You can use your pass in your country of residence on 2 travel days. You don't need a new travel day when you don’t change after midnight but of course will need a new travel day when you use the night train from Munich to Milan. So then you will have used your second inbound/outbound journey.

Not sure where you live but you don't have to start in Amsterdam. You can also board the night train in Düsseldorf, the first stop in Germany of the night train Amsterdam - Munich. Although you would still use both your inbound/outbound journeys.

For your return you would need a third day in your country of residence. A possible solution is to work out which travel day in Germany would be the cheapest and buy a separate ticket for that (from/to the border).

By the way, if you return from Milan via Paris using TGV/Thalys: these reservation fees are high (thanks to French railways) and have limited availability.

Thanks for confirming that, appreciated. This just won't work, as i mentioned the nearest German connection on the Amsterdam-Munich night train is too far away and is very late at night. I'm traveling with the family. It's such a shame this rule exists, i will have to find another way to travel.

Als i'm not coming home from Milan, I'm coming home from Cannes.

Sorry if i sound annoyed, it's not with you, it's just the disappointment that what could have been a lovely adventure had been scuppered by this restriction

In Düsseldorf the Nightjet from Amsterdam arrives at 21:41 and starts to Innsbruck via Munich and to Vienna at 21:44. If you want to spend the day in the mountains go to Innsbruck, if you like a big city take Vienna. From Vienna the Nightjet to Milano Porta Garibaldi starts at 19:23 from Wien Hauptbahnhof. From Innsbruck you have to take first a Railjet to Salzburg (there is a train every hour) and then take the Nightjet from Munich to Milano Porta Garibaldi at Salzburg Hauptbahnhof at 22:02. 

Arrival at Milano PG at 8:10 of both Nightjets from Munich or Vienna. 

Thanks for the ideas, I'll continue trying to find a way to make it work!  You've maybe hit ion a need us i didn't see before

The problem i see with interrail passes is that, for those like me who don't live near a main connecting station, they need to get a train within their country to connect to the train out of their country. So 2 trips within their country is an unreasonable limit.  It's fine if you live in Berlin or Düsseldorf, but for the rest of us it means paying for extra tickets. Which defeats the object of an all in love inclusive pass.

But the way, do we know when the July 22 timetables are published? Right now I'm checking times and routes for May, as that's when it goes up to. Maybe there will be additional routes in July?

The connecting train is included in the interrail pass. not only a trip. You can take all the trains you need to get to the border or the airport to leave Germany. 

Within Germany you can use your Interrail Pass only 1 day to leave and 1 day to get back. This days are not extra, but for example with an 7 travel days in 1 month interrail pass you can use only 7 days in one month to travel with the train, two of theme you can use to leave and to get back home. 

Ah, so did i misunderstand? If i get the train to Düsseldorf on a Wednesday, and then connect to the nightjet to Wien hbf, can i count that as one journey in my home country? That would be awesome, as the train to Düsseldorf is quite expensive for 3 people. I do it quite often to get to the airport, sometimes, for shorter trips, it's actually cheaper to drive and pay for parking there. So ..

1. Münster to Düsseldorf +Düsseldorf to Wien nightjet and stay a night or two.

2. Wien to Milano nightjet plus onwards to Genova (i want to stay there a night or two)

3. Genova to Cannes, stay for a week

4. End of beach holiday, direct train to Paris (daytime) and directly connecting to Münster (all in one day)

= Total 4 travel days and 2 home country travel trips. Have i got that right? If so, you've just saved my holiday!

That should work.

Awesome! Thanks again for all your help @Angelo  @rvdborgt , I was pretty much resigned to finding an alternative, now I’m looking forward to visiting Vienna for the first time!