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Advice re: Munich to Rome or vice-versa

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We want to spend a few days in Munich during Oktoberfest and then wind our way to Rome. I'm just starting to put this together (I know we may have to stay fairly distant from Munich because I'm late in planning) and appreciate all advice, including "you're crazy." We can start or end in Munich or Rome. We can leave any time between 9/19 and 10/2 in order to make the trip work. In addition to Munich and O'fest, we want to spend time in Tuscany, the Amalfi Coast, and Rome. We will have between 14 and 18 days. My initial questions are:

Should we rent a car wherever we start and drive the whole trip?

Would it make more sense to take a train from Munich to Siena or the AC and rent a car from there, or am I dreaming that there will be an auto rental office anywhere close to these areas? Or, after spending time in Rome, rent a car to see Tuscany, then the AC, then take a train to Munich?

Just to give us an idea, if we took the train just from Munich to Rome, how long would it take (ballpark)? Could/should we take an overnight train?

What is considered low season in Italy? We might try to plan with that in mind.

Munich would be 3 days tops, then 4/5 in Tuscany, 4/5 in AC, 4/5 in Rome. We are energetic seniors and we pack light. If we drive, I realize we'll have to allow time getting from place to place which may include overnights. Looking for the thoughts of the seasoned travelers on this board. Many thanks.

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