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Tuscany scenic drives help

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I am going to rent a car in Florence for four days and drive south towards Montepulciano and then drive to La Spezia to catch a train to Cinque Terra. I would like to spend the night in Siena. I cant decide if I should spend one night in Siena going down and two nights in Montepulciano or two nights in Montepulciano and one night in Siena on my way to La Spezia. My husband and I enjoy driving and stopping along the way. Any suggestions would be appreciated.

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