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Italy Itinerary and Train- Please Help!

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Hello everyone! My husband and I will be arriving in Rome on Aug. 31 and departing from Milan on Sept 12th. We are adventurous (at least we think we are) and love art, music, culture and nature, so it appears Italy is the perfect destination! That being said, there is soooo much to see and so little time, so far this is what our itinerary looks like: Rome->Florence->Cinque Terre->Venice->Pula (Croatia)
->Milan. I'd like some advice, I feel like we're missing out on other places and just sticking to the touristy places. Also, our biggest concern is the train system; I am soooo confused by the types of rail passes (i.e. flexi pass) vs. point-to-point passes, I'd like to know what might be the best option. All help is much appreciated! Thank you in advance :)

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