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help- newbies to international travel- Italy logistics

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Hi,
These forums are full of terrific advice- and I am so looking forward to your insight and experience! My friend and I are joining my daughter who is studying in Italy for a trip to see and experience as much as we can in 11 days. We have the itinerary- but are really stuck about train and car arrangements.
We are spending time in Rome, then taking a train to Florence and then would like to have more flexibility in our travel for tuscany - 2 days in Pienza (home base) and the surrounding area. To that:
1. We are concerned about trying to get a rental car in the City of Florence and getting out of the city easily. Should we get a rental car outside of Florence? if so, where? Would we be best off taking a train for example to Chiusi and getting a car there?
2. For the two days in Tuscany- we want to spend time at great restaurants in the hill towns- would we be best off getting a car service in Pienza for that? Are those outrageous in price?
3. AFter the two days in Tuscany we are heading to Cinque Terre. Should we drop off our Rental at La Spezia or somewhere much closer to Siena? How hard is the drive to La Spezia ?
4. Any suggestions as to the "must do" towns and restaurants in Hill towns of Central Tuscany?

So excited to do this trip- on our own!
thanks very much,
Lisa H.

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