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Travel to San Gimignano

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Hello Everyone! And in advance thank you for your help!
I am planning my first trip to Italy(Tuscany) this August.... where I will rent a house near San Gimignano for a week to meet with my girlfriends:)). I will fly to Milan and planning on renting a car. Hope I can handle driving in Italy, can it be worse than driving in NYC? :))
1. Is there anything I need to know about driving in Italy to avoid unpleasant surprises?
2. I am not sure how much time do I need to do Milan's highlights?
3. Before going to Tuscany, I am planning to stop in La Morra, Piedmont area for a few days. From there I will drive to San Gimignano...There are two route options : E-80 ( along the coast), how difficult is to drive there? Or take A21-Piacenza and E45 through Bologna is easier?
4. While in San G., of course we want to visit Cinque Terre. Had anyone travelled to Cinque Terre from San. G. by a car? What town in CT should I go first? Is it too much hustle to drive there? How else we can get there from San G.? I found a plenty of guided tours to CT from Florence(quite pricey) and am not sure we want to do the organized trip.
5. Also, how much time to do I need to give myself to drive from San.G. to Milan? According to Google map it's 4 hours, is it right? I need to be at Malpensa airport by 14:00 (2PM), at what time do I have to leave San G.?
Sorry for too many questions, hope you were able to follow...
Thanks again :))

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