Switzerland by rail help please

A five day trip with eight stops? Have you looked t the actual train times between these locations and added up the hours of being on the train and waiting in train stations? That sounds like an ordeal to me, where you don't get much time on the ground anywhere. What exactly is your goal? Scenic train rides, or mountain experiences?

Thank you for your quick reply. We are mostly after the scenic rides, and not a lot of stops. The only reason I mentioned some of those locations as I was staring at a map of Switzerland and creating a potential route. This is our first time doing a scenic trip. Please feel free to make suggestions, they are most appreciated!

Ya, no way. 5 days? Pick 2 spots.
Maybe Tirano > St. Moritz > Chur > Zurich
OR
Tirano > Milan > Visp > Zermatt > Lucerne > Zurich

Are you coming from the United States and do you know that you will be able to sleep on the plane over
Jet lag factors into quality of the first couple of days.
The trains are like rocking cribs that will make one sleep deprived struggle to stay awake. It takes an hour to get from the airport to Milan Central Station where you then need to get a train to Tirano which takes another 2 hours. Then Tirano to Chur takes 4 hours. If I were you I would just stay in Chur or Pontersina and take your daytrips and Zurich the night before the flight back. Only go to Zermatt if the weather forecast the night before says it is going to be sunny. Otherwise you won't be able to see the main reason people go there : the Matterhorn.

On your first of those two options, since we will be flying into Milano, and starting there, any recommendations on where we should lodge, two nights here, two nights there, etc.? I really appreciate your input! I’m guessing we will want to go with the Swiss travel pass, and on these trains, we might not need any reservations?

Get the Swiss Travel Pass 4 day. You don't need train reservation or tickets with that. Just use the regional trains that the locals use on the same tracks that the Bernina Express tourist train run on from Tirano to Chur.

Stay 4 nights Pontresina it is between Tirano and Chur.
1 night in Zurich the day before the flight.
Someone will chime in here on hotels.

Regarding the comment about traveling from the United States, we will have already arrived in Italy, and had a couple of days to catch up before venturing up in Switzerland. Thank you for your comments and interest, feel free to make any other suggestions you might have, they are greatly

Really grateful for all of the suggestions, my wife and I are both retired, but active, and like to try and minimize our mistakes as much as possible. If you had any hotels, you would recommend in those two cities, we lean toward the more budget oriented. Much appreciated!

In 5 full days on the ground I would do the following:

Day 0 - arrival: head to Varenna by train from Milan.
Day 1 : stay in Varenna, see lake Como
Day 2 : head to Pontresina (or Samedan) via the Bernina Railway which starts in Tirano
Day 3 : stay in Pontresina (or Samedan), explore the area
Day 4 : stay in Pontresina (or Samedan)
Day 5 : travel to Zürich via the Albula railway through Chur. Spend the afternoon in Zürich
Day 6 - departure

If you have one fewer day, cut 1 night in either Pontresina or Varenna.

Hoping to get anyone’s input on this itinerary;
my wife and I will be coming up from Italy and flying into Malon in about a month. This would be pretty much a real trip, Starting in Tirano, to St. Moritz, to Zermat, to Interlaken, and ending in Zürich, where we fly out from. We have basically five days allocated for this. Is this realistic?

Editing Balso's comment, since this is primarily a scenic railway trip.

Day 0 - arrival: head to Varenna by train from Milan Malpensa airport..
Day 1 : head to Pontresina via the Bernina Railway which starts in Tirano
Day 2 : head to Zermatt on the Glacier Express after short connecting train from Pontresina.
Day 3 : stay in Zermatt
Day 4 : head to Interlaken via Brig, then to Spiez via the "Loetschberger" regional train, then to Interlaken.
Day 5 : head to Luzern on the Luzern-Interlaken Express train.
Day 6 - train to Zurich airport taking 70 minutes direct.

There you go. 4 scenic train rides in 5 days.

Sam's itinerary is optimal to maximize scenic train rides (perfect, even!) ... But you need to think hard about this: do you want to spend your vacation on trains (3 to 8 hours per day)? Scenic as the railways are, after a few hours I find such rides a bit boring. Your opinion may vary, of course!