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Umbria & Tuscany

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My husband are will be traveling to Rome for two nights, then to Umbria for two nights, Florence for two nights and Tuscany for two. We'll be renting a car in Rome for travel to the other areas. If we stay in Florence, where can we park overnight?

Also, should we stay in Perugia or Cortona proper, or on the outskirts. Same with Siena.

Thanks

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