Renting a car from Florence to tour Tuscany

From Florence I would take E35 to SR222 and drive south toward Sienna. A beautiful route through the heart of Tuscany and the Chianti wine region

And that region is completely different from the road trip around Montalcino, Pienza, and Montapulciano - you must drive both !

Thank you so much! Appreciate the info. Would you do two separate road trips if going South toward Siena and then Montalcino, Pienza and Montapulciano?
Reading about renting a car, what is ZTL zones?
Thanks
Joy

ZTL zones although not a perfect translation or explanation I like to call them Zone Traffic Limited
which basic is a commercial or local resident driving area, similar to how in major cities in the US we have resident only and commercial only parking areas, these are areas where only commercial vehicles and local residents can drive.
Driving into one without proper permission will need to hefty fines (think hundred of Euros per violation) and each of them have a sign along with license plate cameras so need to be taken seriously.
In Siena and the smaller towns you may be visiting, just don't drive inside any walled areas, stay on the outskirts of the walls and there should not be any ZTL's to worry about.
In larger cities like Florence and Rome what is and what is not inside a ZTL is much more confusing and why most recommend not even attempting to drive in either city.

Google what the sign looks like, there are a couple of variations but you want to know in advance what to look for.

The ZTLs are perfectly clear in the smaller towns and there are big blue parking signs pointing to tourist parking. The place where it will get you is Florence. I would pick up the car at the airport so you don't inadvertently stray into a bus lane or into the ZTL and go around the block a couple of times and end up with hundreds of Euros in fines. It is very easy to do.

While you've been told about ZTL's, here's two more nasty things about them.

1) Every single time you enter one, you get a separate fine. If you're lost and go in and out of the zone three times in ten minutes (easier to do than it sounds, given one-way streets), you get three fines.

2) The fines come in installments. First, you get a fee of about €45 from your rental car company, for reporting you details to the authorities. Then, months later, the actual fine arrives, often €100 or more, and since it's late if often comes with some interest/penalties.

Not sure why people are afraid of the ZTL in Florence. It's better marked than any place else. In addition to the sign they also have a red light that is on when the ZTL is in effect (turns green at night) and a very visible camera apparatus overhead. What else do people need to understand they cannot pass that point?

Roberto I agree. During my first visit I was petrified about the ZTL but after experiencing looking and careful driving I have concluded just keep your eyes open and all will be fine.