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Itinerary Help for Tuscany

We did our honeymoon in Tuscany and Rome and now over 20 years later, we want to take our adult children there. We plan to fly into Rome around Dec 23 and stay for 6 nights and then stay in a second location for 6-7 nights from which to do day trips to see San Gimignano, Cortona, Florence, Siena, etc.

It seems most would use Florence as the 2nd base but my husband and I prefer smaller towns and would prefer Siena as the 2nd base. We would like to explore the option of renting a car for our 2nd half of the trip. I understand we can't drive into many of the smaller villages having to park outside the city walls which is fine with us. But, how feasible is it to do that?

Can we stay in the center of Siena and just cab to where our car is parked daily? I've read the underground parking by the train station in Siena is a good parking place.

Does it make sense to do this or is it better to use Florence as a base and take public transpo to these smaller towns instead of renting a car? Or is it better to rent and drive to and from Florence? My husband and I really enjoy the flexibility of driving, but want to explore the best way to do that logistically. Thank you in advance.

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8386 posts

Siena is a great base for exploring Tuscany- and a car is almost necessary as public transportation to most hill towns is slow and complicated in some cases.

You could train from Rome to Florence- spend a night or 2 then pick up car to head to Siena- multiple threads here explain how to drive out of Florence safely
or just go to Siena from Rome (bus is easier/quicker) and rent the car once there only on the days you actually need it. There are several rental agencies near train station.

There are hotels with parking in Siena
We have stayed at Palazza Ravizza- very nice with onsite parking and fantastic views. Hotel Athena is right next door- also has parking and same view
Both easy walk to Il Campo.

Driving in and out of Siena can be a but dicey as you will have to be careful to avoid ZTLs- your hotel can help with that.
Day trip to Florence via bus- quicker/easier than train.
Driving in the region is easy and enjoyable- parking outside the walls of smaller hill towns also easy.

Make sure all drivers have an IDP (required by law) and read up on driving in Italy.
We always book our cars with AutoEurope.com- consolidator with excellent customer service and often best rates