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Drive from Chianti Florence to Positano

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Hi all,

We are planning a trip in May and have a very long travel day to get from Chianti Florence all the way to Positano. I was wondering if anyone had two or three good rest stops that were along the way. Ideally split evenly between the two with one on the Florence side of Rome and the other on the other Positano side of Rome.
I have heard of Herculaneum as a possibility, however, I have no clue to the Florence side?
We are traveling with 4 adults and are pretty open to everything except the typical Church/indoor museum type stop as we would like to get some fresh air and stretch our legs.
I am looking forward to hearing all of you wonderful ideas!

Wendy

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