Car Rental Options...

If you are going to Sorrento you should return the car in Sorrento. Sorrento has rental offices with the major companies. Check the price difference between keeping the car while in Sorrento and not using it (also factor in about 25€ a day for parking unless your accommodations have parking) versus returning the car then renting again 5 days later.

Advice well taken! Thanks! Parking is available where I am staying in Sorrento, but only for certain sized cars, and my rental might be too big for the space provided. Fingers crossed! Glad to hear Sorrento is well covered for rentals.

If renting a car in an Italian city, I would advise you to make sure you understand "ZTL", Traffic limited zones. Driving into one of these camera monitored zones can result in a big fine from the municipality, plus a big fee from the rental car company for turning you in.

Since you don't need a car in Sorrento, why not use public transportation to get there and to Naples airport. It looks like there is a tram from Florence airport into town, and there are trains at least once an hour to Naples. There is also a bus between Naples and Sorrento.

Good to know! The Villa in Sorrento where I am staying informed me as to how to go about driving and parking legally. I hadn't thought about dropping off the car in Sorrento after the second half of my trip then travel to Naples via public transportation. Certainly worth considering. Thanks!

You will need a car to visit Tuscany (except for Florence, of course).
I don't know where in Tuscany you plan to be, but if we assume you stay somewhere in the Siena Province, driving to Sorrento and returning the car in Sorrento is probably the best option. You could also return the car in Tuscany and proceed by train to Naples, then to Sorrento, however depending on the amount of luggage, and the number of people in the party, driving to Sorrento might be best. It's a long drive (about 5 hours plus pit stops) but it's almost all on a freeway, so not hard to do.

When doing your research, check with them on the surcharge for renting in one location and returning in another. Sometimes the surcharge can be substantial. You didn't mention your destination once you have stayed in Sorrento. Where are you planning to go after that?

ZTLs have been mentioned. If you do your homework ahead of time, you will be able to avoid them successfully. Assume anywhere within the walls of a hill town, such as San Gimignano is ZTL. Also, ZTLs are clearly marked. There's parking outside the ZTL. We spent a lovely week traveling all around Tuscany and had no problems. BTW, also strictly observe speed limits. They enforce by using cameras and while you may not see a policeman, that doesn't mean you are not being seen by automated systems.

Is your intent to see the countryside on the way to Sorrento or just looking to drive to keep the car? It is a long drive from Florence and would take two days if sightseeing is your goal. You can drive straight through, but it would be at least 8 hours with minimum stops and good traffic. If sightseeing is secondary, then I think you'd be better off returning the car in Florence and taking the train to Sorrento, then renting again after your stay there.

Why not pick up the car in Salerno once you're done in Sorrento and avoid the headache of driving on the Amalfi coast?

Highly appreciate all the informative suggestions. I definitely need a car in Tuscany - overnighting in Volterra and Montepulciano with plans for day trips as well. The problem I am running into is my car drop-off location. So far all car rentals made in Florence have me dropping it off at the Naples Airport and not Sorrento. Suggestions certainly welcomed!

It helps if you tell us where you have checked -- all the majors?
It's an easy direct bus from Naples airport to Sorrento if the schedule aligns, so it's not a huge deal to drop the car at NAP (or pick one up there, if you cannot find a suitable rental in Sorrento that allows for drop off at NAP -- for the second rental).

Just returned from Italy last month. Rented and returned at Fiumicino airport. Great price but only because of the particular travel membership I belong to. We used the car to explore the Val D'Orcia and Puglia, and the use of a car in these areas is the way to go.

Since the pandemic, surcharges when dropping off at a different location are crazy expensive, I guess due to supply shortages. Hiring private drivers has also gotten out of control due to price hikes. It forces one to carefully consider itineraries based on public transportation and careful use of a car rental.

I used to rent in Florence and drop off in Sorrento, but no longer due to the surcharge. Best wishes on the itinerary...

Rented a car at FCo, drove to Spello for two weeks then drove to Naples and dropped it off, spent a night.

It was much, much cheaper to book it this way and easier than schlepping baggage on and off trains. Then we took a ferry to Capri, another ferry Capri to Sorrento.

Good suggestions keep stacking up! Thanks! I'm leaning toward pickup at Florence Airport, touring Tuscany as planned, then rental drop-off at Naples Airport, and bus/train to Sorrento. Five days later car rental number 2 - Sorrento to Matera et.al, and eventual drop-off at Naples Airport for flight home.