Drivers/Tours on Amalfi Coast, and Where to Stay Near Pompeii/Herculaneum/Vesuvius?

the driving around there can be notoriously treacherous.

The driving is really not that bad. Road is much better than "The Road to Hana", but has LA rush hour like traffic Creep and crawl for long stretches. By late Oct that may not be so bad. The problem with driving is where to park when you get to a destination on the AC. Having a hotel with parking solves only part of your problem

To get to Pompeii etc, staying in Sorrrento provides easy access.

Mid October will be busy, but not jam packed as it is earlier in the summer. Easiest would be to pick up your car at either Napoli Centrale or at Naples Capodicino airport about 4 miles from the train station, taking the Alibus to the airport.
Only takes 15 minutes and puts you about a mile from the autostrada. I don't think you'll have any problem parking, but it will still be expensive.

The other option is to use the busses and ferries.

https://www.positano.com/en/c/cantina-del-vesuvio-2/i/SM6R5

For decent low cost tours, check this out.

https://www.sharedtours.com

Naples is not “chaos!”

If you are flying out of Rome, I advise you to spend your last night there. You need to be at the airport about 3 hours before flight time, and you should allow about an hour to get to FCO, maybe only 1/2 hour if you will be traveling early early morning by taxi. If you have an afternoon flight, you could stay in Naples and take a fast train to Termini and then the Leonardo Express to the airport (allow 2 hours plus time to get to the Naples train station), but I wouldn't advise staying anywhere south of there. There are just too many ways you could be delayed and miss your flight.

I spent a couple days driving on the Amalfi Coast last year in February [I stayed in Salerno] when there were few tourists and very little traffic. While I didn't get stuck in the traffic jams Joe described and which are likely in October, I did find it challenging to find parking in some towns. Expect to sit and wait for long periods of time in the small parking lots in the AC towns waiting for someone to pull out.

The road itself - well, with a very few exceptions, it's a narrow, two-lane road without shoulders, hugging the rugged coastline. There are ups and downs and sharp, blind curves. Where there are shoulders, there are usually parked cars. Listen for the bus horns. They blow them before every curve to alert oncoming traffic. When a bus comes around a curve it takes up most of the road. When 2 buses meet, a not uncommon occurrence, one may have to back up to allow the other to pass. That means that ALL the cars behind it have to back up too.

I also spent 5 nights in Naples and I agree with Suki. There's nothing wrong with staying there. Sorrento is a charming town and you can use the Circumvesuviana commuter train to get to Pompeii and Herculaneum, and also Naples. The ruins are closer to Naples however.

-not super expensive car and driver
This is a high-tourism area, and a relatively high cost one. While you are traveling in shoulder season, rates are set by the invisible hand of the market. You don't negotiate or choose a rate. Because you're in smaller towns, you may have more flexibility, or you may find fewer drivers in the market. Your B&B will know the names of reliable people.

As others have noted, parking beyond your B&B is a major issue. There are not many free spaces in the towns you'll want to visit. When we were in a hotel in Sorrento (late May) we saw a long line of cars every evening, inching up to the gate for an underground parking lot. When we hired a car and driver for 8 hours from Sorrento (240 Euros), our driver tended to park with friends in pay lots and play cards during our "free time" in Positano, Amalfi, and Ravello. You can get to those town on the SITA bus, which sometimes has lines to board, especially in Positano and Amalfi.

Most people who want good daytrip connections stay in Sorrento, which is attractive but touristy. It also has far more ferries (seasonal schedules need to be downloaded - watch the dates) than, say, Positano or Amalfi. But I think you're asking about a smaller town closer to Naples. The point is that your primary need is to be in a town on the Circumvesuviana train line (which has multiple branches, but most posters here stay on the Sorrento-Naples line.) If you use the Search box top center, you might find the very few posts here that talk about Massa Lubrense, Vico Equense, and other towns. Nobody needs to stay beside Pompeii to go there. People sleeping in Naples and in Sorrento go to Pompeii by the thousands, on fast, efficient daytrips.

If you have a car, you have the option of driving to Pompeii from the two AC towns you're sleeping in. You may tire of the pebble beach that's distant from your B&B, or the water may be too cold, or it may be a grey day when you need an excursion. You are right to avoid driving in Naples.

Edit: My sister's family stayed in some sort of luxury hotel near or in Sant' Agata sui dui Golfi, but I don't know the same. I have to warn you that there are a lot of group-tour hotels between Sant' Agata and Sorrento, that you don't want. Sant' Agata is quiet and attractive, but not, for me, a three-night stay. And it has no beach, and is far from the Sorrento ferry dock.

Note that there attractions you haven't listed, like the royal palace at Caserta, and I had a faint (and unrequited) desire to see the Cave of the Cumaean Sybill. Will you walk the Path of the Gods?

It's not at all a fair comparison, but there's a scrap of truth in saying that the Gulf of Naples is like Cape Cod, MA or Sarasota FL. It's attractive in spite of its touristy status. You may have an unreasonable hope of finding an unspoiled rural village where grandmothers in black carry dinner to their daughters in law in the evening, with a beach and a Michelin restaurant! Wait till you see the only beach in Sorrento- a real disappointment, but at least it has imported sand.

Thanks so much for the replies so far. We really appreciate all suggestions, and the different pieces of data are really helpful so far. We welcome more. Since we are going to be spending 10 days down on the Sorrentine Peninsula, I had thought it might be nice to spend the last couple of nights somewhere up closer to Naples but not in it.

I also didn't mean to imply that Naples was chaotic in a bad way, so I changed the word to frenetic, which I also mean in the spirit of being fast and energetic, not in any judgmentally negative sense. I love the exuberance of Italy, which is why we are spending a good amount of time there again this year. I am, however, a light sleeper so I am trying to avoid lodging in locations where there could be a lot of late-night activity around us. Mille grazie!

We've used Aldo Limos and are booked with them again next month. https://www.aldolimos.com/