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driving in italy

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My husband and I are planning a trip to Italy in September. This will be the first time back in 28 years. We toured that time. My plan is to Fly into Milan and rent a car, go to Tuscany, and rent a villa for approx 4/5 nights. We would do day trips to Lucca, Siena,
Puglia, and possibly on other destination. Leave Tuscan drive to Rome and return the car.
Spend 2/3 days in Rome. The fly to Sicily and spend time with family. OR drive down to catch the ferry with the car. Any suggestions would be very helpful. We want to enjoy our time (about 16 days) including flying. Or the train has been suggested. ANY help would be
welcome. CIAO

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