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Regarding renting in Italy. The price can vary substantially. For instance, for my last trip to northern Italy I rented a vehicle in Müchen (City Center) as it was much cheaper than in Italy. Also the drive was shorter and nicer than from Milano where I rented from in the past. Definitely check renting in the city center vs airport. Expedia works good for finding something (I get their 3rd party insurance).
Also I download Google maps for offline usage which works great as then I do not have to pay $10/day cell phone access.
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