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First trip to Italy. Have a few questions.....

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Hello, my husband and I are planning a two week trip in Sept. 2012. It will be our 20th anniversary, so we want to splurge a bit, and we want it to be really romantic. When I first started researching, I was a bit overwhelmed, because it seems like there is so much to see and do! We have decided to focus on three areas, Venice, Tuscany, and Amalfi Coast. We will have to leave the bigger cities for another trip, and I'm sure many of you think it's crazy to not visit them on a first trip, but I'm trying to go with my gut, and go with what interests us. I can get the best airfare/shortest flight flying in to Venice and out of Rome. So here is my itinerary:

Fly in to Venice- Venice 3 nights
Travel to Greve In Chianti- 4 nights -rent car and explore
Travel to Positano- 3 nights
Travel to Capri-2 nights
Travel to Rome-1night and leave the next morning

Does this itinerary sound doable?
Also, do I need to plan my travel between spots via train in advance, or do you just show up at the train station and purchase tickets? We would like to rent a car while in Chianti, should we rent in Venice and drive there or should we take a train and then rent somewhere? Also, the last night in Rome, should we stay near the airport, or could we stay in Rome and soak up an afternoon and evening there, and would we be able to get transportation in the morning to make an 8:00am flight? I realize we won't be able to see hardly anything, but I hate to think of my last night by the airport. Any help for this Italy newbie would really be appreciated!

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