Renting a Car: Florence - Tuscany - Pisa

A care is a useless hassle while you are in Florence. Most travelers reporting in here, if they are headed to Tuscany, pick the car up on their last Florence day, as they're leaving Florence.

I don't think we've figured out a perfect solution to the car in Florence problem.
Roberto might have some suggestions, since he used to live in Florence.

Some travelers reporting in here pick the car up at the Florence airport, even if they are not flying out from the Florence airport. Others pick the car up in Siena.
And some pick it up in Florence but they try to avoid pick up locations that are located where they might accidentally drive through a ZTL on their way out of town.

An extra word on needing an automatic: As you probably know, almost all rental cars in a rental car lot in Italy are manual shift. Here this issue would never come up. We've had reports here (and it's happened to me but not in Italy) from travelers who checked the box on the online rental form that says "I want an Automatic", and then they get to the lot and there simply is not one available.

I'm not sure how to avoid this. In the UK, which is the only place I want an automatic, I call the actual rental location 3 days before I need to pick up the car and bring their attention to the fact that I have requested an automatic, and that has worked in the UK but there is no language problem. I haven't had to attempt this in Italy because on the rare occasions that I drive in Italy the manual shift car is ok with me. I'm getting at the language problem.

I pass this on for whatever it may be worth.

Sorry if I wasn't clear: I will only be picking up the car in Florence to drive to the Crete Senesi (or wherever I stay) -- I do not plan to actually use the car in Florence.

So I am hoping to figure out what pick-up/drop-off locations will be the best, considering factors such as: timing (extra time needed if I have to take public transportation to Siena or wherever for pickup and dropoff), accidentally driving in ZTLs, where I am more likely to be able to get an automatic car (I assume Florence/Pisa will have more automatic cars available than Siena?), etc.

Lopa,

Just a thought... do you have any friends who drive a manual shift car so they can teach you before your trip?

It's really not that difficult to drive a manual car.

The Crete Senesi is kind of south. It's basically the area of the Val D'Orcia. Whether it's good or not logistically depends on which towns you want to visit. It's good for Montepulciano, Montalcino, Pienza, less good for towns more to the north, like San Gimignano, Volterra, Lucca etc. Closer to Siena, around Monteriggioni would be my choice, as you are closer to the freeway. But everywhere in Tuscany is beautiful, it only depends on which places you want to visit.
Pick up location is not that important as there is no risk of being fined while exiting the ZTL. Cameras are only at entry points. All downtown rental agencies are on via Borgognissanti. You just drive straight west to piazza DI Porta Al Prato and you are out. No cameras.
There are other locations a bit farther from the city center, which would be good to get on the freeway to Siena. Europcar has a location on via del Gelsomino at the corner with Viale del Poggio Imperiale. That is very close to the freeway to Siena or the A1 to VALDICHIANA exit (near Montepulciano). Hertz has a location on via del Sansovino, also good to get on the A1. All other companies only have the Borgognissanti (historical center) or the airport, which generally costs more if you pick up there. I don't know which location has a higher chance of having automatics. Italians (including yours truly) won't drive or buy automatics, unless they have a disability, and everybody there knows how to drive stick because if you take the driving test on an automatic, the DL will say that you can't drive manual transmission (basically the DL labels you as disabled). Since it's hard to resell automatics (not enough disabled Italians) rental companies keep in their fleet only a very limited number of automatics to satisfy the demand from American tourists who can't drive manuals, therefore they are very limited and likely only at locations where Americans are more likely to rent from, i.e. Ognissanti or Airport. Call ahead to confirm. I don't think Siena has big enough offices for them to justify a large number of automatics. I think Florence will have more.

Sounds like learning to drive a manual car is my best bet!

I'm asking a friend if he is willing to teach me to drive stick shift... I'm a little worried that he's going to say no because he has a nice sports car, but here's to hoping!