Is Monteross to Brig a viable alternative?

I think you’re right in that you might be overthinking!

Milan to Chur in 4 hours sounds like you would be taking the bus for part of the way? I’ve no idea how pretty (or not) that bus journey will be, but you’re missing the Glacier Express.

For sure, Chur-Tirano on the Bernina Express is the highlight here. 

It’s a little difficult to follow your exact plan. If you post a screenshot of the journeys & times you plan to take, like I did in your previous post, I can advise better.

What app are you using? I keep using Google and double checking bahn.de, but I am not yet looking at individual trains, just average travel times so I can make sure it’s workable. Bahn.de doesn’t seem to even have a Tirano to Varenna 

Yes Tirano - Varenna isn't yet on planners as Trenord/Trenitalia just released its timetables a few days before the yearly change. They should appear in a few days.

So what have you booked at the moment ? 1 night in Varenna 2 days after Monterosso or straight after ?

I'd say that Milan - Brig - Chur takes longer than 6h unless you are directed via Zurich (missing all the scenery) : probably what's happening here. We had posted a possible itinerary via Brig, let me add a screenshot here.

I don't think Monterosso - Brig - Chur is possible in a day and I wouldn't recommend it for sure ! You could do Monterosso - Brig - somewhere along the Glacier Express journey (Andermatt isn't that beautiful but it's conveniently located) in a day and continue the following day to Varenna.

DAY 1 :

- IC Monterosso - Milano Centrale 10:33 - 13:53 3€ reservation

- EC Milano Centrale - Brig 15:20 - 17:16 13€ reservation

- R Brig Bahnhofplatz (front of the station) - Andermatt 17:23 - 19:20 (unlikely) or 18:23 - 20:20

Unfortunately there are less trains running between Milan and Switzerland via the Simplon route this year (due to works) so as you miss the early morning trains coming from Monterosso you must wait for the afternoon ones (or take slow regional trains).

DAY 2 :

- R Andermatt - Disentis/Mustér 09:28 - 10:39

- RE Disentis/Mustér - Reichenau-Tamins 10:44 - 11:49

- IR Reichenau-Tamins - Samedan 12:08 - 13:45

- R Samedan - Pontresina 13:48 - 13:57

- R Pontresina - Tirano 14:08 - 16:23

- R Tirano - Varenna-Esino 17:08 - 18:34

Don't worry about the tight connections, they're all guaranteed (aka the train will wait). You can avoid a train by going all the way to St. Moritz (small detour) and make a little break there. Trains run hourly until Tirano.

Try searching for today - 9 Dec, and the trains show up. Unfortunately the timetable change on 10 December means times are still not published for these services after that, but you can assume the times will be similar.

They do appear to be visible on the train operator’s own website:  https://www.trenord.it/en/

Again, the timetable information for April is incomplete. If you search again for today, you should see the Intercity trains taking 3h.

You can assume they will be available in April, even if the exact time changes by a minute or two.

That Google Map option is sending you back over the Bernina Pass, where you’ve just come from(!), to take a bus through Switzerland and then two trains to Varenna. Probably because it doesn’t know about the direct Trenord trains.

As we said before, Google Maps is certainly a useful tool but it’s only one part of planning a journey. You need to sanity check anything it’s told you.

Thanks for such a detailed update. This is teaching me so much about life in Europe. You are obviously very comfortable with these timetables, whereas I get nervous. E.g., you’re suggesting getting into Andermatt at 20:20. Regardless of the time of the year, at that time of the night, it’s dark where I come from, and things are starting to wind down. Unless I knew the place well and I was staying at a 4 or 5 star hotel, I would probably not think of making my way to accommodation that late, they’d probably be closed. So much for me to experience.

To answer your earlier question, I have currently booked 1 night at Monterosso, 1 at Milan, that I am thinking of cancelling so I can have an extra night at another location, 1 night at Chur and 3 nights at Varenna. Your plan would see me cancelling my night in Milan, changing my night in Chur to a night in Andermatt and making Varenna late at night. 

I will study the plan and reconsider options when the full schedule is released in a few days. I’ll also have to check what check in times my accommodations will allow (I know the one in Vence wants an extra 30 Euro if I check in after 7), how far from the train station they are and what the transport from station to accommodation is like. 

Thanks very much for taking so much time to plan that all out for me. I appreciate your effort!

I find checking the area out on Google Streetview helpful if I’m unfamiliar. And Timeanddate can give you sunset times and typical weather for the time of year you’re going.

Switzerland does tend to shut down early - and often completely on a Sunday, which often catches people out! - but arriving in Andermatt at 2020 you should be able to find some life in the town. I wouldn’t hang around if you want to eat though. (Or perhaps pick up a picnic from the Co-op during your wait at Brig.)

I don’t know where you’re booking your accommodation, but if it’s a small B&B through Booking.com or similar, they often have an option to contact the owner. You can then check that they are happy with arriving at that time. They usually are if you contact them; what they don’t want is someone who gives no indication of what time they might arrive, and turns up unannounced at midnight!

For a short overnight like this, I tend to pick somewhere within a few minutes walk of the station.