A couple of basic train questions

If you buy Milan to Bologna online you can print out the ticket. It will come as a PDF similar to how you can buy airline tickets and checkin online and print at home

You can wait until you get there to buy Bologna to Ravenna as regional trains do not require seat reservations. Also you have the option buying the ticket with a live person who may be able to tell you what track.

You can buy both legs together or buy them separate- your choice.
I have bought separate legs when I want to pick my connection. ( Changes at Bologna are a good time to consider this)

Either way- your regional ticket is good for any similar train in next 4 hours

You'll want to take the fast trains between big cities and these come with assigned seats on a specific train. The earlier you buy the cheaper the tickets but you're trading economy for flexibility. If you're not taking a fast train the same day you're flying you should be able to decide when you want to fly and pre-buy your tickets if you want to. Tickets for fast trains are generally available two months ahead.

The state train company is Trenitalia - they run fast trains and local ones. https://www.trenitalia.com/en.html
.Italo is a private company that only runs fast trains. The service between the two is pretty similar. https://www.italotreno.it/en

Local trains called regionale tickets are always the same price - just buy them when you need them. Also if you have a reserved train and you miss it because of the train being late and it's the train companies fault they are required to re-book your ticket even if it is a restricted change ticket. Of course if you just miss a train with a restricted ticket the restrictions apply.

Download the Trenitalia app to check schedules, buy tickets, validate them for travel and track trains in real time.
Always validate your regionale tickets - paper ones at the stamp machine and electronic ones in the app. You should be able to import your Trenitalia tickets into your app so you should have them there in addition to printed versions.

Really good general train information here: https://www.seat61.com/train-travel-in-italy.htm

Have a great trip!
=Tod

The Bologna Centrale station is huge and complicated. See the guide here:

https://www.seat61.com/stations/bologna-centrale.htm

You will come in on the Frecciarossa train from Milan to the deep platforms (16-19) and then make you way up escalators and through corridors to the street level for the platforms for your regional train to Ravenna. follow the yellow signs for Bihari 1-11. The main hall with the ticket machines is adjacent to the platforms, so if you want to wait and purchase your Ravenna tickets there it is not too hard to find. These paper tickets from the machine (or from an agent at the window) MUST be validated with a stamp from the machine, so you will have to find one. There is a photo of the validation stamp machine on this helpful blog:

https://thetravelfolk.com/bologna-train-station/

You could also buy your regional tickets to Ravenna before boarding your train in Milan; just make sure to select the correct departure station (Bologna Centrale). Then you stamp it when changing trains at Bologna.

Or you can buy the journey as one ticket and print out both the Frecciarossa ticket and the Regionale ticket at home. Neither of these “print at home” tickets needs to be validated, nor can they fit in the machine.

Note that there is also an option for a “digital Regionale” ticket which you buy online and put on your phone. You say you do not want this type of ticket. But for the benefit of others reading here, and to avoid confusion, I will point out that the digital Regionale tickets must be validated in the Trenitalia app, after midnight on the day of travel but before you board the train. These digital tickets have a “checkin” link they send to your email (or you can access it in the app).

Most of the Trenitalia journeys offered online have 15-23 minutes between trains at Bologna Centrale, but I see that on May 22 the 9:10 departure from Milano Centrale has a 41-minute space between arrival of the Frecciarossa and departure of the Regionale to Ravenna.

If you want more time than that, you can book the entire journey on Italo. You will get a ticket on the Italo fast train from Milan to Bologna (also arriving at the deepest platform) and a regular ticket on the Trenitalia Regionale train to Ravenna. Italo bookings have a longer transfer time at Bologna, just over an hour, so the overall journey time is longer as well. But if you want extra time at Bologna Centrale, maybe to buy lunch, this is one way to get that.

We took the regional train from Bologna to Ravenna when we were there last March (a year ago) and it departed from the street level area (Platforms 1-11). I believe it was track 6, but can’t be sure about that. It will be easy to check the departure boards—-look for the regional train by scheduled departure time and train number. The end destination may be past Ravenna—-usually Rimini. But when you reach the platform the board there will display the train number, end station, and all the intermediate stops so you can confirm.

Thanks so much to everyone for the VERY helpful answers and explanations. Very glad to hear that one can still take a train without too much tech, lol. We haven't been to Italy since before the pandemic and I am feeling rusty!