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which city to work out of as a base

We are traveling to Italy in early June of this year (2011). Thoughts on the following trip to Italy (June 8th through the 25th) would be appreciated: 1. We arrive in Rome on June 9th and leave by car on the 14th. We are staying inan apartment in Trastevere for five nights. 2. June 14th We plan to stop late that morning in Orvieto on the way to Assisi, we will have lunch and spend a few hours. 3. We are staying in Assisi the night of the 14th and 15th. 4.We will leave Assisi the morning of the 16th. We would like to stop to see Siena ( Pisa is questionable as my husband and I have both been there but are girls have never been to Italy...yet the comments I have read are to skip it) 5.Then Florence with the idea being we leave Florence on the morning of the 19th to drive to Venice. 6.We stay the 19th and 20th in Venice. 6.The morning of the 21st we leave Venice and stop in Ravenna for lunch and to look at the mosaics. 7.We then plan to drive to Agnone and Pietrobbondate in Molise to end our trip visiting with family in our family's hometowns. This would be the 22nd, and 23rd. 8. The morning of the 24th we would drive back to Rome through Raino (east of Rome) to stop and visit a cousin in the afternoon and then spend the final night somewhere outside of Rome to make an easier commute to airport the morning of the 25th. 9. June 25th We have an 11:30 am flight back to the states. So my question is where should we stay in between Siena and Florence ? Should we stay in one or the other city and make daytrips in and out on the 16th, 17th and 18th? Or should we stay in an area in between. Also everyone keeps talking about the trouble getting into Florence by car...should we be concerened?
Grazie tutti

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3313 posts

You've touched on issues that are frequently discussed here; driving in Italy, driving in Florence, and where to stay in Tuscany. With a car, I'd look for an agriturismo between Siena and Florence. You'd be in the Chianti region and there are many small towns to explore. You can drive to parking just outside the central parts of Florence and Siena. The reason you hear about trouble getting into Florence by car is that the center of the town is off-limits to cars except for residents. Traffic cameras record the license plates of cars entering and citations are sent by mail to violators - or their rental car agencies. Finally, you need to get an International Drivers Permit to drive in Italy. No big deal. They're available at AAA for $15. They're just a translation of your drivers license so the Italian police officer knows which box is your name and which box is your hometown. But Italy requires you to have one - along with your drivers license.