Traveling through Italy at the end of June and need some advice on purchasing train tickets

Also try http://www.trenitalia.com/tcom-en

RailEurope and ItaliaRail are travel agencies reselling tickets sometimes at a substantial mark up and do not show the full schedules. Use trenitalia - the national rail site. Also Italio is a private train company running on trenitalia tracks. I would start with trenitalia.

If available, you can purchase discount tickets on line from either company. The discounted tickets are limited, numbers vary by train schedule, and should be considered no change, no refund type of ticket. Miss the train and the ticket is dead. The except is the Regionale trains that are never discounted and those tickets should only be purchased at the train station.

Hi George -
The websites you should be using are Italy's national rail site....

http://www.trenitalia.com/tcom-en

...and Italotreno, which is a private rail company serving many Italian cities, including those you're going to be visiting.

http://www.italotreno.it/en

All of the trains you're going to want to take will be 'fast' types, with reserved seating in specific carriages. It's always possible to just purchase tickets the day of your journey BUT buying ahead can land you some nice price breaks when available. Getting the best price does mean committing to a specific train at a specific time, and purchasing 2nd class super-ecomomy or economy tickets. Super-ecomomy tickets allow no refunds or changes, and economy tickets can be changed for an additional price.

Editing to add: Italo's version of Trenitalia's super-ecomomy ticket is the "low-cost" ticket, and their 2nd class is the "smart" tier. You can always spend the extra $ for a higher comfort tier if you wish to but we've always traveled 2nd class and been perfectly comfortable.

It's usually not recommended to pre-purchase super-economy tickets for a train journey taking place the day of arrival, in case your flight is delayed.

Getting to and from the Rome airport (you're flying in/out of Fiumicino?) will involve an express train, taxi or express bus, depending on budget and what suits you best. We can cover that later.... :O)

The stations you're most likely to be using are:
Roma Termini
Firenze S.M. Novella
Milano Centrale

This could change depending on where your accommodations are but those are the biggies used most often. I will mention that some RS posters have found the Italo site a bit more user friendly than Trenitalia's but do compare $$ on both.

This should be enough to get you going but please give a shout if it's not?

Just for fun....
Without having your dates, I just plugged a journey from Roma Termini to Milano Centrale into Italo for a random June 14th day (5:00AM - 14:00PM) and am seeing prices of 23.70, 38,90 and 45,90 depending on desired departure time. As it's a considerable distance, these fares are pretty attractive, IMHO!

Buy your tickets in advance as mentioned above. One question though, why go back to Rome? It is much easier to fly into Rome and out of Milan, which saves you two travel days and the expense associated with them. After seeing/doing everything you want to in Rome take the train to Florence and do the same. Then take the train to Milan for the rest of your stay and fly home from there. That way you only have two short 2 1/2 hour train rides instead on one long and two short ones and they will be cheaper. If your response is that you've already bought your plane tickets go talk to your airline and see if they will make the above change to your itinerary. While they may charge you a change fee, it will most likely be less than you will spend on your present itinerary to go back to Rome, plus you gain the extra time for sightseeing instead of being on the train. Sometimes if you get the right agent they will waive your change fee, all depending of course on the airline, the category of your ticket and how far in advance you make the change. Unless you're spending most or all of your time in or near the city you fly into it is rarely a good idea to fly round trip. Good luck.

Trenitalia runs the trains, sets the prices and publishes the schedules. RailEurope is just a re-seller that doesn't run anything: they can't sell tickets at a lower price.
When you see big differences in prices and/or travel times, there must be a mistake somewhere:

1. You did not enter a departure hour on trenitalia, hence you're not seeing the same trains on the 2 sites.
2. Trenitalia.com always shows the price per group, re-sellers per person
3. You entered a date after the next timetable change. While Trenitalia shows only those trains that have been already uploaded on the system, RailEurope makes a bet on the next schedules to be similar to the actual ones. A bet with its customers' money!

If you don't like trenitalia's official site, you'd better use italiarail.com: it's an authorized dealer that has a direct access to the actual schedules and that can sell discounted tickets. It is also more user friendly for foreign customers, especially if you travel with children.
Italotreno's discounted fares have been cheaper than Trenitalia's since December 2016. Always check www.italotreno.it/en before purchasing train tickets: savings can be quite big and Italo's complimentary wi-fi works better!

Rail Europe is not "making a bet" on the timing of summer train schedules. Rather, they have opened summer train departures for sale in batches (3 so far), starting with the faster and international trains that Trenitalia and Italo have provided them. Nobody's selling tickets for Regional trains past the June schedule change, since those are the last to be confirmed. Darioalb may be recalling a procedure from a few years back, but that's not how it works now.

One question though, why go back to Rome? It is much easier to fly
into Rome and out of Milan, which saves you two travel days and the
expense associated with them.

To Jim's (very good) point, flying into one city and out of another would have saved you considerable time and some $$ besides. I'm just guessing you chose to fly in and out of Rome because you got a good price on your airfare? If your tickets can't be changed to fly you into Milan and out of Rome without incurring considerable expense, it's maybe just good information to file away for next time?

To Jim's (very good) point, flying into one city and out of another would have saved you considerable time and some $$ besides. I'm just guessing you chose to fly in and out of Rome because you got a good price on your airfare? If your tickets can't be changed to fly you into Milan and out of Rome without incurring considerable expense, it's maybe just good information to file away for next time?

We got a really good deal on the airfare (had to book it then for fear of losing the price) and didn't decide to go to Milan until after we had already booked. We are unable to change the flight without an additional $1,000 charge for the tickets.

It is definitely something that we'll have to consider next time, though.