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Need suggestions for traveling out of Milan, Italy to other cities

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My dad, 80+ years old, has always wanted to travel northern Italy. His wish is to fly into Milan, then in no particular order, go to Como, Chivasso, Ottone Piacenze, Lucca, Pisa, and Cinqueterra. Our group consists of a total of 5 people.

My first question is: Since we have heard that driving ourselves out of Milan is crazy and dangerous(Is that true??) does anyone have a suggestion how we could get around? I think trains are out because we won't have transportation once we get to our destinations. Does anyone have knowledge of a company/tour guide we could take with us? We know of one person and we are looking for other options as he isn't very close. Maybe there is a solution we haven't thought of yet.???

2nd question: We'd like to stay in Lucca, and then 1 or 2 other of the above towns (not Milan). Then we plan on taking day trips to the closest towns/cities. Does anyone have suggestions for nice , but not too expensive, hotels in any of the other towns?

3rd: Are we totally crazy? Any helpful hints for this trip would be greatly appreciated.

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