Rental cars for Tuscany

We always use AutoEurope.com for our European rentals. They are US based, very helpful/knowledgeable and often the best rates.
You can play around with their website to see what is available or call them toll free.

I do know that they no longer work with the Hertz location in Orvieto so that’s probably out for you and you don’t really have to go that far.

Either Siena or Chiusi would be fine for pick up. The only problem you might have is that the rental locations have short hours and there may not be an automatic available for you, assuming that you need.

No need to go to airport, that rental will cost you more

We picked up at Hertz Sansovino location which is a short taxi ride from Florence center. It was fine (outside ZTL) and easy driving from there but there were 2 of us- driver and navigator.

Read everything you can find about driving in Italy—parking, ZTLs!, speed cameras, insurance coverage etc

You must have an IDP- International Driving Permit that you can get at your local AA for about $15.

If you can handle the DC beltway you can handle the major highways in Italy ;)

Many back roads are also hilly roads in Tuscany, are you used to that? If not, the major highways are not that trafficked and the "slow lane" on the right is a safe shelter for hesitant drivers.

Plan your journey on viamichelin.com , checking and unchecking the "avoid tolls" and "avoid motorways" boxes on the left under the options tab.

Christine, wow, that's just what I needed to hear! Yes, I drive the Beltway all the time, and 270, 66 and 695. I'll check out that website. As long as I can get an automatic, and maneuver out of an area no worse than the upper exits of the Jersey Turnpike ( Bergen County native), I'll be fine. I was so taken with Montepulciano, I want to spend a few days in the area. Thanks so much for the advice!

Dario, Mille grazie! We drove from Florence in October 2019, got off the expressway around Greve in Chianti, then We need our way down to Multipulciano, and I didn't think it was very hilly, but thanks for the heads up. I have driven in Seattle and San Francisco. I mainly want to do the Val d'Orcia, and smaller town not accessible by bus or train. I'll start planning this summer for September/October of next year. Thanks for the great advice.

I was so taken with Montepulciano

Same.
We had planned to revisit the area this September but the car rental rates this year are sky high. Hopefully that will settle down by next year.
We drove from Florence to Siena via Chianti Road- lovely and quite easy (at least for the navigator!). We then stayed in Siena 2 nights- with car parked- you do not want to drive in to Siena!
Then we headed to Montepulciano and stayed there a few days taking day trips all around the region
Favorites were Bagno Vignoni, San Quirico, Pienza, Monticchiello.
La Foce gardens were closed when we were there but would have loved to visit.
We found Montalcino to be a bit boring, just did a walk thru there. We didn't make it to Sant Antimo but that is supposed to be lovely.

There's a Hertz location just a short walk from the train station in Siena, and as I recall it's a selection thru AutoEurope ... which we prefer since they make it clear what the insurance coverages and prices are.
If wanting to stay a night or two in Siena there's a cheap underground lot at the train station that always had space when we were there a couple of years ago. If wanting to head directly to Montepulciano it's right on the SR2 heading south towards the Val D'Orcia and Montepulciano.

I’ll agree with Christine…we rented from Auto Europe, picked up our car at the Hertz Sansovino location and so easy to get out of town and on our way to Siena. And I’ll add one more thing. As we were loading our car (loved our Fiat!), the Hertz manager mentioned that because the sign posts might have multiple arrows to different towns and highways, the easiest thing to do while leaving Florence would be to follow the blue or green signs for Siena. Can’t remember which. So helpful when you’ve just picked up your car! We also wanted to stay on SR222, winding through the Chianti region south and avoiding the Autostrade throughout our entire two weeks. Google maps worked seamlessly throughout Tuscany and Umbria, even on the smallest roads. Have a wonderful time!

Must have been same manager for us- can't remember the color either but is sure was helpful

Hertz manager mentioned that because the sign posts might have
multiple arrows to different towns and highways, the easiest thing to
do while leaving Florence would be to follow the blue or green signs
for Siena. Can’t remember which.

Having driven in Italy several times, I would have no hesitation in suggesting driving. It is no worse than driving at home. The drivers are aggressive, but also will let you merge and proceed. Stay I. The slow lane unless you are passing. I found Tuscany easy to drive, especially the secondary roads. They meander and are undulating, but nothing to challenging. Our last trip we rented after our trip to Rome near the edge of the city and drove to Tuscany.

I have used a company called Gemut, which is US based. Do not forget an international drivers license. I have been stopped in rural Italy, for a random traffic stop, and the IDL was essential.

Enjoy your trip.

Catherine, we rented from Hertz in summer of 2019. We picked up the automatic car at Hertz Firenze Sud. Very close to highway heading south. After touring Tuscany, we dropped car at Orvieto, but if I read one of the responses correctly, Hertz is no longer there, but you can check on that. Our last stop before dropping the car in Orvieto was Montepulciano and we loved it. Enjoy.

David
Hertz is still at Orvieto station but apparently due to poor service AutoEurope no longer books with them

The alternative drop off would be Chiusi also right at train station.

We went from Montepulciano to Assisi then dropped car in Spoleto (very easy) and trained to Rome

Thanks Christine, now i understand. We did same thing dropping car in orvieto, spending the night, then taking train to Rome to fly home.

In 2019 my wife and I rented a car from the Hertz office near the Orvieto train station, stayed 3 nights at a house near one of the entrances to Montepulciano, drove quite a bit in Tuscany, and then dropped the car off at Siena. I had no problem driving either on the country roads nor on the highways. The Orvieto Hertz office was very close to the train station. The Siena Hertz office was about a 15 minute walk from the train station, and a bit difficult to find. Details are in my trip report posted in this forum at the following link (Parts 5 and 6). https://community.ricksteves.com/travel-forum/trip-reports/italy-2019-sicily-sorrento-amalfi-pompeii-rome-orvieto-tuscany-siena-florence-cinque-terre-milan

You've gotten some good responses regarding logistics. I'm just here to encourage you to do it and tell you that for me this is the best way to see Tuscany. If you are a confident, defensive driver and have a record of obeying the rules you'll do fine. If find driving in Tuscany as easy or easier than driving in Silver Spring, which we do when visiting my younger son and his family.

Read up before you go. Familiarize yourself with the signage. Stay on the back roads as much as possible, that's where the fun is.

Thank you, everyone, for all your good suggestions. I'd like to visit Tuscany every Fall, I've never seen a more beautiful place.