help with car rental options for Castellina in Chianti

You make sense, but I had no problems or stress driving around the florence airport. It's a small airport, by international standards, and you don't have to drive in the city center at all to get to or from it. I can understand not wanting to deal with rentals near the train station etc, but the airport should be fine. I would get rid of the car as soon as it's easy to travel by public transport.

Rent from the Florence airport. The advantage is that you will be able to leave on well-paved, well marked roads. It's not the same as driving through a larger town - even Siena is fairly big. Driving from Castellina to Assisi is easy, you'll want a good map or GPS. The terrain between the two areas is mountainous. I found it easier to drive south around Siena and then back up towards Umbria.

Thanks for the great advice, Doug and Debra. For some reason, I had an idea that renting from Florence airport and driving to Castellina from there would be challenging, but doesn't sound like it. I'm definitely leaning much more towards that option as it gives us much more flexibility, and we don't have to worry about making it to the rental in Siena before it closes for the wk-end. I'll make sure we get a good map and GPS. Now, I just have to decide whether to drop the car off in Siena (again, the Saturday time constraint and traffic issue) or after our day in Assisi as we head back to Rome. Any ideas on an easy drop-off location between Assisi and Rome? Otherwise, I'll probably just go with a bus/train from Siena to Asisisi.
Again, thanks everyone for your help.

Yes just to reiterate - Florence is not a "big" city! If you go out to the airport to rent the car, you can easily get on the A1 (I think this is the easiest way for you) south towards Rome, exiting after about 15/20 minutes to the FI-SI motorway, and from there exit to San Donato. You take a left at the end of the ramp, and the road leads straight to Castellina through some gorgeous countryside. Here is one tip - when you are off the highway and past San Donato, there is an AutoVelox (a traffic camera that checks for speed) right before a tiny cluster of building where the road narrows - you need to get down to I think 30 K an hour from the 60 posted very quickly. You don't want to drive past those machines speeding. There are also some on the FISI, so be careful! The roads in and around Castellina, Siena, Greve, etc. are mostly excellent but they can be sort of narrow in spots. And Siena is funny if you are driving, you never really seem to see the city from the road, so make sure you have a good map or GPS.

Thanks,Anthony. This is incredibly helpful information. Thanks for the speed tip and for the really helpful directions, too.

Having a car in Castellina in Chianti will be wonderful. We stayed there last month and really enjoyed the views and the area. Like the previous poster noted, it is a narrow, winding road from the autostrada into the area. Picking up the car at the Florence airport and then dropping it off in Orvieto might be your best option. Siena is quite a large city. Orvieto is smaller. There are rental car offices at the Orvieto train station. I can't remember which ones. If you are renting the car from AutoEurope, they can tell you. Also, don't forget to get your International Driver's License at the AAA office here in the States before you leave. There are no exams involved in getting the license. Just two passport type photos and $15. It's the law to have one in Italy. Have fun driving and touring the area.

Thanks so much for the post, Denise. It's good to hear from somebody that's stayed there and enjoyed it, too, and good to have the info about the narrow, winding road beforehand. I will probably pick up the car in Florence airport now that I've read these posts and my fears have decreased a little! Thanks to everyone for their help. Here is my question, now. We are leaving Castellina cottage on a Saturday, and would like to get to Asssisi on Saturday and stay overnight and spend next 1/2 day there before heading back to Rome. Unfortunately, to complicate matters,we will be going back to Rome on a Sunday and I think most rental places are closed on Sunday, so I'm stuck as to where and when to drop car off. Drop-off in Oriveto and taking train from Oriveto to Rome would be perfect, but I think the rental car offices in most places are closed on Sundays.
Any suggestions?

Double check that they are closed on a Sunday. I returned a car on a Sunday in November. It was a major holiday no less (Nov. 1) and there was a guy at the Hertz desk at the florence airport. in Rome I bet there is a place to return on Sunday. In a smaller city like Orvieto, maybe not. but you never know, you have to check with the rental company you're looking at. I believe autoeurope the available return/pickup times.

I'll definitely follow your advice and do some double-checking on wk-end hours for car rental offices.
Thanks for the help.

Marge, check with your rental car agency and find out if they have an open office on Sunday. (We just check online for dates and times that each rental lot will be open.) We picked up a car on a Sunday /holiday weekend at the large underground rental lot under the Borgeshee gallery in Rome. It was easy to get to the freeway from that location. All the majors were located there. I would not worry about driving into that location in Rome; especially on a Sunday. Your GPS would have no problem taking you there. And it is close to the Metro stop at the Spanish Steps. Orvieto is also an excellent location to drop off the car.

Thanks for the suggestions. I'm still just a little bit leery about getting anywhere near Rome while driving a car, but I'll look into the Borghese location. I've also heard Oriveto is a great location to drop off a car, but since we'll probably be driving from Assisi (unless we drop off car first in Siena), I'm wondering if Orvieto is out of the way. Any ideas? Also, has anyone had any bad experiences with using the drop-boxes at rental offices?
Thank you.