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Croatia/Italy

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I am planning a 19-day(perhaps 16 days minus the travel time), backpacking trip to Croatia and Italy the second week of August. I am most particularly interested in sight seeing and going to places with beautiful landscapes and buildings. I would love some tips on hotel accommodations that are close to or witin walking distance to the airports or train stations.
I plan on flying to Dubrovnik and spend 5 days there exploring the city and heading up north to Istra. I know that trains are not as accessible in Croatia so any tips on transportations in Croatia, are greatly appreciated. Also, any recommendations on breathtaking spots and restaurants will be helpful and appreciated.
From Croatia, I would like to take the night ferry into Venice. I plan on staying one night there one then take the train to Cinque Terre or Florence or Tuscany. I will stay about a week around that area and explore Tuscany, Pisa, and a few other neighboring cities. From there, I will head off to Rome and do the usual sight seeing attractions and then take the bus or train to the Amalfi Coast. I know that the time I will be spending in each city is short, so I welcome any suggestions you might have that will be advantageous to my trip planning. What I am most particularly concerned about is, just the hotel accommodations that are closest to the airports(RomeAirport)and train stations.

Would it be better for me to find find three main hotels and take the bus or train to neighboring cities. I was thinking of booking in Dubrovnik for five days, one in Florence for five days, and one in Rome for six days. Not knowing the geography layouts of Croatia and Italy, would this be too much travel time on trains and buses?

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