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Italy Itinerary

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Hello!
My husband and I are going to Italy in July for about 2 weeks. Here is what we are thinking:
Day 1- Fly into Venice check into hotel, get a lay of the land
Day 2- tour Venice
Day 3- train to Florence, check into hotel, explore
Day 4-5 Florence
Day 6- pick up car in Florence- drive into Tuscan county side, check into home base
Day 7-9 Tuscany
Day 10- Drop off car, train to Rome
Day 11-14 Rome
Day 15- Fly home from Rome
This is a very loose itinerary. I want to know if the timing of things makes sense. I am also curious about car rental. Should we rent in Florence and drive into a hill town? I would like to stay in one place in Tuscany and make day trips, which is why we wanted a car. We want to go to Siena, but we are open to other suggestions. We love food and would love to tour a place that makes cheese or olive oil. We would like to tour a winery or 2, but mostly take it all in and relax, go on nice walks. Where should we drop off the car and hop on a train to Rome?
Should we spend an extra day in Florence and one less in Rome? Thanks in advance for your time and advice!

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