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18 days in Southern Italy

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We have planned a tentative itinerary for travel at the end of September 2016. We arrive in Rome (from Canada) and plan on spending 3 nights. Then we will take a flight to Bari and spend 4 nights in Puglia. We plan to spend 2 nights in Lecce and another 2 another spot not yet determined in Puglia. We will then drive to Sicily staying 6 nights distributed among Taormina, Siracusa, Agrigento, and Palermo. We will then take the overnight ferry to Naples and spend 3 nights in Naples. Then back to Rome for our flight home.
Here are my questions:
1. When in Puglia where would you suggest we base ourselves for the other two nights?
2. Our one long driving day is from Puglia to Sicily. Is this doable? Will there be a delay in crossing Straits of Messina?
3. We plan to rent a car in Bari and drop it when we arrive in Palermo. Does this make sense?
4. Any suggestions for lodging in Sicily?

Thanks in advance for suggestions and advice. This is our second trip to Italy, the first was 40 years ago and we only visited Venice and Milan. We are very excited to be returning and spending 18 days.

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