re: Transportation within Italy

You will probably not get a lot of satisfaction using this method. Europeans are used to taking their wheeled luggage 3/4 of a mile (or more) from their hotel to a train station, even over cobbled roads. What you're going to find in many cases is going to be canceled Uber/Lyft rides, repeatedly. Nobody wants to drive the two of you a mile for six Euro. There's special color I'll add because of Romans/Sicilians, but you will absolutely get destroyed financially trying to book a private car between Rome Termini and a hotel near the Coliseum, for instance. It's 2 miles and a 20ish minute walk (downhill, on the way from Termini). If you find an Uber within the first five tries that is willing to drive you on that route, I owe you a beer. I can easily envision a private transpo company charging you more than 35 Euro for that trip. Remember, your reservation for that is keeping them booking a lucrative drive to the airport, or to Vesuvius, etc., for what amounts to not much profit.

Also, take note of Catholic "stuff" that occurs when you're going to be there. Services may not be available depending on if the Pope is in town, the military shuts down roads, etc.

Since you're going South to North, I suggest stopping at Nettuno American Cemetery if you're at all interested in history. Super beautiful, and very, very, well maintained. I never saw any groundskeepers there (or any employees to be honest,) but it was great. There were more than a few Italians there expressing gratitude with their elementary aged kids as well. It's also a seaside town, so the to be significant other can be amused by non war things at cafes and whatnot.

(The rest that follows is sort of off topic, but EU transit advice.)

Be aware that at least in England (as of April) it's a pain in the arse to get a physical ticket on a train. It's all QR codes/Apple wallet, etc., so your number one job is to keep everyone's phones charged. ABC = Always be charging.

0. When you book a train, RESERVE SPECIFIC SEATS.

1. The train route you take between two points can vary. You can book a non-express train and spend eight hours going somewhere that could have take 3 hours if you'd booked the right train (between the same two cities.)

2. A ton of air travel intra-Europe is cheap. Use Google Flights to look for options. Personally, I'd rather be on a train with a dining/bar car and look at the scenery than deal with flying. Since you're staying on the west side of Italy, you shouldn't have major impediments to train travel. European train travel gets screwed up when you cross mountain ranges, and when you shift from Western Europe to Eastern Europe. Don't know why the latter is an issue 30 years after the wall fell, but what are you gonna do.

3. *IN* the cities, just use Uber and Lyft (Lyft seems to be less available overseas.) Subways/trains are easier when you don't know what you're doing than buses. The train method gives you time to figure out the timetable, etc. Bus, everyone, especially in Rome, will be angry at you three seconds after you start fumbling trying to pay. I like to just walk to get to intra city things. I've been forced by traveling companions to sit in Paris traffic and watch pedestrians outpace us on a 3 mile ride that cost 50 Euro and took 45 minutes. Coulda walked it faster.

Much of the glory of Europe (Paris, Rome, etc) lies in people and relaxation. You miss how many times Italians "take a coffee" during a workday if you're in a car of any sort. You miss the rando gelato stand that blows her mind. You miss *a lot* by not walking in major romance cities in Europe. I specify romance, because I don't doubt that if I ever set foot in Frankfurt, outside the airport, it's not so nice.