Multiple train trips from Milan

ar,

Those are all relatively short trips, so I'd suggest just buying tickets at Milano Centrale, either at the staffed ticket office (often a long queue) or using the ticket Kiosks. Here's some information on each of the segments you mentioned.....

• Milano Centrale to Brescia - that route is serviced by both Freccia and Regionale trains. As you want a "variable departure time", using Regionale trains would be best. There are no discounts when buying advance tickets on those so just buy a few days prior to the trips. The tickets don't become "usable" until they're validated, but you MUST validate prior to boarding the train on the day of travel, or risk hefty fines! DON'T try to save time by validating the day before travel or whatever, as they are only valid for about six hours once stamped, and will have expired by the time you actually use them.
• Brescia to Bergamo - these will most likely all be Regionale trains. Again, buy your tickets a few days before travel but be sure to validate them prior to use.
• Stopping on the way back from Brescia to Milan - this is possible, but you'll probably have to buy separate tickets for the return trip. An intermediate stop in Bergamo would be possible but you MUST use a Regionale train and you MUST be sure that the duration of your stay in Bergamo is within the validity period of the ticket. AFAIK that would allow you to disembark in Bergamo for a few hours and then continue to Milan using the same ticket.

Of course the simplest and most flexible solution would be to simply buy Regionale tickets for each segment and then just validate as you use them. The tickets are cheap so there won't be a huge cost for that. You can check all the soutions using the Trenitalia website.

It depends on the train you use.

If you travel on the higher speed Intercity or a FrecciaBianca trains, you must specify which train when you buy the ticket, because tickets are specific to the train. They work like airplanes. Like with airplanes you can't just walk into any plane, you must get on the specific airplane your ticket has the reservation for.

Regionale trains are commuter trains that work like a subway. You can get on any regional train on that segment. However you must remember to validate your ticket before climbing aboard. Simply insert it inside one of the validating machines along the platform. The machine will date/time stamp your ticket. You have then 6 hours to complete your trip.

The distances you are traveling are short. Therefore the regional trains aren't that much slower than the faster trains. For example from Milan to Brescia (your longest segment) is 46 min. on a fast train (FrecciaBianca) and 68 to 75 min on a slower Regionale.

There are no discounts on Regionale trains if you buy ahead. And I don't think you can buy ahead online anyhow (never done it myself). But you can buy them on the spot or a day or two earlier at the station or travel agency.

There are discounts if you buy ahead on a FrecciaBianca. However if you buy a discounted ticket, it's not refundable or non changeable if you change your mind or if you miss the specific train you book.

These are some sample prices on a one way 2nd class ticket for Milano Centrale-Brescia (your longest segment)
FrecciaBianca (46 min journey)
BASE (full fare)= €21.00
Economy fare= €19.00
SuperEconomy fare=€9.00

Regionale (68 min journey)
BASE= €7.30
(no discounted fares on Regionale)

There are some guidelines:
- fast train tickets are issued for a given train, are not valid on any other train and do not allow interruptions in travel
- regional train tickets are generic and can be used for any regional train; you must stamp the ticket before leaving; you can interrupt the travel midway, but you have only 6 hours to complete it from the moment you stamp the ticket (well, actually a bit more, as if you are traveling on a train when the 6 hours expire you are allowed to stay on the train to destination without stopping).

As the ticket office in Milan is often crowded, I would prefer to buy tickets a day or two in advance from a travel agency - the choice between open and closed tickets depends on type of train. Probably a fast train is not worth the extra expense on such short stretches.

Please note that the shortest possible itinerary from Brescia to Milan is via Treviglio, not via Bergamo, so an ordinary regional ticket Brescia-Milan does not allow a stop in Bergamo because you are not supposed to transit through Bergamo. I do not know if you would need separate tickets or a Brescia-Milan ticket via Bergamo (more expensive than the ordinary one as the itinerary is longer) is possible - this would be a thing to ask to the ticket agent.

Thank you all for the very useful information!