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@giofox
http://www.trenitalia.com/tcom/Offerte-e-servizi/In-treno-con-la-bici
According to the main railway company (national company) it depends which train you want to take. If you are doing Milan to Como, you'll probably end up taking a "Regionale" regional train, on which you can buy a bike reservation, and have the bike stored away in a specific car, fully assembled. I'd recommend staying within eyesight and/or locking it, as the car is accessible to other people.
If you want to take it as a box there are some limitations on size, see website above, but as long as you place it in a way that it doesn't obstruct people, I doubt anyone will come measure it, it's Italy after all..
Best option imho, ride from Milan to Como, May is a beautiful month to do that.