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Planning for Sept 2025 - help with train and itinerary

Hello! There is so much helpful advice on this forum. This will be our first trip to Switzerland. We love hiking (easy/moderate) and charming towns. Flying into Milan to stay in Varenna on Lake Como (first time here too) so we can take the Bernina Express into Switzerland. I think I will need the 15 day swiss travel pass (flex).
I've put my itinerary below with questions. I'd love and appreciate any answers or suggestions!

Varenna on Lake Como (4 nights)

Varenna to Chur trains
QUESTION: is it doable to take train from Varenna to Tirano to catch Bernina Express to Chur in one day?
QUESTION: assume we should stay overnight in Chur since we are heading to Zermatt?
QUESTION: Would it be better to do Zermatt or Wengen first?

Chur to Zermatt (stay in Zermatt 2 nights)
QUESTION: Thinking we'd take a faster train (not Glacier Express) to Zermatt??

Zermatt to Wengen (stay in Wengen 4 nights)

Wengen to Lucerne (stay in Lucerne 3-4 nights)

Lucerne to Amsterdam
QUESTION: is this a doable train trip? or should we stay overnight along the way? if so, suggestion on where?

Thank you all! Kathy

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Varenna to Chur trains

QUESTION: is it doable to take train from Varenna to Tirano to catch Bernina Express to Chur in one day?
Yes, very doable. You could also just take regular trains and skipt the expensive seat reservation with exactly the same scenery.

QUESTION: assume we should stay overnight in Chur since we are heading to Zermatt?
There or Pontresina.

QUESTION: Thinking we'd take a faster train (not Glacier Express) to Zermatt??
That will be a train to Zurich, then a train to Visp, then a train to Zermatt. Not that scenic except part of the way to Zurich and Visp to Zermatt. It will get you there in 4 1/2 to 5 hours.

Lucerne to Amsterdam
QUESTION: is this a doable train trip? or should we stay overnight along the way? if so, suggestion on where?
There is a night train from Basel to Amsterdam if that interests you. Otherwise, stay along the Rhine in Boppard.

Don't bother with the Flex Pass. A 15-day 2nd class Swiss Travel Pass is only 20 CHF more than an 8-day Flex Pass, and you will find plenty of use for it, even on non travel days.