FCO Customs and Rail Pass questions

I am trying to figure out who his "leader" is and what is his authority to tell him he has to prepurchase a train ticket. If he ignores his "leader", will he be disciplined?

He can buy a full fare ticket that is changeable. If he is late, it will take time to change it. If he has the Trenitalia app on his phone, that would help.

I"m sure it's his study abroad instructor (or coordinator) who has given the group their instructions. I assume you mean he's supposed to pre-purchase for his day of arrival? All of the students will have received the same instructions. Just buy something changeable/flexible. When my son did a 3 week study abroad, there were a few edicts like that that seemed unneccessary, but sometimes when it involves a something like this; just go with it; and plan for all sorts of contingencies. College kids are flexible and resourceful with apps and social media to figure things out, that otherwise causes undue stress on us parents.

Railpass not really useful in Italy
He can just buy point to point tickets as he needs them

Have him get both the Trenitalia and ItaloTreno apps

Trenitalia is the state run train -regional and fast trains

ItaloTreno private company-fast trains only on selected routes

Use the Italian station names
Roma Termini
Firenze SM Novella
Venezia S Lucia
Etc

Helpful site
https://www.seat61.com/train-travel-in-italy.htm

What I used to do when on business trips in Italy now knowing in advance which train I would be taking is buy a "base" ticket for a relatively late train.

So buy a ticket Fiumicino - Florence for a train that leaves eg. 5 hours after touch down in Rome. Buy it using the Trenitalia App.
Then when you land get out your phone while you are waiting for your luggage, and move your reservation forward.

You can also buy Fiumicino - Florence with Italo, as they also sell regional tickets (and Leonardo Express tickets) in combination with their own trains. A flexible ticket on Italo is slightly cheaper than on Trenitalia.

There are normally always seats available at the last moment for most Rome - Florence trains, as there are lots of trains on that route.

I recall that we had prebooked train tickets from Rome (or maybe Florence) and arrived while the previous train was till at the platform - the ticket inspector told us to get on that one and sit anywhere.

Thank you everyone - yes it's his study abroad instructor who is requiring the advance purchase. I'm assuming they've had one too many kids land and say "I don't have a way to get to the next town" etc.

He has already downloaded the apps - thanks for the tips! He will purchase a "base rate" seat for later in the day and then just move it up on the app.

They are not arriving as a group which I find odd, but it's how they do it. This is all part of the adventure and learning experience - hopefully a few of the students will be there together and help each other.

I appreciate all of the insight! Thanks again!