Feb 26, 2016 - 9:38 AM
In winter the options are somewhat limited but you could travel from Milan to Tirano by train, then another train to Pontresina, another one to Zernez and a bus to Livigno. It takes about all day to do that, but the scenery is wonderful and it includes the southern half of the Bernina Express route. All details are in the timetable. Como is not en route, unless you would go all the way via Zurich, but then you'd miss the Bernina Express route.
If you have two days for this trip you could do Milan - Göschenen - Andermatt - Chur (Glacier Express, partly) - St. Moritz (Bernina Express, partly) - Zernez - Livigno.
I think you need to study the timetable for your travel date, check the map, and see which options fit your requirements.
I don't know the Italian pass you mentioned, sorry.
Last modified on Feb 26, 2016 - 9:40 AM by Arno