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2 week itinerary for Italy

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We are planning a first trip to Italy for the last 2 weeks of October. We are planning 3 nights at the beginning of the trip in Rome and 3 nights near the end in Cinque Terre. We were thinking about spending the balance in Tuscany and would appreciate suggestions on places to go or stay. We are considering 2 to 3 nights in Florence and a couple in Sienna and the rest is open.
Also, does one need to rent a car for the Tuscany portion of the trip or can it be done by train? Any winery or olive oil trip suggestions would be appreciated.

thanks,

Don

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