I booked a trip which ultimately goes Munich -> Bolzano -> Verona -> Venice -> Innsbruck -> Munich
At first, I didn't think this was going to be that difficult to manage since the trains from Munich to just about anywhere are frequent. But then as I'm looking at booking tickets in what I thought was well in advance, I'm seeing that the best options are 5+ transfers and 6 hours minimum just to get from Munich to Bolzano by train. EDIT: Some of the comments mentioned that I should include the travel date - which I added in a comment to this post, but adding it here as well. I'd be traveling on August 14 from Munich to Bolzano.
I'm traveling with a party of 4 adults and 2 children (1 and 3 years old), so that many transfers is less than ideal to put it simply. We have a friend who did a very similar trip (by coincidence) a few weeks ago and she mentioned that they got to Bolzano in maybe 4 hours with one transfer in Innsbruck, but after searching just about every train booking site (OBB, DB, RailEurope, thetrainline, Trenitalia, Omio), I'm starting to think she was lying, got very lucky with timing, or I'm being completely dense about how I'm searching for train options.
I also checked Apple Maps, which does claim that there's an easy trip with only 1 transfer, but I find this hard to believe if none of the previously listed options aren't showing anything remotely convenient.
There is a bus which is more or less direct from Munich to Bolzano which has a reasonable travel time of about 4.5 hours, but then we need to bring a carseat for the 3 year old, which would essentially be useless after the trip to Bolzano and is just something we have to lug around as we continue the journey.
Any tips on how to make this work? Any other train booking options I haven't checked?