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After Visiting the Italian Lakes

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Spending 3+ weeks in Italy with first part of trip consisting of 3 days in Lake Como. After that, we will have about 4 days before we meet up with another couple back in Milan for the remaining 2+ weeks. My question is where do we visit for 3 days before the remainder of our trip? We will pickup a van in Milan and will be renting a Villa in Cortona where we will visit some hill towns and then a villa in the Sorrento area before we finish in Rome. We have already been to CT, Florence, Venice, Portofino and the travel for the 3 days must be by train. Any ideas - very open to suggestions.

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