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Itinerary review needed

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I would need some advice on my itinerary below.. Is this feasible? Would you suggest if I should get a railpass? and should i also get a cross country passes?

I am starting to look at accommodations and I am going crazy. any recommendations on B&B in each locations? I am travelling with my husband. we want to stay near train station as we are not driving. anything below $150 is nice. Any recommendation?

30 May – arrival ard 705am in Rome <3 D 3N
2 June – move off via train to Naples < 2D 3N
5 June – train back to Rome and fly to Amsterdam < 2D 3N
8 June – overnight train down to Prague < 2D 2N (departing 1901pm?)
11 June – overnight train down to Venice < 1D 1N (departing 1714pm?)
13 June – train down to Florence <3D 4N
17 June – train back to Rome and fly back home (departing 2240pm)

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