Which city is the most straight-forward to rent and return a car in the Tuscany region?
I like renting in Florence. They seem to have the biggest variety of cars and vendors.
Donna
I think I rented from the Pisa airport. Years ago but I remember it was very easy.
I rented from Hertz on Sansovino--2 miles by taxi from the Florence train station . They gave me easy instructions to avoid the ZTLs. City rentals are cheaper than airport rentals just about everywhere. You can turn the car in at any Hertz in any Italian city or airport usually with no additional charges. Another popular Hertz turn in location is Orvieto because it is just 70 minutes on a local train to Rome Termini.
Where are you coming from?
If you are in Florence before renting the car, it would make no sense to go to Pisa or Orvieto to pick up the car.
We picked up in Orvieto and turned in at the Pisa Airport. Both were easy for us.
Tuscany is a large region, where do you plan on visiting?
I'm with Kyla: Pisa airport and Orvieto and very convenient. Orvieto is especially so if you go with Hertz.
The issue still is where the OP is coming from and where s/he is going to afterwards.
If the OP is coming from Milan or Venice to Florence, then after a couple of days in Florence, needs a car to go to the Chianti, does it make any sense to go to Pisa to pick up his car?
I DON'T THINK SO.
If after visiting Tuscany by car, the OP is flying home from Florence, or Bologna, or Milan, would it make any sense to go all the way to Orvieto to drop the car off?
I DON'T THINK SO.
Don't forget to obtain the compulsory International Driver's Permit for each driver listed on the rental form. These are easily obtained at any AAA office for a small fee and are valid for one year. They must be used in conjunction with your home D.L. so you'll have to bring that too. There was a post on the forum recently from someone who wasn't able to rent a car without an IDP.
You'll also have to be vigilant to avoid the dreaded Zona Traffico Limitato (limited traffic) areas, as hefty fines will result for each pass through one. Do NOT drive in Florence, as the city is just about saturated with automated ZTL cameras.