Florence ZTL - Safe to pick up inside ZTL (Hertz) and return at Florence Airport

Option 1 is at moment unfeasible as the bridge over the river is closed for maintenance.

As for option 2, remember that within city borders you are limited to 50 km/h speed. There is a speed radar just after piazza Ciampi that is the most profitable device belonging to the city administration.

I suggest to return the car at the Sansovino location that is just in front of a tram stop and probably more convenient than the airport.

Almost all toll roads, but a few in the very north of the country, have barriers when you enter and when you exit. As you enter you take a ticket, when you exit you hand the ticket and pay your toll.

Thank you lachera. Any warnings about picking up car at Borgo Ognissanti? Do I need to worry about ZTL if I’m already inside and leaving. I already have reservation that is paid for. I can change drop off location for small fee. Thanks for speeding warning. Is Waze app good within Florence and ZTL?

Why not just pick up and drop off at Sansovino?
No worries about ZTLs at all

It’s just a short cab ride from the center

We took a cab from the train station over to Hertz's Sansovino location--maybe 2 miles.
They gave us directions how to get south of Florence without getting anywhere near the dreaded ZTL.
We were staying outside of Certaldo--close to San Gimignano--in an agriturismo. We shopped at the big grocery stores in Poggibonsi--5 miles south. It was a great location to ramble from town to town--including getting over to Volterra.

The only thing to care when leaving Borgo Ognissanti area is that in via della Scala between via Rucellai and Porta a Prato, the right lane is for taxies and buses only.

When you exit the Garage Europa on Borgo Ognissanti turn right (right turn only). Go straight about 100m then turn right at the stop sign onto Via Rucellai. Drive via Rucellai to the end (church in front), then left turn only at the stop light. You are now on Via della Scala. Stay in the left lane (right lane is bus only). At the end of Via della Scala there is a stop light (intersection with Viale Rosselli). Turn left and follow directions to Autostrade (green signs).

If you are scared to return at the same location then via del Sansovino or Via Ambrosoli (Hertz Firenze Sud) are better than the airport.

You all are awesome. Thanks so much!

You can also get to/from the Sansovino rental car location using the T1 tram. There's a stop practically in front. Just another option.

Another vote for the via Sansovino location. We just returned our own car there a couple of weeks ago and were pleased with the location and service. We particularly wanted to avoid the congestion near the airport and Sansovino fit the bill for us.
One other thought: there's a Hertz location just a couple of blocks from the train station in Siena. Might consider taking the train down there to collect your car rather than dealing with the hassle in Florence. There's cheap parking at the train station too - 2 Euros per day, and it's about 45 minutes to San Gimignano from there.

I don’t recommend to pickup your car in Siena to go to San Gimignano.
That would be backtracking big time. San Gimignano is half way between Florence and Siena.

Roberto is correct of course. It wouldn't make sense to make a separate trip to Siena just to pick up the car.
What I meant to say was that if the OP's travels were going to include more of Tuscany anyway, including perhaps a day or two in Siena as part of their itinerary, picking up the car there might be a workable alternative to Florence.

Yeah, the plan is to go directly to San Gimignano from Florence, so we would need to pick up the car from Florence.