Train travel throughout Italy

https://www.trenitalia.com/en.html

They run the trains, they they should know.

Lisa, list the cities you’re visiting, and we can help. I have many of my train tickets for Italy for May purchased, so yours should be available on Trenitalia.com. You do need to know the Italian spelling, so let us know.

If you know when you want to take the train, you can save money purchasing ahead for the faster trains. For instance, I know that I like to take a train between 8-9:30am. Those cheaper tickets go quickly. You can see how much you will save by entering tomorrow’s date and an April date.

Between major cities like Rome to Florence, Rome to Venice, etc., there is another train company that also t]provides service on fast trains: Italo. Their website is a bit more user-friendly, and we like them for routes that they serve.

https://www.italotreno.it/en

With both Trenitalia and Italo, seat reservations are included in the ticket price for the fast (Freece trains on Trenitalia) and assigned, or you can choose seats yourself for an extra fee. On regional trains there are no reservations, and tickets must be validated before you board.

Do let us know what cities you are visiting and people will help you

At risk of repeating others, Trenitalia https://www.trenitalia.com/en.html and Italo https://www.italotreno.it/en are all you need. Avoid other third party sites.

Trenitalia will get you most everyplace (except a few private railways and metro transport), Italo can be a good comparison on the popular routes they run (Rome to Florence for example).

If you will have phone service, the Trenitalia app is handy and easy to use.

With some exceptions it's pretty darned easy getting around Italy on Trenitalia (I don't bother with private providers). An example of an exception would be the Chianti region, you'll have to rely on bus service and even then you'll be limited off exploring the region.

When you say several towns, sounds like the majority of your travel is likely on Regional trains for which you don't need reservations - you can just purchase and validate the ticket at the station on move days. Longer distances you would want to try and save some cash by booking in advance.

Enjoy your holiday.

Here is the Man in seat 61 beginner's guide to train travel in Italy. I think you will find it helpful with links to other good resources.
https://www.seat61.com/train-travel-in-italy.htm

You really don't need reservations as they lock you into specific dates and times. As your trip goes along, things change.
Buying ahead may get you a small discount, however. And trains between popular cities are very hour or two. Sometimes we like to sleep late--for example.

We often will wait until late in the day before we leave to purchase tickets. That way we don't have to deal with lines--if we use a ticket booth--and we figure out what the lay of the train station is. We often purchase tickets from vending machines with credit card.

Trenitalia will likely serve most, if not all of your train needs. There can be savings in buying the fast train seats in advance (Freccia trains), but those savings come with restrictions- the cheapest are nonrefundable and specific to that particular train. Regional trains can be bought at the station before you leave, or bought online ahead of time, but there won't be any cost saving. The Trenitalia app will be very handy if you have a data plan for your phone. In addition to buying tickets via the app, you can get up to date alerts, and info on platform numbers. But as mentioned, you must use the Italian place names eg: Roma, Firenze, Venezia.

Our destinations in Italy begin in Rome, followed by Assisi, Lucca, Modena, Bologne, Ravenna, Verona, Venice, Padua(Padova), and Milan. We'll spend 2 or 3 nights in each town and have our lodgings booked. Our plan is to get from one city to the next by train. Travel will be in April. Would appreciate any advice about the trains such as booking ahead vs. not, what system of trains to use, etc. Thanks ahead of time!

I believe you're adding unnecessary transportation time with Verona positioned the way it is on your itinerary. Verona is right on the train line running from Venice to Milan [corrected]. It requires a detour to go there between Ravenna and Padua/Venice.

Padua and Venice could be targeted either in that order or the reverse, because you'll be travelling through Padua on the way from Ravenna to Venice.

https://www.trenitalia.com/en.html serves all the places you're going with what look like the most direct available routings. https://www.italotreno.it/en would send you from Ravenna through Bologna on the way to Venice, which adds miles, time and probably cost. Some of your other travel legs would probably be fine on Italo, which might be less expensive.

Rome to Assisi is a direct regional train, costs 13.30 EUR.
Assisi to Lucca can be done all regional with a train change in Florence for 22.10 EUR.
Lucca to Modena is best done with a Freccia between Florence and Bologna.
Modena to Bologna is a direct regional train for 4.30 EUR
Bologna to Ravenna is a direct regional train for 8 EUR
Ravenna to Padova can be done all regional with a train change in Ferrara for 12.95 EUR, just 45 minutes slower than using a Freccia.
Padova to Venezia S. Lucia is a direct regional train for 4.80 EUR, just 14 minutes slower than a Freccia.
Venezia S. Lucia to Verona is a direct regional train for 10.20 EUR, just 16 minutes slower than a Freccia.
Verona to Milano Centrale is a direct regional train for 12.75 EUR, just 45 minutes slower than a Freccia.

So there you have it. Only one leg needs a Freccia train, and maybe a few more if you want to splurge and save a little time.

I have pretty much stayed with the trenitalia website-also download the app for your phone as it’s easy to purchase the Regionale tickets that way. I did a brief run through your destinations and as @Sam noted, the Regionales will serve you well for the majority of the segments. I would really look at a Freccia for Padova to Milano.

Off the subject a bit-are any of your accommodation bookings refundable? I only ask because if you don’t have many reasons to go to Modena, it is easy to enjoy it as a day trip from Bologna. Much easier to travel to Modena from Bologna than from Lucca which will require 2 train changes and quite a bit of time. I’d be tempted to up the stay in Bologna and do a day trip. Then again, if there are many sights there you want to see you might like a longer stay.

Back to the subject- you must use the Italian city name for from/to plus the proper station, ie; Venezia Santa Lucia, Milano Centrale, Verona Porta Nuova. There are others, but it can catch you up if you don’t know them. I often have to look on google maps to find the station name I want.

The only trains that require a reservation are the Freccia trains, although when you book the Regionales you will be asked to check in the day before or at the very least BEFORE you board the train. Therefore, the only train tickets to book ahead would be any of the Freccia that you want to use. Book ahead mostly because, the sooner you do so the more likely you can get a lower price. I’m partial to them as they are usually (not always) a direct train meaning I don’t have to change trains somewhere. I also like the faster times of travel so I have more time in the destination even if it means a better arrival for check in to my room.

Good luck and don’t let the trenitalia site make you too angry. Once you use it a bit, it gets easier.

Both Trenitalia and Italo have phone apps. Just like airline apps, you can plan trips, buy tickets, and use your phone for the boarding pass. If you have reservations the phone app will give you alerts. I used both train companies in Italy and never printed a ticket. For that matter Deutsche Bahn and in Dutch trains also have phone apps. I'm sure you'll find just about every train system in Europe has a phone app at this point.