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need advice on travel thru Stelvio Pass and on to the Dolomites

We will be leaving Lake Como early on Saturday, Oct. 5. I was planning to rent a car in Milan first thing in the morning and driving through Stelvio Pass and on to the Dolomites - thinking of staying overnight in Orteisi. (would love everyone's thoughts on where to stay). The next day perhaps ride the gondola or hike for a short time and then finish the Great Dolomite Road to Cortina and then head to Maranello to the Ferrari Museum (which my husband wants to do). In an ideal world, we would drive on to Lucca that evening (October 6) and begin our 5 days in Tuscany. What are your thoughts? Is this doable?

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