Train Bookings: Point to Point or Pass? Looking for advice

Book the high-speed train tix online now, as they will rise in price the closer you get to the train’s departure date.
There are two train companies that service high-speed routes: state-owned Trenitalia and privately-owned Italotreno. You can see both companies trains at www.TheTrainline.com. The best prices will be at www.Trenitalia.com and www.Italotreno.com
The high-speed train tix you will want for your trip will be: Roma Termini to Napoli Centrale ( You then can take the local commuter train “The Circumvesuviana” from Napoli to Sorrento or the Campania Express);
Napoli to Venezia Santa Lucia; Venezia Santa Lucia to Firenze Santa Maria Novella; Firenze Santa Maria Novella to La Spezia ( local trains then travel from La Spezia to most Cinque Terre towns). There’s no need to buy local train tickets in Italy in advance as there’s no cost savings for doing so and local trains do not sell out. They may run out of seats- but you can always stand until a seat becomes available.

Thank you Kenko. Would booking online and using the emails be just as efficient as an app? Thanks.

Apps are better because they retain your info ( passport number, exact name as it appears on your passport, etc) from the first ticket purchased and you don’t need to re-enter all your info for subsequent ticket purchases— it’s already there. If you have any problem with Trenitalia’s platform— just buy their tix through The Trainline which may add a small 3-5% commission to the ticket price.

Thank you once again Kenko. If an app is better, it will have to be Italo as I cannot download Trenitalia in Canada and if I download it in Italy I will lose all my Canadian apps (yes that's frustrating).
Cheers!

Edited

I will suggest familiarizing yourself with European train services by reading through the Man in Seat 61 website. https://www.seat61.com/

Booking your Freccia trains in advance can save both time and money. Booking regional trains in advance may just save time. Dont just keep the tickets in your email attachments though. Save them in a document folder (or Tripit app if you use it) in case you find yourself without data or wifi. I also print them out at home as a backup, because I don't 100% trust relying on a single source. Those who have Apple or Google wallet often use that to store their tickets.

I'd still recommend downloading the app as soon as you get to Italy. You shouldn't lose all your Canadian apps because of that (if an app becomes unavailable, it would be because it is limited to certain geographic areas) Besides tickets, it will provide info on train time changes and station track locations, as well as the ability to buy additional tickets. By the way, will you be getting an esim to use in Italy, or are you relying on an international plan on your existing phone plan?

As for Eurail passes, they are rarely a saving. The Man in Seat 61 also discusses this.

Thank you CJean for the advice. I will definitely give the website a read.

Hi Mark. Definitely do not buy a pass. Other than that, don't overthink / over plan it. Don't worry if not easy to get the trenitalia app. You can create an account in the trenitalia website if desired, and it will store all of your journeys for easy reference. (trainline is also fine). Buy non-regional tix only when you know the exact time, they are good only for a specific train. For regional tix, just buy in Italy day of trip or day before, whenever convenient. Very easy to do in any train station in Italy, machines will have English option. Have a great trip!

You don’t need to use the Trenitalia app if you don’t want to or can’t. We do not, and we travel in Italy a lot. I book on the Trenitalia website from home (after registering as a user on the site) and put the ticket code on our phones as well as print out a copy. WE have saved a lot of money booking the fast trains well in advance. Or I book Italo, which we like a lot.

Whatever method you use to buy tickets, keep in mind that you must complete the transaction more than 5 minutes before the train's scheduled departure time. If you don't finish the purchasing process early enough, you will not have a ticket. I was told in 2023 by a very kind conductor on an Italian regional train that the fine for being in that situation is 50 euros. In the old days you could hop on a train, find the conductor, and buy a ticket from him/her at a slight upcharge; that is no longer possible (at least not on Trenitalia).

I have the Trenitalia app, but I've probably used the website more often. I'm not fond of conducting transactions on my phone because of the tiny keyboard; I'll often buy my ticket via my tablet while I'm in my hotel room, then I save the email attachment on my phone before heading to the station. I haven't yet tried saving tickets to my Google Wallet, but that sounds like a very good thing to do.

Note that regional trains do not offer seat reservations, and may involve SRO. I always need to mentally prepare myself for that challenge.
Have a great trip!

mark,

I also noticed that the Trenitalia app is not available in Canada. I've found Trainline to be a good alternative as it's possible to buy tickets for both Trenitalia and Italo (as well as numerous other rail networks in Europe). As I recall, they have a small service charge, but I don't find that to be a problem. Once you're registered on the site with payment information, the process is very straightforward. I've found their customer service to be very responsive, and I hope that hasn't changed.

I don’t understand why you think you will lose all your Canadian apps if you download something in Italy?
Can you explain?

There is an app called Trenìt that is available in Canada, it has both Italo and Trenitalia schedules on it.
I think you can buy tickets on it.
I don't know that for sure, as I don’t buy anything through any apps, just on my desktop computer.
I buy long distance high speed train tx in advance to save money, but just purchase Regionale ones as I go as there is no saving doing it in advance.
I use kiosks or ticket machines at the stations as I go.
In Italy all your train purchases bought online will show on both the actual train apps, and both also show you real time delays and departures.
When you buy tickets after signing up on each website (for free) with a user name and password; then your purchases will be visible on the apps.
It’s very easy to use both websites and both apps.

Thanks to everyone so far for their assistance! It's all been very helpful. There is a lot to get your head around when doing this and your suggestions have all been valuable.