Buying train tickets now or in Italy?

The price goes up as capacity shrinks on major route high speed trains so it is better to purchase now. The regional trains you don't need to purchase in advance.

Depends on the cities.
Except for your arrival day, any high speed trains can be bought cheap now if you can live with a specific departure time for a nonrefundable ticket.
Example: Florence to Venice on Trenitalia can be bought now for a 9:20 departure on July 29 for 29.90 EUR vs 57 EUR day of travel.
Using Italotreno, same day at 9:39 departure in Prima (1st class) for 21.90 EUR vs 59.90 EUR day of travel.
Regional train ticket prices never change.

Thanks for the information. We are making the following trips:
Venice to Ravenna
Ravenna to Florence
Florence to Rome
Rome to Sorrento
Sorrento to Rome
Are any of these 'regional routes'?

Venice to Ravenna
Ravenna to Florence

These routes are covered by both two regional trains or a high speed (requiring a seat reservation) and a regional depending on the time you want to leave.

Florence to Rome
Buy this one well in advance. Either Trenitalia https://www.trenitalia.com/en.html or Italotren https://www.italotreno.it/en

Rome to Sorrento

The Rome to Naples portion of this trip you can save money buying in advance on the Trenitalia or Italotren sites.

The Naples to Sorrento portion is operated by two different train companies not associated with either Trenitalia or Italotren; these are either :

the Circumvesuviana (you can only buy this the day of https://www.sorrentoinsider.com/en/naples-to-sorrento-train-schedule)

or the Campania Express (you can either buy in advance or when you get there: https://ots.eavsrl.it/web/public/ots/ticket/index)

Sorrento to Rome
Same as Rome to Sorrento but in reverse.

Venice to Ravenna: Can be done with regional trains for 14.80 EUR pp
Ravenna to Florence: Can be done either way.
Florence to Rome: High speed train
Rome to Sorrento: Rome to Naples with high speed train
Sorrento to Rome: Naples to Rome with high speed train

If you know when you want to travel, I think it is worth considering buying tickets ahead of time even if there is no cost savings. I did this a couple nights before we left for Italy and I thought it made life easier even though there was no cost savings.

IF your flights are booked and your itinerary is set in stone - you're good to forge ahead with train ticket purchases. Again, if your plans are set and while there are no savings to be had on Regional trains, there could be marked savings when purchasing the long-distance high speed tickets.

You can also use both the Italotren and Trenitalia ap on your phone or tablet to buy and store tickets using the hotel wifi if you don't want to stick to where you are going on a given day in advance.

Use the official train sites to purchase your tickets
Both have easy to use apps as well

Trenitalia- fast trains and regional
https://www.trenitalia.com/en.html

Italotreno- fast trains. Sign up for their newsletter to get discount codes
https://www.italotreno.it/en

Info on train travel in Italy
https://www.seat61.com/Italy.htm

You’ll save a change of lodging if you go from Florence > Naples > Sorrento. Train 3 hours to Napoli.

Thanks so much for the information!

My method is to buy train tickets in advance if it is cost-beneficial and it is a train that I know I will catch. If the route is serviced by a regional train, there's no advantage to buying in advance. Think, Milan to Como. If I know I'm going to get up on, say, Tuesday and transit to a defined location, then I will buy in advance. Think Florence to Rome. Then, it's a lot cheaper to buy in advance and we can just jump on the train. If we have something scheduled before we get on a train, it's easier to buy when I get to the station. More expensive, yes but not having the stress of getting to the station for a specific train is priceless. Flexible tickets were on a par with same-day tickets. This works for us.

I just glanced over the previous replies, so don't know if this was already mentioned. If you buy tickets for the express trains such as the high speed Freccia, these are specific to train, date and departure time and can only be used on the one train listed on the ticket. If you board the wrong train, even by mistake, you'll be subject to hefty fines which will be collected on the spot.

The same fines apply if using locally purchased tickets for Regionale trains, and failing to validate them on the day of travel.

I used italiarail and had no issues and they were a lot cheaper for me. Worth looking into

Be aware that Italiarail is a US travel agent and they do charge commission on Italian train tickets. If you can, buy direct from the train operators, Trenitalia and Italotreno.

As with anything, you should always be careful. But there is a reason italiarail is a legit way to book tickets when in Italy. I saved $47 dollars using italiarail when booking our tickets from Venice to Florence. No need for a ticket, just show them the code on the email. I saved $24 when using Italiarail when booking our tickets from Florence to Rome. There are plenty of blogs from Italians that help explain and the general consensus is that there is nothing wrong with it, no need to scare people off. In the US, I have never bought a sports ticket straight from the team's site. I use stubhub, ticketmaster, etc. This is the same type of thing.

I just compared Venice > Florence, on both Tenitalia and Italiarail, August 12th @ 10:26am, for fun of course and Trenitalia was the lowest price in every category.

Both Trenitalia and Italotreno have apps where you can show your tickets on your phone, so nothing new there. You saved $47 and you were happy, you could have saved $52 by going direct. The only reason to use a 3rd party is if you are having credit card issues going direct, which can and does happen.

It should be obvious that ItaliaRail can't sell a point-to-point Trenitalia ticket for a single passenger at a lower price than Trenitalia itself. Period.

On the other hand, it's true that in two cases you can save money With ItaliaRail.

1. There are more passengers travelling together and buying tickets all at once. ItaliaRail combines different discounted fares (with different T&C!) into a single purchase. For instance, there are 3 passengers and only 2 SuperEconomy tickets left in one car: ItaliaRail will sell them 2 SuperEconomy tickets and one Economy Ticket. This way the final price for the all group would be lower than what they would pay with Trenitalia. Trenitalia.com is programmed not to do mix different fares because having a group of passengers with different T&C is a recipe for disaster on the ground. ItaliaRail is a webpage, not a train company: They couldn't care less about what happens in the real world.
2. They have another way to sell cheaper tickets, if you are going from A to C with a train transfer in B. ItaliaRail could sell you an Italotreno's ticket from A to B and a Trenitalia ticket from B to C, picking the cheapest tickets sold by the 2 competing companies on that route. Without mentioning that this way your connection would not be protected.

Again, ItaliaRail couldn't care less about what could happen during the actual journey. Their job is re-selling train tickets, not carrying people to their final destinations.

It is not a scam, just two different business purposes. Brandon could have actually saved some money, did he know the risks they were taking?

I think it ultimately boils down to your preferences. Are you a person who likes to have everything planned ahead and stick to a schedule? Buy in advance. Are you a person who likes to be spontaneous and change plans at a moments notice? Buy when you get there.

For my recent trip, I prebooked only the train from Rome to Lecce on my day of arrival. Every other ticket I bought day of. Some I even bought sitting at the train station about 15 minutes before the train arrived. I realize this would drive some people insane, but I loved the flexibility of it. I never had a problem with any train being fully booked.