Originally Posted by mreynolds767

Have used US based Chase CSP as my insurance coverage for Italy many times ; just make sure to decline any possible options otherwise you will void Chase's coverage. In Italy a certain level of coverage is mandatory just make sure it is the minimum allowed and be prepared for a decent size hold to go against the card (500 - 1000 euro depending on the car you get).

Have dropped off a rental at NAP airport a couple of times and that is easy driving, right off the highway. Not sure how drop off is at the train station in comparison ; as a general rule you absolutely want to avoid driving in Naples. Far worse than driving in Rome which is also to be avoided and has tricky ZTL zones anyway. Knowing this is easy I would drop the car off at the airport and than take a taxi to your Naples area lodging. You will need to drop off your luggage before you take a train to Pompeii any I assume. No reason to stay in Pompeii.
No need for a car in the Naples area but yes it will be a HUGE convenience for the first part of your trip.

Other than the ZTL areas driving in Italy is usually quite painless. Map out any stops you plan on making, ZTL's are a given in the larger cities but even small walled towns will have them. Knowing and navigating to parking lots outside of the ZTL is something you can do pre-trip and that makes things much less stressful.

Car size is a little tricky as a larger car you will not want for any small town driving but is helpful to have the power for significant hills and for traveling at highway speeds BUT most importantly is it is nice to have enough room to fit and completely conceal your luggage when traveling. In Italy you should not leave a car with any luggage or valuables showing at any time ; so if the car rental is not large enough to conceal all of your belongings than do not make any stops when in route from lodging to lodging other than gas of course. In general the cars are smaller and less power than US versions of similar car types.

Oh one last tip. Though may do not do this ; a IDP is required for driving in Italy. You as a US driver's license holder will need to visit a AAA office and they can prepare one for you for about $25. Is only valid for 1 year so a bit of a pain and I never been asked to show it. BUT if you were to get stopped by the police or in an accident and you did not have one you would be in big trouble.