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18 days in Italy

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I am planning a trip to Italy with a friend. We are in our late forties and would like to see the major cities and also relax and drink some wine. We are coming from the USA. We would like to see: Venice, Florence and Elba Island, Rome Capri Island, and the Amalfi Coast and if we have time Sicily. I need help where to start from and how many days in each city. We will be riding the train and we'll have a driver in the South. Twenty days total with the flight days. We need some days to relax by the beach and just to sit and do people watching...Going in Sept 2014.

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