Cost and stress of renting a car from Florence to San gimagnamo

I wouldn't rent a car since you can get there by public transportation.

My daughter and I did a one day car rental in December 2018. We picked a Fiat Arbath in downtown Florence early in the morning and returned early evening. The most difficult part was navigating out of Florence, but using GPS it was doable. Our first stop was SG. We spent about 3 hours there and enjoyed a quiet morning before the tour busses arrived. The view from the bell tower, main church was beautiful. Sienna was our next stop. Parking was tricky and we had a bit of a walk to the center of town, Sienna was well worth an afternoon visit. You will have more daylight than we did in December. I travel often and use a combination of public transportation, hired drivers and occasional, single day car rentals. Once out of Florence, the roads are fun to drive and spectacular views.

I like driving in Italy and have driven in Florence several times. It IS stressful but I've stayed out of the ZTL. I've picked up a rental near the train station, and they gave me decent directions to get out of the city. (I think returning a car that deep into the centro might be more difficult.)

In October I need to pick up a car in Florence to go near SG for most of a week before flying out of Milan. I've decided the easiest option is to pick up and return the car at the airport. There's now a tram from train station to airport that runs frequently. I'm arriving by train and can take the train to Milan. I know I'm incurring some kind of surcharge by renting at the airport, but easier is better than cheaper sometimes.

I'm needing a car for six days, which is completely different than a day trip, but this might give you more options to consider.

If you simply want to see San Gimignano, taking the bus or train to Poggibonsi, then the bus to San Gimignano, is probably faster once you consider the rental paperwork process (amd sometimes the long queues at the rents offices), plus the car drive and rental return process. If you decide to roam around the countryside, for example the Chianti area, or want to visit other towns besides San Gimignano, like Monteriggioni, or the Chianti towns, or Colle Val D’Elsa or all of the above, then a rental would be better.

Thanks for the input and suggestions! We’ll do a tour! You all are the best! Thanks

hire a car and driver for the day, your hotel will know someone. the stress and agg is not worth it.

And FWIW, driving in Italy is NOTHING like driving in LA. More like driving on the East Coast, if you're good with that.