Swiss train/lodging help needed

You can see 2nd-class train ticket prices on Rick's Italy and Switzerland cost maps. Using that method, the ticket cost estimate adds up to a maximum of about $35 per person within Italy and $255 within Switzerland. There is not a Swiss pass that particularly saves money for that route. You can buy the Glacier Express ticket in advance for the actual price of 145 Swiss Francs in 2nd class, and buy the Italian tickets in train stations there. For train schedules from Milan to Tirano, en-route to St. Moritz (or Pontresina), see www.trenord.it. Booking hotels ahead is the best way to be confident that you have a place to sleep.

The RS estimate maps are pretty iffy. The fare from Milan to Tirano is 11.05 euro ($15). Tirano to Pontresina can be done on the Bernina Express which has panorama cars (you might have to go to 1st class for that) or a regular train (same scenery). That one is 27 chf ($30). Next day the Glacier Express leaves from Samedan, which is a 5 minute train ride away. You could save a few coins by getting off at Brig and taking the next train back to Milan. The run up to Zermatt is in a rather narrow valley and you really cannot see the spectacular mountain peaks all around you. You will not see the Matterhorn until you get off in Zermatt. If you want to stay in Zermatt, there are plenty of hotels there, and since they have skiing all year round, there will be some open and probably at good prices. From there, ride up on the Gornergratbahn to really get a good look at the mountains (if the weather is clear).
If you do stay on the train to Zermatt, your total train ticket costs will justify buying the 1-month Half Fare Card for 120 chf.

OR...if you don't want to spend your vacation sitting on a train looking at all the scenery pass you by - you could spend as little as 4 hours on the train and end up in one of the most beautiful places in Switzerland and some would even call it one of the most beautiful places on earth. Lauterbrunnen is situated in a valley looking up to the towering massive Swiss Alps all around you. Little alpine villages (Murren, Gimmelwald, Wengen) on either side of the valley (only accessible by train/gondola) host very nice hotels and restaurants and eye-popping scenery. You can go for a walk, a hike, whatever you please, but mostly you'll be wondering how such a beautiful can even exist. It's the place I would choose over Zermatt and DEFINITELY over sitting on a slow moving train.

Ditto Sam's routing. The trip from Milano-Centrale to Tirano will take 2hrs30min. Fare is 11.05Euro. The train runs every two hours beginning at 06:20. At Tirano, you change to the Bernina Express with a destination of Pontresina. The Bernina Express does not go to St. Moritz - it goes to Chur. Pontresina is much more scenic than Chur. If you select St. Moritz as your destination, you won't be on the BE. Most likely you will be on a different regional train. If your destination must be St. Moritz, take the BE to Pontresina and transfer to a different regional train to go to St. Moritz. This is a 12-minute ride. No need for advance reservations. Just buy the ticket and get on the next train.

The next day, you can board the Glacier Express at either St. Moritz at 9:02 or at Samedan at 9:17. Journey time to Zermatt is about 8:00hrs. The fare I see is 72CHF from Samedan to Zermatt via Disentis and Andermatt. You will arrive at 17:00 or 5:00pm. Or, as Sam indicates, you can get off at Brig and take the train back to Milan. Major north/south fast trains stop at Brig. Train arrives in Brig about 15:20. Or, spend the night in Zermatt and see the Matterhorn in the early morning before the clouds all roll in. Then, it's a 4.0hr journey back to Milan on a regional train back to Brig where you transfer to a fast train back to Milan. Fare is about 80CHF. Hope all of this is not too confusing.