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Puglia Italy and Montenegro

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I'm thinking of taking a flight from Canada to Rome, travelling by train to Puglia, renting accommodation for a week or so and renting a car to see the sights. After that I want to take the ferry to Bar and rent a flat in Kotor as well as hiring a car. From there, after two weeks, I'd need to return to Canada. Can anyone give me some tips or information to help me with planning this trip?

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