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Italy Vacation

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Hi Fellow Travelers
I will be traveling to Italy Sept 2018 with the thought of visiting Cinque Terre 3 days, Milan 3 days, Florence 7 days (with day trip to Siena} and finally 7 days in a agriturismo somewhere near the border of Tuscany and Umbria. So, question 1....should I overnight outside of the Cinque Terre or in one of the 5 towns? Question 2...any recommendations on an area for the agriturismo to take advantage of Tuscany and Umbria hill towns? Lastly, my wife will be returning home after three weeks and I will continue for an additional 2 weeks. I will spend the final week in Rome before returning home but for the previous week, I am looking for a beach week. Question 4, any advice on this week? This would be the 1st or 2nd week in October. During this trip, I will take advantage of both train and auto. My plan is to fly into Milan and out of Rome.
Thank you

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