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Traveling in Tuscany

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After staying in Monterosso, Italy in May, we are going to stay 4 days in Cortona in Tuscany. There are 6 adults in our party. In order to visit places like Siena, Florence, Lucca, Venice and see a bit of the countryside, should we rent a vehicle, such as a van, or would we be better off maybe renting for only one day, and traveling between Siena, Florence, etc. by train? Is is better to book car rentals from here (Canada) or can we wait until we get to Italy? Any suggestions?

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