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Two Weeks: Cinque Terre, Tuscany, Venice

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Hello!
I am planning on visiting Italy for two weeks in September. My family will be renting a villa in the Cinque Terre for about 6 days, then from there my boyfriend and I are planning to travel to Tuscany and Venice. Some questions:

- We want to rent a villa in one of the towns in the Cinque Terre and spend our days hiking from town to town and enjoying the Mediterranean. Is there a particular town you would recommend as a home base? We want to stay somewhere that is central to the other towns and has good restaurants to dine in during the evenings. If anyone has stayed in a villa they can recommend (would need to sleep 5 people) I'd love to hear!
- From there my boyfriend and I wanted to rent a car. I have never done that abroad, do you know how we would go about getting this set-up? Ideally we would want to drive from Cinque Terre to Tuscany then to Venice (and leave it in Venice the day we arrive since we wouldn't want it there).
- We were planning on spending 4 days in Tuscany and 4 in Venice. Any recommendations for the Tuscany itinerary? Should we stay the night in a different city every night as we make our way to Venice? If so, what cities?

I would be SO appreciative of any one's feedback!
Thank you!!!

Bonvoyagegirl

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