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5 women, Italy, need suggestions

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I will be traveling in Sept 2016 (for 10 days) with 4 of my female friends to Italy.

A little background - We are all in our early 40's, 3 of us have already visited Italy - albeit a decade ago. We've seen Rome, Florence and Venice (I did all the driving) We were able to experience a lot of touristy things. What we are looking for this time is some history, culture, wine, food and FUN (some nightlife)...I ask them and all they say is they want to sit in a piazza, people watch, drink some good wine and visit some sights.

Any suggestions for areas to stay that have charm but also central to visiting other areas? Are we better off staying in a city and then traveling to charming towns or vice versa? We have little experienced of the public transportation but that is also possibility. Maybe ever stay one place for a week and then a few days somewhere else.

Please help me narrow down the possibilities!
Thank you!

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