Itinerary practicality/oversight REQUESTED

When is this trip? And when do you land? Which Milan airport? I ask because if you're landing later in the day, and have delays, you may not make it that night.
How are you getting to Menaggio? Buying ferry tickets later in the day has been a fiasco with hours in line. Also take in account the rail construction - for this summer - on the Milan to Varenna route. I'm not sure if Varenna to Tirano is affected.
With a few more details, I may be able to comment is a more meaningful manner.
Have a great trip!

Thank you for your reply!

When is this trip? MAY or JUNE '26

And when do you land? Which Milan airport? MXP and arrival at 14:00 with a backup 17:30.

How are you getting to Menaggio? Train to Como -- bus from Como and no ferry required until a couple of days later when we head for the AFTERNOON Glacier Express in Tirano.

Buying ferry tickets later in the day has been a fiasco with hours in line. Also take in account the rail construction - for this summer - on the Milan to Varenna route. I'm not sure if Varenna to Tirano is affected. Thank you for the cautions!!! I will take an extra look at these! Our ferry heading to Tirano is first thing in the morning and we have two ferries to get us there in time for a sensible connection to Glacier Express.

Thanks again.... so my remaining question is the proper application of train fares. If I were younger, I'd build an engine where one would enter variables, and the system would spit out the best pass. My team created the first book-your-own air ticket, but I was so much older then. I'm younger than that now... ;-)

Most folks do fine with the half-fare card and maybe a BO Pass. If you don't want to pencil it out, the half-fare card probably will meet your needs. Do note that on the SBB app, the prices assume you already have the half-fare card. So the route prices are actually double what is indicated.

However, I chose the STP because it's so darn convenient, because you don't buy tickets- you just get on the covered train, boat, etc. and wait until the conductor checks your pass. The STP covers you up to Wengen and Murren, and then discounts after that. Once I have the STP, I find so many other, unplanned ways to use it. Just because.......

Try to push your trip into mid-June, as not all trails and lifts are open yet in early June.

Oh, for the Bernina Express, I like the regional trains better than the panoramic trains. You have so many more schedule options, no seat reservations required, trains not crowded, and the windows open, which makes for better pix and breathing that fresh mountain air. They run on the same tracks. It's an incredible experience!

I know the transportation passes are confusing, and there are several funny u-tube videos attempting to explain the options. You have time to think about it, as there's no current advantage to buying any of the passes too far in advance. I do like buying mine about a week in advance, because I like having an electronic copy, which adds easily into my Apple Wallet.

Unless you have an early morning flight, spend your last night (or more) in Lucerne. The city is charming, and it's an easy one-hour train ride directly into the Zurich airport.

Have a wonderful trip in my favorite country!

https://community.ricksteves.com/travel-forum/switzerland/fyi-panoramic-trail-maennlichen-to-kleine-scheidegg-now-open

Given you want to continue to the Bernina Railway maybe make Varenna your base on lake Como.

Between the BEX and the GEX maybe stay in Pontresina. It is a more interesting place than Chur.

Pat, thanks for your help. I completely reworked the trip, deleting the entire Como/Bernina portion because flying into Milan and doing what I had penciled in wasn't logistically feasible. We will be arriving/departing from Zurich and hitting the Appenzell area (2 nights) before heading for Luzern (3 nights) and then Lauterbrunnen (4 nights) . Your advice and some math says that we will be just fine, Half-Fare pass -- I'm now into fine tuning. My wife seems to think she must lie flat in order to sleep, so, while I'm cool with Premium Select at ONE THIRD the cost of Business Class, I am swallowing hard the airfare. She's a CPA, so I will leave that pill for HER to swallow! LMAO!!!! Non-stop Swiss Airways from Los Angeles to Zurich is $17,000. It's $4,620 R/T for the same flight, Premium Economy. What I could do with that extra TWELVE GRAND..... ;-).

Airline prices this far ahead aren't indicative of what you might get in a few months. Do your research on Google Flights. You can check price history and set up price alerts. However, always buy airline tickets directly from the airline.
LAX usually has some decent business class fares. We have flown out of LA on our last few trips. I expect you can get Lay flat business seats around $3000 each RT from LAX if you just check weekly and set up the price alerts.
Double check on Swiss if you can change the dates if you have a problem. We like British Airway, as you have some flexibility if you need to change dates, (in business.) I understand that BA is not a direct flight.
Good luck!

We typically pay around $2600/pp for premium from Nashville to Switzerland. Business class is usually $6,000-$8,000/pp for the same flight.

We’ve done premium the last 4 years. It’s a significant improvement from economy in general comfort, but we just flew over yesterday and I think I got maybe 1 hour of light sleep. I used to have hopes that upgrading my seat would make it so that I could truly sleep, but after last night I’m pretty sure good sleep on an airplane just isn’t a thing - even in the lay down beds. Unless maybe I drugged myself and then I’d be groggy the next day anyway.

The reality is that you’re not going to get great sleep on the plane and my logic is you can add multiple additional days to your trip at a spa resort for less than $17,000 to recover from 1 night of no sleep.

Also recheck your airfare periodically. Our flight in May this year to Paris from ATL suddenly went from $1800 (Main) to $695 in March after watching for months (of course had to add another $110 each for "premium" seats - basically anything not in the middle)! For Premium economy probably not so much discount. We flew Premium economy a few times but the fares now are 2-3 times MORE it seems than Main Cabin. Can't sleep much on the plane anyhow, Comfort Plus suffices. Congrats to the airlines for making us so miserable in coach that they can extract more revenue.

Wanderweg, I am right there with ya!!!! Full disclosure for all on this thread: I have never been in the tour/wholesale business, nor have I ever actually worked as a travel agent. These days, I enter an airport as if I'd never touched the profession. It's laughable. Still, I know a LOT about HOW this industry operates --- worked as a ticket/passenger service agent at United (ORD/DEN) in the 70's and later produced a "back-office" accounting system for travel agents that interfaced with the GDS (Sabre/Apollo etc.). Later, I joined a couple of startups that produced airline tickets rolling off your printer at home (dial-up AND internet). Once we had pissed off travel agents at taking away their 10% commissions on point to point air travel, I move on again to start my own company; a travel auction that provided a way for suppliers to sell excess/distressed travel inventory (airline seats, hotel rooms, cruise cabins, tours etc.). Having done that, I'm in my 70's now and, while the fundamentals of travel are the same, everything has changed! LMAO!!!!! When it comes to business travel, I know a lot about travel management tools. When it comes to leisure travel, I know a bit and understand "bulk city pairs", "consolidators", "aggregators" (I was one), and the like, but that's where it stops. I am at the mercy of the folks in Yield Management, fuel prices, and the strength of the American dollar. I am hostage to politics, world wars, and terrorism. And lastly, I know how tricky it is piecing together an air itinerary to coincide with ground transportation wishes.

For everyone providing me with advice and suggestions, thank you! I NEED IT. It is the person who claims to be a know-it-all (like the first part of this comment would seem to suggest!) who loses, and I have learned in life never to stop seeking better ways to do anything. I made a good living soing exactly THAT!

YES -- I would agree -- deal directly with the supplier, but if you DO work with an agent, grab that RECORD LOCATOR NUMBER as early as you can and compare the PNR (itinerary with the airline's reservations dept). I am astounded by the number of fraudulent sites that exist nowadays and I'd be the first to join a class action against Kayak! They should be ashamed of themselves. Even Jay Walker, who followed me in the travel auction biz (founded Priceline) would consider the behemoth Booking Holdings (owner of Priceline, Kayak, Open Table et al.) to be a joke in actually HELPING the consumer find the BEST (not necessarily the lowest) FARE/RATE. MANY of the companies listed on Kayak are GIANT BAIT AND SWITCH MARKETING retail travel agents --- they aren't even consolidators or the like. Pitiful. Sorry to get off on a tangent in this post, but todays web marketplace isn't much better than in my nascent dot com v1.0 days.

Safe travels!