the end of our trip. We're headed to Chur from Basel, then takning the Bernina to Tirano and spending the night in Milan before flying out.

How old are the kids?

In Switzerland, with the Half Fare Card now at 150 CHF, you need 300 CHF worth of full fare tickets to break even. You only have 137 CHF per adult for Basel to Chur and Chur to Tirano, so that would not help. One thing that would help is to not take the named Bernina Express, but travel on the regular trains. That will save you 4 seat reservation fees at 36 CHF per person. The regular trains are less crowded, have windows that open for better photos, and you can hop on and off if you like. You will have to change trains at least once between Chur and Tirano.

You could price out the Eurail Pass for what you want to do. Remember, on night trains you will still have to pay full price for sleeping accommodations on the train with the Eurail Pass.

It's not what you asked, but for a two week trip, that's an awful lot of travel.

Yes, it's a train-centric trip. More of a backpacking type of experience.