Trains Italy
We traveled for 14 days in Italy last October, moving every three days, via train. We visited Milan, the Lake Como area, Portofino, Cinque Terre, and Venice. No timeshares.
We traveled with only carry-on luggage and could not have handled more. The Milan station had elevators/escalators but small town stations are not necessarily so equipped. Often we had to walk out from the station and carry our luggage down stairs, under tracks through tunnels and then up stairs to our track. The step up into to the train itself was often high off the ground. I am 5'4" and had some difficulty boarding a few of the trains, especially trying to handle my own luggage. That said, in Milan there were some boys hanging around the trains and one grabbed our luggage and handled it for us even though we protested. Then when my husband tipped him, he argued loudly with him that it was not enough. They do not officially work for the railroad and there are others like them that hang around the ticket machines to help people for tips. Be aware. Sometimes it is worth paying them if you are uncertain of how to use the machines or need the help. Other times they can be a nuisance. But I'm glad to see them trying to earn a living! They could be out doing worse!
We also found some of the trains packed, as we didn't pay the extra ticket price for reserved seating and usually didn't have a problem. One train though was filled with young teens. I boarded with an elderly lady who was using a cane and not one of the young people got up to give her, or me, a seat. We stood for half an hour until they got off before we could be seated. There must have been at least 30 of them in our car. Even in off-season, the trains to Cinque Terre, and moving from village to village, were standing room only. January should be a different story as I doubt you will find much open in that area. At the end of October they were pretty much closing the area down.
The majority of our trains were right on time and also wasted no time taking off again. We had one exception and that was when traveling to Venice and we missed our connection in Milan due to our first local train being late (it had to keep pulling over to let the fast/express trains pass) and had to re-book our ticket and rush to catch the new connection. It was a bit nerve wracking as the lines were long but we managed to make it.
I was quite proud of us for managing this type of travel for the first time, and at our age, 67. We usually rent cars when we travel but parking was going to be a problem in the areas we were visiting. I would travel by train again but pack even lighter!
We made up for any hardship experienced earlier by taking the Belmond Simplon Orient Express overnight from Venice to London to spend six nights in England before returning home. That was the experience of a lifetime in itself!