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Need help in planning 4 days in Tuscany post -cruise

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Fellow Fodorites:

I could really use some help here. We are a group of 7-9 who will spend a few days in Tuscany after our cruise, which ends in Civitavecchia, port for Rome, in November 2014.
We would like to take the train from the port to the town in which we will base for our visit.
We are open to going anywhere in Tuscany, as long as I can spend a day picking olives somewhere (on my bucket list!). Prefer relaxed sightseeing, and wine tasting
Prefer to fly home from Rome, as flights have fewer stops, and would like to be able to take the train back to the airport
Have resigned ourselves to needing car rental, but perhaps not for the entire visit ?
Possible to take the train to our destination city and pick up cars for a day or two for day trips?
Are we better off renting a house or staying in a B&B?
Any suggestions on which town we should base ourselves in?

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