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Need advise on travel plans train or rental car

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Im flying into Vienna and taking the train to Venice. Undecided about renting car or continuing on train to bologna, florence, assis and rome. Also undecided if Pisa is worth going to this trip. Wil spend 5 days at these sites. Then will go to Naples. Debating on taking ferry or train to Palermo. If we rent car we can take on ferry and have to drive on sicily. Otherwise it will be train on sicily and back. Looking at going back from Messina to Salerno then Naples to Rome instead of Palermo to Naples- Sorrento -Naples- Rome. Have 4 days here.
Any thoughts or suggestions.

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