Thank you everyone for your input. I think I will start in Venice take a train to Lake como, stop in Verona on the way to see Romeo and Juliets balcony and then to CT and finally to Florence/Chianti. Alot of the flights I am finding out of Florence are 6am, any one flown out of Florence at that ealy time? how is it?
As of last year the shuttle buses to the airport did not start running until 5:30 a.m. For a flight as early as you are talking about (Italy seems to be famous for these sunrise departures), you probably will have to ask your hotel to arrange for a taxi to take you to the airport, the average 2006 price for that taxi ride was about €20.