MSPeconomist

IMO Italy has an higher risk of things going wrong than countries like Germany and Japan, and a smaller risk than parts of Latin America, although I haven't heard anything about upcoming major strikes scheduled or anticipated for this summer. [I don't think the OP has disclosed when the trip will occur.]

whimsey21

The trip is in July...

Perche

There is no particular risk of things going wrong in Italy. I had to be in Queens, New York City for the last month. The Long Island railroad was almost always late, and when you get to JFK it is truly like Joe Biden said, "a third world airport."

Most cities in Italy function better. I needed a taxi from Penn Station to 5th Avenue and 96th street. Penn Station is a pretty busy area, where you would think there would be lines of taxi, as in the major train station in Rome, Naples or any other Italian city. There were no taxis, I just started walking the 60 blocks, but eventually about half way there a taxi stopped just in front of me to let someone out, and I got in. I was 45 minutes late for the meeting. That's not going to happen to you in a major city in Italy, barring an unusual event.

You make a good point because I went back and forth with the OP several times before giving an answer because he didn't give enough details to work with. I was going to ask one more thing, "when are you going," but I figured that's enough back and forth, and just suggested one possible itinerary. As you indicate, the dates make a lot of difference. I've been in Bologna in August. I went there because I was renting an apartment in Modena during August. There were no open restaurants. I went to Parma, and there wasn't really any place to eat there. Every now and then you might stumble across a bad restaurant, but that's about it. I was so hungry that I moved to Bologna. It was the same thing. There was no place to eat. Everything was closed, except bars where you could get coffee, wine, and old pastry. Every now and then you would find a restaurant to be open. Except for places like Rome, Torino, Naples, or anyplace south of Naples, mid to late August is not a good time to be in Italy.

There are times and places for the different cities in Italy, depending on the calendar. In July I would not position myself in Pisa, or in Florence. Bologna will be better. Bologna is a college town, sort of like Boston. The oldest university in Europe is the University of Bologna, founded around 1080, and continuously holding classes since then. It's better when all of the students are there, at least when I pass through. In the summer it gets a lot more quiet, and I wouldn't go there in late August because it's dead. Pisa, I wouldn't suggest at all in July and August. Piazza dei Miracoli, I think that's the name of the plaza where the leaning tower is, is one giant bus stop for tourists queuing up to take a photo making believe they are holding up the Leaning Tower of Pisa. Then you go to the "old town" which is full of department stores and chains, like H&M, Zara, etc. Bologna is much better, and it's completely different from Florence and Pisa. An extra 10 minutes on the train makes it worth it.

Italy closes down from mid-August until the first of September. Pretty much the only places open are Rome, Florence, and Venice. I was going to ask the OP when he was going, but I already asked enough clarification questions. If he is going in the latter half of August, the itinerary I recommended would be off the table. If he is going another time, and he's travel wise, and can deal with trains and lack of sleep as he says he can, it is possible to do the itinerary I suggested.

The way I travel, like you, I wouldn't want to spend a night in Florence, a night in Arezzo, and a night in Bologna. But if someone says they are OK with sleeping on a train and want to see as many cities as possible, the itinerary I suggested, or any variation on it, is plausible. For sure, stay in the city of the departing airport on the last night.

Even though the Italian train system north of Naples is one of the best in the world, and hands down beats the BART in San Francisco, and the whatever you call it non-functional system in NY, it's a bad thing to have to keep looking at your watch on your way to the airport in Italy, worrying about the time, and how long the lines will be.

I would add this, Florence is really bad in July. It doesn't close down for the latter half of August like most places, but in the summer it is very hot, miserable, and over-crowded. Unlike Venice, where it is easy to escape the crowds by staying away from San Marco and Rialto because those are the only places people think exist in Venice, you really can't escape the crowds in Florence or Pisa unless you go to nondescript neighborhoods where there is no point going to. Bologna is not on the tourist map like Florence and Pisa, which makes it a better place to be during the summer. Except in August.