First time/thinking about renting a car

My wife and I rented a car for 12 out of 30 days for our first time in Italy this past May and had no problems. There should be no problem returning the car to a different airport in Italy. The big charge would be returning it in a different country. The horror stories about huge charges after you get home come from wandering into a ZTL (limited traffic zone) that many towns/cities have. They photograph the car and send you a ticket months later. Just have to be careful. Having your own car gives you the freedom to wander where you desire.

Several years ago we rented a car for our Italian trip. Drove from Rome to Florence to Venice to Milano. Here's the thing about driving in Italy, it's not for the faint-hearted. Are you used to driving in Chicago or Boston or NYC? Or in New England for that matter? If so, you'll feel right at home. Otherwise, it will give you an ulcer. Roads are well-marked and maintained, the autostradas are easy to use, but gas is expensive and parking is difficult and very expensive. What you gain, as you note, is flexibility to go where you want, when you want, stop and go, turn left turn right. But there's a price to pay.

Another option would be to rent car/driver when you need to go somewhere.

IMO it would help someone driving in Italy for the first time to be aware that driving there will be different than driving here. Parking will be more difficult and there are zones in cities where you should not drive called ZTL's.
But there are some areas of Italy that are not efficiently served by rail, and for those a car is worth the hassle.

Unless you're going to be using the car in a big city with ZTL's the drive should be wonderful. (Don't drive Amalfi Coast, however) ZTLs are almost the entire city of Florence and Rome IMHO. Just google map the cities/towns you want to see, or even ask the car rental agency regarding ZTLs in the cities you're visiting..

We've rented cars in France and Spain, and will rent one next time in Sicily, for the exact reasons you state. We've actually enjoyed the driving and also loaded the maps onto our Garmin before we left. I understand TomTom is more reliable in Sicily for some reason.

Ask the rental company about receiving the car at Malpensa and returning to Linate. Then figure in the price of two bus tickets, add in the inconvenience and make your decision.

Haven't been to Italy as much as you, but of the times we've been, we often rented a car for part of the trip. Our most recent visit, in December 2012/January 2013 involved lots of small towns with extremely narrow streets and tight parking places. We're glad we went with the smallest car possible that would carry us and allow us to stash our luggage out of sight (in the trunk or under the hatchback panel).

We picked up our car in Palermo and dropped it off in Sorrento, no problem, no extra charges. Just make sure your rental company confirms whether they charge extra and/or don't permit turning the car in at a different location. BTW, picking up a car at an airport or train station often incurs an extra fee, so you might get a cheaper price by picking up "downtown," but that may not be nearly as convenient. We've managed to avoid accidents and parking tickets (so far), and navigated by a Michelin Italy road atlas & maps in guidebooks or provided by the rental company - haven't needed GPS where we went.

Also, Italy is one of those countries requiring an International Driver's Permit (available at your local AAA even if you're not a member), so if you get pulled over or a cop wants to see your IDP, you'll need it or face a big fine. You'll need a passport-sized photo and about $15. AAA can take your photo but that was a big hassle for me with the camera & flash they used at my local office.

Last, getting gas (benzina) or diesel (gasolio) is generally no problem, and you can pay the station attendant in cash or with a credit card. After-hours, some stations have self-serve pumps that may or may not take an American-style swipe & sign credit card. If you have a chip & PIN credit card, that would work 24/7.

Yes, driving in Italy is different from the U.S.; but it's been getting less challenging lately because, I believe, of the enforcement of speed limits by automated cameras. (Don't let yourself get caught by one.) Also, don't be intimidated by the honking that Italian drivers seem to love to do. They won't pull a gun on you. We've been to Italy 15 times, and have had a car for at least part of every trip. We almost always return it somewhere different from where we got it, and we've never paid a drop fee. There is a thread on this site about driving in Europe. You'll find lots of details and advice there.

We find renting a car the best way to see the countryside, and we'll rent a car when leaving the bigger cities. The rental agency will give you directions to avoid any ZTL's.

I received a $40 bill from Hertz for a service charge that stumped me. Later, I received a certified letter from the City of Venice demanding $140 in Euros to be wire transferred into their checking account. It was then I realized that they got me on one of the automated cameras on the causeway going over to Venice--less than 2 mph over the speed limit. The $40 Hertz charge was for their time and trouble telling the Venice police who had that car and where they lived. You just have to be careful driving around the larger cities.

Most of our driving was in small cities and off the beaten path places--well worth driving to.

We never pickup rental cars at airports, as most of the time there are huge taxes/charges. City locations will just about always be cheaper. And most Italian car rentals can be returned within Italy without any up charges. They'll eat you alive if you want to return the car in Switzerland or Austria, however. And physical damage insurance will be mandatory in Italy, but the rates are far less than they charge in North America for the same coverage.

Advice: I just recently learned that if you exceed the speed limit on the freeways in Italy, even if you're not seen/radar, etc., you can receive a speeding ticket when you arrive at the next toll booth -- because they know the times you should take doing the speed limit!! LOL. So if you arrive at your destination sooner than you should, you were speeding. LOL!!!

I would STILL (and do) rent a car for the small villages as you describe on your itinerary.

Quit listening to all of us, and just rent the damned car. Get your International Drivers Permit (required) from your local AAA office and get the insurance when you rent the car (required) , follow the rules and you will have a blessedly GREAT time in Italy!

Dorothy you won't be in Kansas any more, but that's the whole point of traveling!

We have been to Italy three times and have rented a car for portions of each trip. Places we didn't drive in Rome and Florence. Traveling between cities and towns is very easy. The garmin nuvi is great. I used mine for Italy and France and it has never let me down. Just know that driving near the coast and lakes can be a bit nerve racking the first day or two. The roads are small and the Italian drivers love to tail gate. When they did that i would just pull over when I had the chance and let them pass. Bring lots of Euros for parking meters. Parking is a pain but I always eventually got a spot. But you always pay for two things in Italy, for parking and bathrooms. Get an International license, which is easy to at places like Triple A. But you also need to have your American license. Make sure you know which car you are getting. Lots of manual transmissions there so make sure you get an automatic. Also make sure you request a specific class or size of a car. We never liked tiny ones or big ones. Never got the one we ordered but always got the car in the class we ordered. Check to see if it is regular or diesel. We never paid a whole lot more to drop off in another city unless it was in another country. good luck

The fear of driving in Italy is like the fear of flying. Largely unjustified.

Myths steeped in hogwash induce anxiety.

Here's another one:
Leave a local newspaper in the back window so thieves will think you're a wise native out for the day in his own car. Never mind the rental agency stickers and barcode decals since nobody would notice them.

A car's a car. A road's a road. Italy has both and they work the same as every place else.

Im also going to be road-tripping in May, so I am taking notes here as well :)