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i hope your itinerary is not as complicated and in the order of your original post. You're landing in Rome, in the middle of the country, then south to naples, then way north past rome to Florence, then Nice France, then Milan, verona and Venice.
that's the only part of the trip that makes sense.
When I went in 15 I landed in milan, then trained to Verona, venice, Bologna, then on to Luccca, and from there Florence, Orvietto and Rome. And it took us a month. I hope you're planning longer than that.
We used trains exclusively because connections were good and didn't plan on going into the country. But, to each his own.
The problem with the suggestions of renting cars and then dropping them off and then getting trains and then renting again is that it can take much longer to collect and return rental cars in Italy than in the US.
We always rent cars in Italy and one trip we had a car from Milan to Padua, then a car in Sardinia and another in Sicily. Last year we had one to and from Milan and it was a nice long queue to pick it up, over an hour. Before returning the car we tried to fill it up with fuel and had a great battle trying to find anywhere. Eventually a whole crowd of us tourists from three different countries were clustered around the self-serve bowser trying to work out how to get it to work and how to pay. I do not know how you would manage without a chip and pin credit card.
What we do is book somewhere to stay with free parking and use alternative transport if need be. The exception was Rome, where we only collected one on the day we were moving on from Rome. Collecting our luggage from the hotel resulted in our fine six months later, which eventually we were not required to pay. (Long story!)
Our first trip to Italy lasted a month. These days we spend a couple of weeks only in the one region; last year in the area surrounding Turin. It is too crowded in Italy these days to try to fit in too many places. Especially as a lot of the country still close down for hours in the middle of the day and also many museums are closed at least one day a week.
Something that hasn’t been said yet is the level of comfort driving in a place with strange signs. Years ago my wife and I drove all around Provence and the Cote D’Azur, and I was comfortable as I speak and read French. Crossing over into Italy was more stressful as at the time I knew no Italian, so reading and mentally translating Autostrada signs while driving wasn’t fun.
Another driving hazard can be that the satnav directions can lead you astray. One notable time we proceeded up and up a mountain in Sicily (DH refuses to use common sense and insists on following every instruction) We ended up on a very narrow road and there was a cliff, with the road continuing at the top, about fifty feet above us. Luckily we were just able to turn around. I have to say I was slightly displeased!
Then there was the hire car which we discovered was lacking functional back seat seatbelts.
I suppose that how you will find the driving is influenced by what type of driving you do at home. We live in a very congested big city and in a country with a distinct lack of decent expressways. So the driving is not much of an issue overseas. Surprisingly perhaps, none of our friends seem bothered by driving on the other side of the road. Driving in the US and Canada is a breeze but we find it is worth it in Europe for the convenience. Last year in Europe we had a set a golf clubs with us and I cannot imagine managing them on trains.
We (wife, teenager, me) were just in Italy at the end of June. We spent 3 days in Rome without a car. We then went back to the Rome airport were we rented a car to go to Siena. We stayed 4 miles outside Siena. We spent 4 days in this location and drove the car all but 1 day when we took the train to Florence. We did drive to the Siena train station were there is cheap parking and took the train to Florence. Renting a car was no problem and it was not expensive. It is the only way to get around Tuscany.
We rented, from Hertz, a 2019 Audi A3 4 door hatch with an auto trans and a turbo diesel engine. This vehicle would work for you also (a VW Golf would have worked also). We each had 1 wheeled carry on and a backpack and we could have easily fit another person and luggage in the A3. There are tons of automatic transmission choices these days due to the popularity of dual clutch paddle shifters that do not use a clutch pedal - they are completely automatic. The mileage with the diesel was impressive (43 mpg, including some 145kph runs on the major Autostradas). The tolls were reasonable and we were able to pay with a credit card at the toll booths. Driving in Italy was not difficult, you just have to be strict about what lane you are using on the highways. We did not drive in any cities other than getting to the Siena train station. The A3 came with a built in navigation that I was able to program in English. We also backed that up with google maps on my phone. We drove 1000km and only made a few wrong turns. There are many cars smaller than the A3, but the Audi was a good size and we never felt out of place or too big in it. It fit in very tight parking spaces that are common in Italy. There are plenty of A3s on the roads.
I would not hesitate to rent a car again in Italy. It can be an affordable option. The 5 day rental was about 150 euros plus diesel. The round trip train from Siena to Florence for the 3 of us cost 60 euros. We did not drive to Florence because of the parking logistics in Florence, but the trip would have been less expensive via car.
Do not drive in Florence. Restricted driving areas not marked well. 150 Euro fine, I know, I got the ticket from Enterprise about 2 months after coming back.
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