Renting a car in Tuscany Italy

All rental car info is below, including insurance. Read all.
Rent from these two consolidators (both part of same corporate group) and you will do good.
www.autoeurope.com
www.kemwel.com
You cannot decline insurance in Italy. You can only choose if you want to have full coverage or not. For no deductible insurance select the zero deductible option (aka no insurance excess).
Don't forget to get your International Driving Permit at AAA.

Americans who don't speak Italian rent cars in Tuscany all the time and don't have any problems or difficulties. I did it a few years ago. I was staying in Siena and rented a car for two days to explore the countryside. The first day I drove south to Montalcino, Pienza, and the surrounding area. The second day I drove to Volterra and San Gimignano. I had GPS provided by the rental agency, and I'm very glad I did. Your iPhone GPS would work, but be aware that downloading maps can use a lot of data, so you should look for an app where you can download the maps ahead of time.

Parking in Siena can be challenging, as cars are not allowed within the main tourist area of the city. (You need to be sure you don't enter any ZTL areas.) Here's a page that gives a good rundown on parking in Siena. I was able to find free overnight parking in the area just west of the Fortezza Medicea on Viale Vittorio Veneto. But if you only rent the car for one day, you won't have to worry about that. I don't remember which agency I rented from, but an easy web search should help you find and compare different agencies to make the best choice.

Some people rent in Florence, but since I didn't, I'll let them add comments about that.

Many people arrive at the towns by car, so there's always parking available (typically in pay lots, but sometimes for free on the street if you're willing to walk uphill a ways).

Your credit card may provide CDW insurance; if so, don't buy it from the agency. Read your cardholder benefits or call them to ask.

It was easy navigating and getting around, and the countryside is beautiful, so don't be nervous! You'll love it!

You can pick up the car in Florence or Siena. It depends on where you intend to stay and at which point you want to start renting a car. Do not rent a car while staying in Florence. The city center is forbidden to to non resident cars. If you pick up the car in Florence, do so when you leave town to go to your countryside destination. Siena has similar traffic restrictions. So having a car while staying in Siena's city center is not a great idea either. While with a car, it would be good to stay in a small town or a villa hotel or farmhouse out in countryside in the area near Siena.

marchantm,
This may give you some ideas http://www.slowtrav.com/italy/tuscany/hs_planning.htm

I just returned from an 8-day trip to Tuscany with a rental car. I put 1000k on the vehicle... It was pretty intense. You must be bold and assertive to drive in Italy.
A GPS is a must. I used my iPhone with Google maps and it was a godsend. I bought a 300mb international data plan and used 200 on our trip, mainly on the journey from Milan to Montecatini and back (3.5 hours each way). It also helps to have a navigator in the passenger seat helping watch out for signs and counting exits on the roundabouts.
I would not recommend driving in the larger cities -- we took the train into Florence, for example. The parking and no-car zones are just too much of a hassle. But for smaller towns that don't have convenient train service, a car is nice.
But again -- it is not for the faint of heart. There are a lot of trucks in the right-hand lanes on freeways, so you spend time in the fast/left lane. But then cars come whipping up behind you at 100mph, and you must move over, then back when you get behind a slower car/truck. It is illegal to pass on the right there, so you must be on guard at all times to get out of someone else's way if they want to go faster than you.
While it was definitely white-knuckle, it was also really refreshing in that drivers are not aggressive or angry, just assertive. Lots of faster drivers passed me, but not a one glared at me or gave me the finger for being in their way. Brush up on what speed limit and no-access signs look like, though, for safety.
Definitely get the insurance and ask what your credit card provides. I had an insurance that still had a deductible of 800-1800Euro, (you can buy 0-deductible insurance) and that weighed on my mind the whole time.
Because it's so intense (and I'm a very confident, assertive driver here) I probably won't get a car again. The trains are so good, you generally don't need one. But if you are going to do it, Tuscany is probably the best place for it.
Just be prepared and pay attention at all times.
Returning the rental car to the Milan airport was a total disaster -- nothing is marked. Both me and another person I met during my week both circled the airport three times before we spotted the "car hire" sign for car rental returns. I was so glad to have washed my hands of the rental car, I immediately went to the bar and had a big glass of vino!

Good luck and have fun!

Train to Chiusi from Rome. Pick up your rental there.

I have to offer a rebuttal to lcarter. I wouldn't say renting a car in a foreign country is entirely stress-free, but if you are primarily driving on smaller roads to Tuscan hill towns, and renting locally and not driving to Milan at the end of your time in Tuscany, you probably won't have the same amount of stress lcarter had.

I've driven rental cars in France, Sweden, Italy, Croatia, Slovenia, and Bosnia, and mostly completely on my own. Yes, it can be stressful to get lost or be stuck in traffic or in deal with a sudden downpour, and driving is not as relaxing a way of spending a vacation as just relaxing. But don't let that stop you. I don't think it's likely your experience will be as intense as lcarter's.

You're right, Lane. I didn't mean to sound too dire. I heard a lot of warnings before I did it, and I was probably overstressed because I had my 3 elderly relatives with me and felt protective of them.
I agree, the small-town driving will probably be fine. I guess my main point is that you must be on-guard there if you don't know the language, rules of the road or traffic laws. Educate yourself beforehand, drive assertively but carefully, have a GPS and you'll be fine.

Just had to add comments to renting a car in Italy. First, a bit of background: I am a 60+ male who has NO driving infractions since I was about 19 years of age. My wife and I rented a car in Umbria and dropped it off in Florence. All went very well during the 3 days we had the car. Used our own GPS, enjoyed the roads of Tuscany, etc., stayed in hotels with parking included. As we were returning the car on a Sunday (probably a bad decision), we had to return to the Florence airport. Our problems began when we passed a gas station near the car rental return and didn't see another one. I tried to reverse course and got lost a few times. Some time in that mess, I received two tickets. Here's where it got dicey. Hertz had sent us a note that they were asked by authorities for our info so they could send the tickets to us. Hertz charged my credit card 60 euros (that is 30 euros for each ticket - as they apparently had to send info twice. We are Canadian so a hefty price: 88.00 total). I have not yet received the ticket(s), looking forward to that, as you can imagine. My advice: be very careful when driving anywhere, read fine print of contract (apparently Hertz has this in contract, but not amount they will charge for sending your info), and thirdly, maybe just take trains and buses. We also did train quite a lot and had no problems at all.