Should I rent a car in Rome and drive to hill towns on my way to Florence or take train?

I would do Rome to Florence. But, don't drive in Rome. Rent the car at the airport, or some other location outside town. A friend trained to Orte, or you could do Orvieto, and rented a car there. Your towns are easy off the A1.

Florence back down would be a bit more confusing I think. But, it can be done either way. Rent the car at the airport, I tried driving once in Florence, never again!

We did something like the opposite. We rented a car in Florence, then spent five days with a base in Montepulciano, dropped the car off in Orvieto, and took the train to Rome.
I would recommend taking the train to Orvieto. It's about an hour and fifteen minute ride. There is a Hetrz office about a five or ten minute walk from the station. From there, it's a few minutes to the A-1. Montepulciano is about an hour and twenty minutes beyond. If you will be in Montepulciano just for the day, check out the parking areas beforehand, so you will know where to head. There are shuttle buses that will take you to the Piazza Grande at the top of the hill if you don't want to walk to the top, but if you are up for the walk, there are lots of interesting things to see. ( you can always take the shuttle up and walk down.)

I would rent a car after Firenze and turn it in before Roma. Staying in Firenze first will give you access to more information about what to see in Tuscany.

Since you are starting in Rome, rent the car away from the center. I personally think this is easier to do in Rome than in Firenze, but others may have had other experiences. When I rent, I use a Hertz outlet on Via Guido d'Arezzo where it is easy to escape town to the GRA and A-1, where traffic is not too intense. You can get to the Hertz location by bus or tram.

Joe,

Keep in mind that Italy in December may be on the "chilly" side, so you may not be getting much "pool time" at the Agriturismo. In some areas in the north, you may also encounter winter driving conditions.

A few points to keep in mind with car rentals.....

• Each driver will require the compulsory International Driver's Permit, which is used in conjunction with your home D.L.
• You'll need to be especially vigilant to avoid the dreaded ZTL (limited traffic) areas which exist in many towns. Do NOT drive in Florence as it's just about saturated with automated ZTL cameras.
• You'll also need to be vigilant to avoid automated speed cameras, including the Traffic Tutor which measures both instantaneous speed as well as an average between two points.
• Keep change handy for tolls on the motorways.

Joe, We visit the hill towns every time we go to Italy and as public transportation is just about nil renting a car is the only way. We stay in an Agriturismo in Penza and plan our daily trips from there. As to renting a car in my book there are only two choices. First of all make reservations from the US with one of the major car rentals. As to which city to use, if you chose Florence leave from the airport and avoid the city center offices. The other city is Siena, the Hertz rental is very close to the train station. I drop my wife off at the station, return the car and walk back to the station. I prefer Siena as we usually stay there a few days before getting a car. Hope this helps. Dean from Oregon

A car is great for Tuscany but that is if you have some time for Tuscany. Just one day in transit to Florence doesn't seem like enough. Any way you could devote 3 or 4 nights on the road between Rome and Tuscany? We have done Tuscany by car 3 times -- once for a week 35 years ago, another time for a week about 15 years ago and a couple of years ago for two weeks with an apartment in Montepulciano. This was heavenly -- although perhaps not quite so much in December. For a one day trip especially in Winter, I am not sure I would bother although it can be done. It is easy to avoid the ZTLs in hill towns because they are very well marked as is the tourist parking very well marked. You park on the outside of the historic center and then walk in. We like to pick up the car at FCO to avoid restricted areas and traffic in Rome. You need to drop the car before Florence or if in Florence at the airport as it is VERY easy to get tickets even if you think you are on an authorized path to the rental agency. Stray into the bus lane and then get confused and go around the block and you can end up with 3 or 4 tickets
very quickly at 100 Euro or more a pop.

If you will be at the agri near Siena for several days then the car will be great to have, you could drop it in Siena and bus to Florence FWIW I would not stay in an agriturisimo outside of Siena at that time of year; I would get a hotel with a parking lot inside the historic walls. Palazzo Ravissa and Hotel Athena are two that have parking and are within the walls. That way you have beautiful Siena and its restaurants in the evening instead of being stuck on a dank farm in winter.

How many days do you have in total for Rome to Florence ??
Day 1 Train Rome to Orvieto
Day 2 Pick up car in Orvieto (early am) and drive to Siena (via Montepulciano and Pienze)
Day 3 Day excursion to Sam Gimignano and Volterra
Day 4 Return car in Siena (early am) and train to Florence (late pm)

Mahalos to everyone for the suggestions.

Current plan has us renting a car in Rome, four days for Hill Towns, staying in hotel in Siena (as a base), returning car in Siena and bus to Florence.

Much appreciated! A huge help!