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Italy into Austria - Most sensible plan?

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Hello again,

Apologies that I separated the queries because I don't wanna complicate things.
I would like to know which makes more sense.

I will be from Venice (previously from Switz). I have an option to stay in Venice on the 25th October or follow my family to Milan where they will fly off back home.

I plan to go to Salzburg, then Vienna.

However geographically wise, entering Austria from Milan would be such a waste of time since Venice is nearer. So far, this is what I gather from all the stuff I read. Problem is would the train connections be troublesome or expensive here as compared to perhaps, Milan-Innsbruck-Salzburg?

Can someone advice me on this? Which is the wiser choice to make? Stay put in V or go to M and take it from there?

Excited.

All things good,
Isk.

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