You must first analyse the type of driver you are. If you are not sort of Type A, have not driven on various types of terrain or in large cities, you may want to rethink driving. Having said that, it's the BEST way to go IMO!
My dh and I drove to Civitaveccia in sort of a round about way, going from Como to Bellagio, onto a short ferry ride to the southest side of that peninsula, on to Venice for a few nights, then to Siena for one night, then on to Civitaveccia, which stops in the cities mentioned above. It was a WONDERFUL experience! The scenery along the autostrada is lovely heading south through central Italy, and you can exit to make visits to some hill towns here and there if you like.
Depending upon where you will be driving in from, just be prepared to stay very alert. Italian drivers know exactly how wide their cars are - to the inch! ! Pull over to let faster drivers pass (and there will be faster drivers!). It's not like here in the U.S., where people sometimes will purposely stay in the "fast lane" because they want you to stick to the speed limit. If you do sightseeing along the way, there may be very narrow, curving roads and hills. You quickly learn to just stay put and let the car facing you come in most cases. However, if you have to drive inside a large city such as Rome, you sometimes have to be aggressive! I wouldn't recommend driving in large cities, except maybe from your hotel to get OUT of one. For instance, we drove to Venice and parked our car there for 2 days and nights in a huge garage, taking a vaporetto to our hotel. (You can't miss where to go to park when you are heading into that city!)
We used AutoEurope and I will sing their praises. Everything was included in our price. After our cruise, we picked up a car again in Civitaveccia and took it to Pompeii, Positano and eventually to Portofino and Milan. While staying at a hotel in Positano, we had to turn our car over to the nephew of the inn where we stayed to park inside their tiny, very tight, garage. The next day we were taking the car out to ride down the coast a bit when my dh noticed the mirror had been badly damaged and almost torn off! It HAD to have been the nephew, and the inn accepted responsibility. We told them we would see if we were charged for the damage and contact them if we were. AutoEurope's agency in Milan didn't blink an eye and didn't charge us a thing! NO PROBLEM!
The ONLY PROBLEM w/had was finding the rental car office in Civitaveccia! (This was 7 yrs. ago, before GPS was popular.) Some major brands are right along the main blvd. along the promenade in front of the entrance to the port. But this one was up some steps, on a sidewalk-like area up above a main st. that lead down to the waterfront area. Besides that, their office was closed! It was a Saturday around 12:30 or so. Hertz (or Avis?) told us it was just closed for the afternoon siesta time. However, no one came back by late afternoon. Someone we dealt w/during checkin on our ship just HAPPENED to be related to the girl working at that rental office and called her on her cell phone. The girl had gone to ROME to visit an aunt and would not be back that day! She said she didn't realize anyone would be turning a car in that afternoon. (Though I think otherwise!) HER relative was a young man at the Hertz (?) office. We were instructed to take the car and keys to him and park it outside, right on the street! We had no choice as our ship was about ready to depart. I immediately emailed AutoEurope from the ship once we were at sea. Everything worked out fine, but for a couple of hrs. we were beside ourselves with what to do w/that car! Just make certain you get GOOD directions to the drop off location (there was no car lot by the rental car office, which was also sort of puzzling, and people we asked mostly spoke very little to no English so trying to explain the very unexpected and odd location was not easy). Also, it probably wouldn't hurt to reconfirm the rental and approx. time you will be returning it.
MIBCRUISER gave you a great reply. We would concur. The only difference is that we had damage to the car and the rental car company put $500 against our credit card. Just make sure you got full coverage on the car.
I want to add sort of an addendum here, after an experience in Sintra, Portugal this past June. Previously, my husband would NEVER bother to get an int'l. driver's license on our trips. We have never really had to have one before, as he always pointed out, even when the guidebooks and online travel blogs said to get one. So I read a few things on one website about accidents in Portugal and urged him to get one. He had to go p/up something for me at a AAA office prior to our trip. While there he actually got the int'l. license! Guess what. While in Sintra, he parked on a side street right in front of the door to a B&B, against my advisement. There was no sign, but I had a "feeling" this was not a good idea or someone else would have already parked there. When we returned to our car, there were 2 motorcycle cops standing there waiting. One was on the phone calling a tow co! At first the "ticket" was going to cost 90 euros! I registered shock at the cost for just a parking ticket, meanwhile trying to be very respectful and trying to make sure my DH did the same and didn't "lose it". In the end, the "head cop" decided to reduce the charge, and he leafed through a booklet to find out some other charge's code else to write down, lowering our cost in the end to what amounted to 25 euros - and we felt LUCKY by that point - ! Had my husband not had the driver's license, that would have been another charge. It's mainly only for translation purposes so the police are able to translate the info. on American (or whatever) driver's licenses - or so I've been told. While I did do a LITTLE driving, I did not get the license. Maybe next time I will - just in case!
We did have damage to our car our first time driving in Italy. We stayed at a great place in Positano that had parking beneath the hotel. The owner's grandson - or nephew (?) - parked all the cars in that oh, so tiny garage! He was a pretty young kid (looked about 14 maybe?), plus really had to squeeze them all in. Then our last day there we noticed that the mirror had been pretty well just ripped off! It was not like that when we had last driven it. The hotel's owner was great and said that if our insurance did not cover it to let them know and they would. We had rented from AutoEurope and had full coverage through them. I THINK it was required then (about 8 or 9 yrs. ago) - ? We turned the car over at Malpensa Airport w/out any sort of hitch at all! We have since sometimes relied on coverage that is provided automatically through the credit card that we use to rent the car with. I always call and get the low down on exactly what we should do in case of an accident or damage. If something happens and we do not follow their instructions, get the proper documentation, etc., we could end up not being covered. Sometimes we have found ins. automatically comes w/the rentals in some places, or at other times we have taken it out simply because we didn't want to take the chance of having to possibly jump through hoops IF anything happened. (Since we mostly travel on a pretty tight budget, there are times we just hope for the best and rely on the credit card's ins. )
The only time we have actually had to USE our credit card's ins., however, was once in Ft. Lauderdale, FL, when my husband crushed a section of a minivan's rear end backing into a short parking guard pole in our hotel's lot. I had my husband call our credit card co. as an afterthought the next morning, as I wasn't totally sure about the benefits of the card but thought we MIGHT be covered. Luckily, we were!
You sound like a pretty savvy traveler, but thought some people might not realize they could have coverage through their credit card.