14 days Naples to Palermo?

I’d first work on deciding if you want to see Naples and its surrounding area and Palermo and its surrounding area. You can do those two areas fairly well (a week each), or you can skip through a whole lot of land without adequate time to see the places at either end. Either could be a great trip, but you definitely don’t want the car in Naples or Palermo.

You could split the 14 days between Naples, Palermo, and Trapani, with Palermo getting the lion's share. I spent 6 days in Palermo and was never bored. I made day trips to Cefalù, Agrigento, and Monreale from there. I visited Erice, Segesta, and Mazara del Vallo from Trapani.

Hi, Giangilberto from Milan, so the advice I can give you is to carefully evaluate some logistical aspects.
The first is: between Calabria and Sicily, there is the Strait of Messina, and you must necessarily do it by ferry.
Then there are some car rental companies that apply restrictions, and in some cases they even prohibit the rental car from taking a ferry, so you will have to check this with the car rental operator you want to use.
The act of taking the car on the ferry must be explicitly authorised by the car rental company in order to avoid possible penalties or even the cancellation of the insurance in the event of an accident. This means that you should always communicate with the car rental agency your intention to take the car on board and travel to Sicily.
There are companies that require a supplement for the maritime crossing and so on.
Then we have another aspect: strikes start again from September.
August is a protected period, while they start again from September, so you should check on the official website of the ministry of transport regarding strikes to see if there are any strikes that could affect your days and, above all, could affect any means of transport such as the ferry that you should take on those days. As other users of the forum have already mentioned, both Naples and Palermo have ZTL zones where the car goes from being a resource to becoming a problem, so in the cities I don't know if it makes much sense to have a car for everything else, for example Cilento and Calabria absolutely yes, especially in Calabria, where public transport is quite scarce.

This is all extremely valuable information. From this I see

Option 1. skip the car, travel Perugia to Naples by train, (?) days in Naples, Naples to Palermo (fly?), perhaps rent a car out of Palermo to explore Sicily. 6 days each in Naples and Palermo seems a little much (allows 2 days for travel), perhaps not. What is the best way to travel Naples-Palermo?

Option 2. Drive around east and south of Naples 3 or 4 days, ditch car outside Naples, 4 days each Naples and Palermo cities.

Option 3. Given that we want to spend time in Naples and Palermo, not sure there is a 3rd. option.

Is it easy to get from Palermo to Trapani?

Erice looks very interesting.

We've actually driven pretty much the route you are describing, but it was 25 years ago. We did Venice to Orvieto to Pompeii ruins to Enna in Sicily. Two one-night stops along the way (Brisighella, Scilla) and two nights each to visit Orvieto and Pompeii+Herculaneum. It is faster than taking the train. The ferry can be fun. Way better roadside food than along an American highway. Like you, we have done lots of driving trips in Italy and like to drive there. We used to drive from St. Paul to either New York or Washington DC several times a year, so driving the length of Italy seems quick and easy to us.

Your drive would be 4+ hours from Umbria to Naples, another 8+ hours to Palermo. So, you have about a dozen mystery days. I would spend them all in Sicily, assuming that one of your Naples days is visiting Pompeii. I would get off the ferry in Messina and drive clockwise around Sicily, ending with at least 4 nights in Palermo. Places we especially enjoyed in Sicily last spring (on our 2nd trip there) were Randazzo, Catania, Ortigia, Ragusa Ibla, Modica, Piazza Armerina to see the Villa Romana, Erice, and Monreale. In 2001, we enjoyed the ruins at Agrigento and going up on Etna (erupting then, erupting last spring, and erupting now!).

No idea where you'd park your car while in Naples, but someone will know. There are other threads here about giving up your car before you stay in Palermo, either at the airport or in town somewhere. We had a late afternoon flight out of Palermo last year and just drove 1.5 hours to the airport from Sciacca (we'd stayed in Palermo at the beginning of that trip rather than the end).

Palermo to Trapani by bus is very easy. Segesta Autolinee has half-hourly service from Palermo Centrale. About an hour and a half ride. Check websites for current schedules and prices.

Option 2. Drive around east and south of Naples 3 or 4 days, ditch car
outside Naples, 4 days each Naples and Palermo cities.

I like that plan, gives you ample time for the cities at each end, and some time for rural exploring by car. I loved the Cilento area but I only scratched the surface. Surely will be quiet in October.
While you could fill a week in Naples, I think you would only need that much if you wanted time for the islands or on the Amalfi coast, etc.

Figure out where you want to go and what you want to see, first. After that, look at car vs. train (vs. flying? … or ferry from Naples to Sicily?)

There is a lot to southern Italy and there is a lot to Sicily. 14 days is not a lot of time. In 2024, we spent close to 2 weeks in Sicily, mostly on the RS tour, about 12 days in Puglia (with a week of that by e-bike), then 3 days by car to Naples via the Cilento, and a final 4 nights based in Naples with day trips to Pompeii and to the island of Istria - a month all in all.

Where you absolutely don’t want a car: Naples. You can get a car or drop a car at the Naples airport, though the afternoon we drove from the Cilento to NAP was slower and slower as we approached NAP. The final 4km (2-1/2 miles) took a good hour.

Yet as someone already mentioned, the car was very useful - really necessary - for getting from Lecce to the Cilento via Matera and then getting around the Cilento before we headed up to Naples via Paestum.

Our current plan, after all this extremely valuable advice, is train Perugia to Naples, 4 days in Naples, flight to Palermo, 10 days on Sicily. I think that will give us a feel for both locations, and we can always come back for more next year

Hi Brain, since you've decided to fly from Napoli to Palermo, you don't have to worry about the possibly ferry problems with a rental car anymore, and so my advice is to rent a car e drive across Sicily.
In Sicily, public transport is kind of bad, andi If I were you I'll definitely rent a car.

Sounds great! I’m hoping to get to Calabria eventually…Italy never seems to run out of appealing areas to explore!

I’ve been to Italy many times even though I like Spain just as much. This trip we start with 2 weeks in Torino and Alba, a week in an Umbrian farmhouse, then 2 weeks Naples and Sicily to start filling in a couple blank spots. I’m sure we will be back.

Have you considered taking the overnight ferry from Naples to Palermo? That way you pick up a day since your hotel will be traveling while you sleep. It's really a nice way to travel; relaxing, beautiful views and really good value.

We had considered and rejected the idea of the ferry but after considering the EasyJet or Ryan air + Naples airport scene I think we are on the ferry track now.