Italy in Sept./Oct for 16 days on ground in Italy: Florence/Tuscan Hillside and AC questions

RE Positano vs Sorrento. If you can work it to visit Pompeii en route (storing luggage), then you could stay in Positano. For some, the scenic village experience is the whole reason to go and Positano epitomizes that. If you are fine with a still-scenic but larger base more convenient for all day trips from one place, choose Sorrento.

I would stay in Florence for the 2 nights and skip renting the car altogether. There are many great towns you can explore by train. With only 3 nights to explore Tuscany I would travel from Florence to Siena and base there. From there you can take a day trip to a variety of places, Arrezo, Montepulciano, etc. You can then train onto Rome/Amalfi coast. I don't have any real good experience about basing out of either Positano or Sorrento. I'm sure others can better suggest either or another option. Enjoy.

Where would you be able pick up/drop off the car? Specifically in Florence? If at airport that seems a pain- out of the way for both pick up and drop off. Assuming you are taking train from Venice to Florence?
You might do some cost analysis and see if renting on your own thru AutoEurope doesn't give you better options.
You will not want or need a car in Florence at all.

We did 3 nights Florence then picked up car and went to Siena 2 nights then Montepulciano 2 nights. (Then Assisi for 2)
I was very careful to pick hotels with easy access and parking at those locations so we didn't worry about ZTLs etc. PM me if you'd like the names of those hotels.
We liked Siena well enough but 2 nights there was enough for us. We absolutely loved Monteplulcinao - from there we visited Montalcino, Pienza, Bagno Vignoni, San Quirico, etc

We love being in a town in the evening and the mornings before tourists have arrived so I would want to stay in a hill town and as well as in a city (Florence).

Amalfi Coast- we are going next month so no first hand experience yet- but we decided to do Sorrento 4 nights then move to Amalfi for 3. From Sorrento we will visit Capri, Pompeii and probably Naples. From Amalfi we will visit Positano, Ravello. Amalfi has better connections and was a bit cheaper as well as a bit flatter/less touristy.
Sorrento seems like a better base for all the Amalfi sights but you might consider doing 2 there then 2 in Positano or Amalfi? Figure out your transportation time/costs to get back to Rome.
From Amalfi you can take a ferry or bus to Salerno then direct train to Rome. From Positano it's a bit more work/transfers. From Sorrento it's fairly easy. (Circumvesuviana to Naples then train to Rome)

If we base in Sorrento, I agree a visit to Pompeii on way to AC would be best but I would need to find out where we can store our luggage.

From my research, it seems there are benefits to driving through the Tuscany Hillside rather than train travel because of possible delays and losing valuable time.

We would not drive anywhere in Florence except on our way out picking up our rental car which would be at the Florence via di Santa Lucca station (which I believe is the train station) We would only use the rental car for three days during our travels on the way to our accommodation. Wherever that may be...

I suggest staying in an apartment just outside Florence for all 5 nights. One location that comes to mind is Galluzzo, which is just south of the city center and well connected by bus. It's a very pleasant area with a nice Esselunga super market (excellent selection and prices). The #11 bus runs from early until late and drops you off right in the city center. Parts of Galluzzo are on another bus line that has shorter hours, but the walk from the #11 bus stop wouldn't be terribly long as long as you're within the "town." It's also easy to get from Galluzzo to the roads to the places you want to visit by car in Tuscany, and it's an easy drive from the place you plan to pick up the car. A spot check of VRBO for the last week of September shows a nice apartment 2 short blocks from the #11 bus line with patio and parking for $89 per night.

Thank you Frank. I'll check that out.

For Tuscany, I would do 2 nights in Florence and 3 nights in the Val d"Orcia, near Pienza. I would have a car for the Tuscany hill towns. You need to decide if you want to be on a agriturismo versus in a small town.

For the Amalfi Coast, it is a repeat destination for my family. Honestly, if you are not opposed to relocating, I would split your time between Positano and Capri. Check capri.net for ferry schedule and hiking possibilities.

We stayed in the Villa: http://www.ilcellese.it/en/ with a rental car and toured all the little villages in Tuscany. It's a short drive to Florence and we parked at the train station then walked around the city. It's not worth more than a day; very small & overridden with tourists. The small villages are much more delightful! We then drove to a rental place in Positano (it's very central the to the coast) and left the car there and hired a driver to tour the Amalfi Coast. We then drove to the Rome outskirts to drop the car off then took a taxi to our rental in Rome. You really need a GPS to get to the small villages.
October is a better month; less heat & crowds.
Jean

If we base in Sorrento, I agree a visit to Pompeii on way to AC would
be best but I would need to find out where we can store our luggage.

Sue, you can store luggage right at the scavi or at the train station (Pompei Scavi-Villa dei Misteri).

We also visited Pompeii on our way to the Amalfi Coast (stayed in Pompeii one night so we could tour in the morning as soon as they opened). With four nights in Positano we were able to spend one day in Ravello (a very long day that included an evening concert), one day in Amalfi, and one day in Capri. We saw Positano itself in the late afternoons/evenings after our touring. This worked well for us.

We spent a week in Greve in Chianti. We had been to Florence before, so we took an early bus from Greve and arrived in time for our 8:30 Walks of Italy tour. We took a late bus back to Greve after a wonderful day.

Since it is your first trip, I’d suggest two days in Florence, then pick up the rental car and stay in an agriturismo either near Greve or Siena.

Driving in Italy is not hard, but you need to study up on signage, especially ZTLs, which are well marked. Don’t speed, there are automatic cameras. I came home ticket free.

Have a great trip, you are going to love Italy!

Hi Sue, for your time in Tuscany, I would recommend staying in the center of Florence for 2-3 nights and then in a small town for the remaining nights. The small villages are so charming at night and taking a morning walk after breakfast. Being in the center of town will maximize your time in Florence, and it’s nice to be able to have the option to stop in your room for a little break, too.

If you’re interested in taking a wine tour, etc. check out wine tours from Siena, etc. If driving, know the alcohol limit which is stricter than the US. People have mentioned the ZTL; search on that word in this forum for some drivers who received $$$ fines months after their trip. (I should have noted it in Euros!).

There are so many wonderful Tuscan villages! I have only been to Montepulciano, Pienza, San Giamagno and similar besides staying at the larger Siena, Arezzo, Lucca, etc., and we just travel by train and the occasional bus. You will have a fantastic time regardless of the town you select!

Florence: Great Hotel: https://www.loggiatodeiservitihotel.it

Agrotourismos in the hills to the southwest of Florence are great fun - there are many, but they may be an hour drive each way to any of the sites like Volterra.

Fattoria Barbialla Nuova (rustic) https://www.barbialla.it

Casa Montecucco: http://casamontecucco.com/

Of course there are agrotourismos southeast of Florence towards Montepulciano too.

One can reach reach the southern hill towns like Volterra, San Gimignano, Montepulciano, etc from Siena too within an hours drive. The next time we go we have already definitely decided to try at least one night in Siena.

Florence south to Naples/Pompeii/Herculaneum is about 5 hours on the train but is easy from Florence, the other towns you mentioned are a bit further. https://www.trenitalia.com