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Northern Italy in 10 days

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My husband, 8 month old son and I plan on visiting northern Italy from June 6-16/18 . (10-12 nights)

We are arriving from Nice and would like to visit:
- 2 nights cinque terre (staying in Levanto): here, I am having a very difficult time finding trains from Nice, I know there are two change overs. I am see aching on both rail Europe and trenilita. I am looking for an early train out and cannot find the appropriate connections.
Is this something I should pre-book, or wait until we arrive
Any suggestions on why I cannot find the connecting trains/which station makes most sense

- 4 nights Venice

- 2 nights Rome

- 2 nights Tuscany - any recommendations on location? We want to do wine and food and perhaps stay at a winery estate.

We are hoping to do all the above by train. But can rent a car in some places- like, throughout Tuscany. Am I being unrealistic? I have heard of some people flying from nice to Venice and back tracking, seems odd but, is that a smart option?

Your hep is greatly appreciated.

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