Lake Como to Switzerland to Austria

Sounds wonderful. A suggestion, rather than staying in St.Moritz, book a hotel in nearby and much more charming Pontresina.

You have 9 stops on your tour and 24 days. If you want to go from St Moritz to Zermatt, might as well get it over with in one shot on the Glaciers Express. It is 8 hours, but pretty comfortable. You do get 10 minutes to stretch your legs on the platform at Disentis/Muster and Andermatt. Cut Bern, its out of the way from Berner Oberland and Luzern. And cut Vienna, it is too far out of the way unless you want to get a flight from there back to Milan. In St Moritz area, look at the Swiss National Park by Zernez if you want a bit more back country experience. http://www.nationalpark.ch/en/

Thanks for the suggestion on pontresina. I wondered about that. Any other suggestions on places to stay? Here is a rough itinerary.
Como, Switzerland, Austria itinerary
9/9 Flight
9/10 Arrive Milan evening
Sleep Milan
9/10 Lake Como
Sleep Como
9/11 Lake Como
Sleep Como
9/12 Lake Como
Sleep Como
9/13 Bernina express to St Moritz possible pontresina?
Sleep Moritz
9/14 St Moritz
Sleep Moritz
9/15 St Moritz
Sleep Moritz
9/16 glacier express 9 hours
Sleep Zermatt
9/17 Matterhorn/ glacier tour
Sleep Zermatt
9/18 Wengen
Sleep Wengen
9/19 Lauterbrunnen Valley
Sleep Wengen
9/20 Jungfraujoch
Sleep Wengen
9/21 Bern
Sleep Bern
9/22 Bern
Sleep Bern
9/23 Lucerne
Sleep Lucerne
9/24 Innsbruck
Sleep Innsbruck
9/25 Innsbruck
Sleep Innsbruck
9/26 Salzburg
Sleep Salzburg
9/27 Salzburg
Sleep Salzburg
9/28 Vienna
Sleep Vienna
9/29 Vienna
Sleep Vienna
9/30 Vienna
Sleep Vienna
10/1 flight Milan
Sleep Milan
10/2 last supper cathedral
10/3 flight home.

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You are double counting 9/10 as 1 night in Milan and 1 night at Como. So you actually have 23 nights.
I note that you are staying with Bern and short changing Luzern. Unless there is some special reason, I'd skip Bern, and go from Berner Oberland on the Interlaken-Luzern Express that goes over the Brunig Pass. So keeping 3 nights on Lake Como, everything moves up 1 day. 2 nights in Luzern and you are back on track.

So yes, looks good.

Thanks. Great suggestion! Any hotel suggestions? Boutique 4 star our preference 😊

Zermatt: Hotel Ambiance, last owner operated hotel in Zermatt.
Wengen: Hotel Silberhorn, not boutique, but a 4-star across the street from the train station.
Milan: Hotel Berna, short walk from Centrale station with good service, breakfast.

Remove Innsbruck and add the time to Salzburg and Vienna. After what you’re seeing in Switzerland, Innsbruck will be a let down.

Great advice. I will research further whether to drop Bern and Innsbruck from our itinerary. Any suggestions on Swiss travel pass?

For Lake Como, I suggest staying in Varenna, which is an hour from Milan on the train line running up to Tirano, where you will Class your Bernina Pass train. Note that you do not need to ride the Bernina Express scenic train; regular regional trains ride the same tracks hourly.

We love Alberto Milano in Varenna, staying in the top floor room in the annex known as Casa Rossa. But there are other lakefront hotels in Varenna, such as Hotel du Lac, that get great reviews as well.

You have 356 CHF pp worth of full fare tickets from Tirano to Zurich Hbf. A 15-day Swiss Travel Pass is 485 CHF pp. The whole question is: How many extra trips are you planning on when you are in Switzerland? Mountain lifts generally only get a 50% discount with a STP, but in the Berner Oberland, above Wengen, it only gives a 25% discount. However it does fully cover the Schilthornbahn to the top at Piz Gloria. It also covers the Mount Rigi in Luzern.

Overall, the 30-day Half Fare Card will probably save the most money. It costs 120 CHF, then everything is 50% off, including mountain lifts, trains, buses, city trams, lake boats. But you still have to buy tickets for each trip.

So if you stick to freebies like the Schilthornbahn and Rigibahn, and like the convenience of not having to stop and buy tickets for regular trains, then the STP wins. For saving money and doing anything you want, the HFC. Non of these covers reservation fees for the Bernina and Glacier Express trains.

Austrian train tickets can be bought now for cheap, but they are nonrefundable and nonchangeable, like airline tickets. Cost is 19 EUR pp for Zurich to Innsbruck, Innsbruck to Salzburg, and Salzburg to Vienna. Buy them at www.oebb.at/en.

Italian tickets you need are Regionale, always the same price and no reservations. so buy when you get there.

I agree with dropping Bern and Innsbruck, and I'd suggest adding some of those days to the Berner Oberland. Since you like day hikes, I've private mailed you our dozen favorite hikes in the region.
Along those lines, I wouldn't suggest Wengen as the best place to stay for that. There are simply no (great) trails originating from Wengen. True, it's a lovely town, but for hiking, I'd recommend staying in Murren, Lauterbrunnen, or Grindelwald, in that order.

As for Salzburg, you might check out via Google image "Eisriesenwelt" which is an ice cave above Werfen. You can take the train there, or sign up for an excursion there via Panorama Tours.

I thought about that as well but concerned Thant the weather may not cooperate. Thoughts?

Cindy,
For weather, I assume you are talking about the Swiss mountain towns?

True, but that's why I'd always recommend at least 2 nights in Zermatt, and 5 days in the Berner Oberland.
For the latter, there are things to do even in misty overcast weather such as Lauterbrunnen museum, walk behind Staubbach Falls (wet there anyway), Trummelbach Falls, boat trip on Brienzersee (especially if you have Berner Oberland Pass), which you should look into.

I just did much of what you want this past week only in the other direction. Here is what I wound up doing but in reverse.....

MIlan to Varenna (this is on the train route from Milan to Tirano where you pick up the Bernina Express..) Varenna is on Lake Como and you can pick up the ferry to almost any point. (I stayed at the Royal Victoria. Splurge for a lake front room.)

Train from Varenna to Tirano to pick up the Bernina Express. Take it all the way to Chur. Forget St. Moritz as not all Bernina Express trains go there. Stay in Chur. I stayed at the Post Hotel about a five minute walk to the train station. Nothing to write home about but clean. Definitely not four star. More budget oriented but I was only there one night. No, you don't have to take the Bernina Express but it does make photo stops at some points and slows down at others. I doubt the regular trains do that.

Take the Glacier Express from Chur to Zermatt. This train is slightly over five hours but well worth it. Spend a night or two. I stayed at the Hotel Butterfly. Three minute walk to the train station but off the main drag so it was very quiet. (Except one day. The hotel across the way was having a new roof put on and the only way to bring in the new materials and take away the old was by helicopter. ) They also have a coin operated washer and dryer in the basement for guest use. Don't let the fact that it is part of Best Western put you off. Best Western hotels in Europe are a lot different that the ones in the U.S.

From Zermatt take the train to the Berner Oberland. I stayed in Lauterbrunnen but hated my hotel so I won't suggest it. Very noisy, very uncomfortable. That surprised me because it got great reviews.

From Berner Oberland take the train to Bern. I skipped this but had originally planned to do it. From Bern to Lucerne. From Lucerne into Austria.

I've been to Innsbruck twice and there isn't much to see. It's pretty but I believe the hiking is better in Switzerland.

Wow so great to get advice from someone who has done a similar trip. After looking into Bern and Innsbruck I think we will ditch them and spend more time in the Oberland and maybe Vienna or Salzburg. Seems like a lot of great day trips from all those locations however we do not plan to have a car. Any suggestions on small group or private tours in any of the areas we are going too?