Train Bologna to Varenna 16 Oct Advance or at Bologna Central

1. yes.
   
2. yes, easy to purchase from a machine (or counter) at Bologna station (select English option on first screen; some machines are card only, some are cash or card, it will say on front of machine) or online anytime.
3. Look at the trenitalia website and decide if the savings are worth being locked in to a specific train. Full fare Bologna to Varenna for two people on the fastest trains is 110 Euro, that is the most you will pay if you wait until day of to buy. Some trains on that day are showing discount fares for 2 people as low as 62 Euro, (or as low as 44E for a slower train), but those fares are generally non-changable, you can decide whether the savings are worth being locked in to a specific train now.
4. Fast train tickets have a reserved seat on a specific train and don't need to be validated. Regional tickets (e.g. Milan to Varenna) usually need to be validated; if in doubt, just insert in validation machine. Have a great trip!

You can save quite a lot if you buy online now. Looking at the 10:56 Frecce departure from Bologna Centrale, with a single change at Milano Centrale ( total journey time 2.5 hours), I see the Base fare is 96€ (2 people). The “Me and You” fare for 2 is 48€, or half as much.

There is also a “summer special” for 37€, but you need a Carta Frecce for that.

This route gives you 22 minutes to change trains at MilanomCentrale, ,which should be plenty of time. But if you miss the regional train departure, I believe the ticket is good on the next regional train. It is the fast (Frecce) trains that are reserved and can’t be changed. ( But confirm that with someone else).

Nobody will fine you because you time-stamped a ticket that did not need to be validated. It's just a stamp with today's date and it takes one sec. Do not try to time-stamp your phone!

When in Bologna, be aware that Italo's last minute tickets to Milan are usually cheaper than Trenitalia's, but this way you may have to make a separate purchase for the second leg.

Just as Dario says. You can't get into trouble stamping when you don't need to (I know the phones are getting thinner!! - 10 points to Dario for quip of the week) but you can if you don't and need to.

Thanks for your quick and informative responses. I won’t prebook.

You've received some great replies so far, and I have a few thoughts to add....

1. That trip typically uses a Freccia high speed train from Bologna to Milano Centrale, and you will only have one change to get to Varenna. The trip from Milano Centrale to Varenna-Esino will be via Regionale (operated by Tre Nord as I recall). Travel from Milan to Varenna is 1H:04M, and I usually sit on the left side (when facing front) to get the best views. It's a good idea to be ready to disembark promptly when you arrive, as the train doesn't stop for long. You'll go through a tunnel just before arriving. Be sure you know how to release the door.
2. Yes, it's very easy to purchase tickets at Bologna Centrale. The automated ticket machines are very easy to use. You will likely get two tickets, one for each of the trains you'll use. You can also buy tickets online using the Trenitalia app on your phone.
3. The only advantage to pre-purchase of tickets is to save money on the high speed train. The Regionale is the same price whether purchased now or on the day of travel. I haven't checked to see whether Economy / Super Economy tickets are available for that day. One point to note is that the tickets for the fast trains come with compulsory seat reservations which are specific to train, date and departure time. If you miss the train you booked or board the wrong train by mistake, you'll be subject to hefty fines which are often collected on the spot.
4. Only the ticket for the Regionale needs to be validated, assuming it's purchased from a ticket machine and not online. You must validate only on the day of travel before boarding the train. Validated tickets have a "shelf life" so if you validate early and the the ticket expires, again the possibility of hefty fines. The ticket for the Freccia train will specify your coach (carrozza) and seat (posti) numbers and you must sit in the assigned spots.

Given the fact that you're going to be dropped off "about midday", I probably wouldn't buy tickets in advance. If you were late getting to the station and missed the train you booked, it would be a darn nuisance. If I were making that trip, I'd just buy tickets for the next departure at Bologna Centrale when I arrive there, using one of the automated ticket machines OR I would buy the tickets on the Trenitalia app on my smart phone. I always have full cellular service when travelling (not cheap but useful) so can buy tickets when needed.

1. If you buy the ticket to Varenna it means just that. You will go Bologna to Milan and then change to Trenord to Varenna. 2/3. As people have mentioned you will pay more for the fast train if you buy day of the trip. You can buy the "Base" ticket which is easy to change to an earlier or later train if your plans change but you'll need to stand in line speak to an agent to get that done. I would really recommend the Trenitalia app - you can buy tickets on it without waiting in line for the ticket machines or even from the platform as you jump on the train just before it leaves. You can also use it to track your trains and find out which platform your next train is on before you get off.
2. On the phone app there was a "Check in" for fast trains but not for regional trains. If you have a QR code for a specific trip on a regional train it shouldn't need to be validated. If you get the long old plane ticket looking ticket from an agent stamp it in the timeclock machine as you walk onto the platform. If you have multiple tickets treat each leg as it's own trip. eg Bologna to Milan is a ticket and then Milan to Varenna will be a ticket.

Have a great trip,
=Tod

Ken is 100% right, but let's repeat it once more for everybody's peace of mind:

No train ticket purchased online needs to be time-stamped

(aka validated if your children's dirty dream was to work for Trenitalia).

It doesn't matter if you are travelling on a Regional or an Intercity or some Freccia-something train. It doesn't matter if you print out the pdf with the QR / PNR code or not, either. Translate "Online purchase" as "I can freely board the train I bought a ticket for on the official site / app".

Thanks for all your inputs. My tour director, who will be dropping us at Bologna, says that it typically is about 11:30 am so the train leaving at 12.11 should be fine. He did note that traffic and road construction / accidents can impact timing. I’ve bought the tickets which will combine the 2 companies to get the least cost train / best timing to Varenna. I’ve also booked all my other trips: Varenna to Stresa, Stresa to kastelruth, Kastelruth to Rome. Tomorrow I will buy tickets @ Rome Termini to Orvieto leaving at about 10:20 to start my Italian train travelling. This seems like a lot of train travel but at least I don’t have to drive and we will have 3 nights in each place ie 2 full days.
Rome has been interesting. 4th time to Italy and 1st time to Rome. We are staying in Monti area and have walked to a number of the recommended sights in the area and will pick up some in more detail and accessing by public transit or taxis when we return to Rome at the end of October.
Thanks.

Hi - it sounds like you are all set. I wanted to add that we returned from Italy yesterday and took a train from Florence to Milan Central and transferred to the regional train to Varenna-Ensio just a few days ago and it was very easy. The Regional train was one track over from our arriving train from Florence. Just check the boards when you arrive and you should not have any problems. Have fun!