Buying train tickets

How far in advance do i need to reserve?

There may be some discounts available up until the day before, but the earlier you buy, the better chance of finding deep discount nonrefundable tickets. There are also 2-for-1 Saturday specials on Freccia trains, and other deals for advance purchases. Regionale trains never need, or take reservations, and the price is always the same, even you buy a few minutes before departing with the mobile app. I haven't used it, so wait for others who have used it to chime in.

I haven't used the mobile app but I have used ticket machines in Italian train stations with no problem (some take cash, too), so that can be Plan B and buying from a staffed ticket window is Plan C - plenty of plan options!

Unless you're traveling around a holiday (when popular trains might sell out), the issue is likely to be cost. As in Spain, the price you pay for a ticket on an Italian express train (Freccia or Intercity) tends to increase as the travel date approaches. It is a matter of weighing cost vs. flexibility.

Like you, I prefer to keep my options open. That generally works well for me, because I'm a slow traveler who typically moves from one fairly small city to another. That puts me on regional trains, for which I don't have to worry about escalating prices.

I recommend that you make a list of the trips you expect to take. Then go to the Trenitalia website. Price each of your hypothetical trips for immediate departure (within the next 24 to 48 hours), recording the highest price you see for any departure. Then change the date to June 7-9, which is far out as fares are currently available. Record the lowest fare you see--the price you'll pay if you buy your tickets when they initially go on sale. The different between the lowest price and the highest price is the (maximum) cost of remaining flexible.

Perhaps you'll deem the fare differences not worth worrying about. If you have just one or two that make you say "Ouch", maybe you can figure out a way to pin down the timing for just those one or two trips and take advantage of the bargain prices when their tickets initially go on sale.

When the time comes to buy your tickets, you may prefer to use the trainline.eu website, because it offers both Trenitalia and Italo tickets. For any given trip, either one might be a bit cheaper.

When you're traveling to or from a smaller city, always pay attention to the total travel time before selecting a train. The more miles of Freccia/Intercity train on your ticket, the higher the cost will be. If you have to switch to or from a regional train as part of your trip, you may be stuck with quite a long layover at the transfer point. I've seen cases when the trip with a Ferccia component was just a few minutes faster than the trip that was all on regional trains, but the Freccia itinerary was much more expensive.

There are also times when it's worth considering a bus to avoid the high cost of last-minute train fare.

Edited to add: I missed at least one train in Italy while stuck in a slow-moving line at a ticket counter. If for some reason you cannot use the vending machines, allow plenty of time to buy your ticket.

I used the mobile app and it worked fine this past September/October. I don't recall if the app is in English but I used the Italian version without any issues.
It was very convenient and I didn't have to waste time going to the train station.
I did, however, booked my train ticket for the freccia trains (high speed trains) in advance in order to save money.

Most of the trains I took on my most recent trip were on Regionale trains, so buying a day or two prior to travel did not make a difference in terms of price.

Enjoy your trip!

I too used the Trenit app in Italy last year - very handy for buying train tickets on the fly, plus the app has platform information and real-time delay info (helpful if you are making a connection - that is you use the app while on the train before you get to the next station). it's nice to know what platform your connecting train will be on before you even get off the one you are on, especially for a tight connection.

I paid with Paypal in the app. Paypal tip: it defaults to DCC (Dynamic Currency Conversion) for foreign transactions, no matter what credit card you use if paying by card, meaning you'll get charged an extra fee potentially. But you can change the default in your Paypal account to get rid of that. I forget how I did it, but you can go in and change it. If you use a credit card with no foreign transaction fees with Paypal, you'll want to make this change to avoid extra, unnecessary fees.

Also, the Trenit app can be used to purchase tickets only up until 15 (?) minutes before the train departs, so don't wait too long to make your purchase. The ticket machines, by contrast, let you buy a ticket up until the train is pulling away so you can cut it a lot closer with the machines. I also have a chip and PIN credit card that I used to buy tickets at some of the machines, when I was winging it last minute with some trains. I used Trenit to book tickets when I knew in advance which trains I wanted. Regional trains don't cost more last minute so you can book those near pretty close to departure, but the faster trains with reserved seats tend to be more expensive (cheap seats sell out) the closer you get to departure.

So now I have the next question...How the heck do i get the app? I hate Apple's ecosystem. The app isnt available in teh US App Store, I go to the UK Store, and get the error that my acct isnt valid for the UK Store. Grrrr

itc,

As someone else suggested, use the www.trainline.eu website to buy tickets. They sell tickets for both major rail networks in Italy as well as some of the smaller ones, at the same price as the rail networks. You'll need to register on the site first, including payment details, but after that it's very user friendly. They also have a smartphone App and you shouldn't have any trouble downloading it from the "Apple ecosystem".

Once your payment information is accepted by Trainline, you won't have to worry about "chip & pin" credit cards. The reason you weren't able to download the Trenitalia app to your website is that it's likely not available on iTunes in some countries. I've also been unsuccessful in getting that, but it has nothing to do with Apple.

For future reference, Trainline also sells tickets for trains in Germany, France, Spain and other countries, so it provides "one stop shopping", depending on the specifics of the trip.

Thanks All!
Looks like the Trainline EU really is the way to go!