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Munich - Austria - Czech Republic and Italy !

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Ok, I'm very lost trying to organize my trip so any help / suggestion will be very much appreciate .
We are going to be in Munich and we are looking to go to Vienna, Praha, Venice Florence and Rome.
Munich has to be our starting stop as my sister is based there and my mom is flying to there, I know Vienna and Praha are not that far, but what about Italy . Don't mind if we have to fly somewhere, we are pretty flexible about buses trains etc .
I thought about flying to rome , then train to florence and venice .
Then maybe train / bus ? To Vienna and then to Praha , to head back to Munich?
Please any help will be really appreciate .
We are considering any option if it turns to be quicker or cheaper .
Also regarding accommodation, last time I went to those cities ( +10 years) I remember as soon as we arrived to the train stations there were a lot of people offering hotels etc for a very good price and they all were very good . I know now with internet it might be different but just in case , is that still the case?
We are trying to have some flexibility and advanced booking probably won't help!
Again thanks for any help !

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