Trip to Northern Italy / Switzerland

Lodging around Lake Como is tough during the busy season, and Varenna doesn't have a lot of options to begin with. Start looking now, because availability of a nice place may determine what dates you can be in Varenna. (I struggled to find something in the mid-lake area for September.)

I've consistently read that St. Moritz is a fine place to go skiing but is otherwise not very attractive. Pontresina is said to be prettier. I think lodging may be tough in that area, as well.

I am sure you will get several suggestions but here are a few thoughts on your proposal. Have you been to Milan before? If not I would allow 2 full days to see the highlights. I would spend more time in the other areas you are considering. The lake como area is very nice. We spent 4 nights there last fall and felt we got to see a good portion of the important sites. What is your budget for hotels? There is an awesome hotel in Cadenabbia area (actually Tremezzo) called the Grand Hotel Tremezzo. We met a couple that did a spa day there and they said it was awesome but it is very expensive. Since its you honeymoon this may be worth a splurge. We stayed outside of Bellagio, but would stay elsewhere if we returned. We did the Bernia express from St. Moritz to Lugano. I like your plan to start from Tirano and end in the St. Moritz area. I would suggest Pontresina over St. Moritz. St. Moritz itself is not that great IMHO. We stayed two nights there. The lake was nice and we took the cable car/funicular to Piz Nair in the afternoon. It was very pleasant and fortunately free as our hotel provided us with a local transportation card. I think Pontresina has some nice hotels and is more quaint. I saw a recent thread in the Switzerland forum looking for hotel suggestions. I have not been to Lucern since my own honeymoon decades ago so I am sure you will get some suggestions there. There are several discussions about Lucerne as well. I do suggest you book soon as you are going in peak season and I know we booked for October in May last year and had some issues finding accommodations particularly in the Lake Como area. You definitely want to train to Lucerne. The Swiss train system is wonderful, efficient, and punctual.

We traveled to Switzerland (first time!) last September. We flew to Zurich and then took the train to the Berner Oberland via Interlaken and stayed a week in Wengen. It was like being in heaven. I cannot recommend it enough. I actually gathered all of the destination advice and recommendations from this forum. The BO is loaded with hiking, lakes, food and unbelievable views. We took day trips each day. At the end of the week we took the Bernina to northern Italy and continued with our 3 week vacation. Feel free to message me for details.

thank you all so much for the tips! super helpful :)
I will comment back when we have more solid of a plan to let you know where we ended up and hopefully help others!

train or drive to Lucerne?
spend a few nights here? fly back to NY from Zurich

Definitely train. The fastest way is through Thalwil, but a bit longer and more scenic is via Chur, and Pfaeffikon in 5 1/3 hours, 1 hour longer via Thalwil, mainly because of 45 minute change time in Pfaeffikon waiting for the Voralpen Express.

I suggest you leave the Bernina Express train at Pontresina, the mountain town just before you reach St. Moritz. Most people prefer it to glitzy St. Moritz. there are several lifts you can take up to mountain tops right from Pontresina, such as Muottas Muragl and Alp Languard.

https://www.chesa-mulin.ch/en/

https://www.pontresina.ch/en/experiences/mountains-and-railways/alp-languard-muottas-muragl/opening-hours-an-rates-summer/#

https://www.myswitzerland.com/en-us/experiences/muottas-muragl-a-front-row-seat/

A two-night stay at most Pontresina hotels will come with a card for free local transport, including the mountain railways. Also you would be able to visit St. Moritz by train for free, if you are curious about this famous resort town. Here is the offer on the Chesa Mulin webpage:

Free use of public transport throughout the Upper Engadine (from 2 nights, valid for Engadin Bus and Rhaetian Railway)
Sun loungers on the terrace
Ski pass for CHF 47.- per person per day (from 2 nights, for the duration of your stay)
Use of all mountain railways in summer (from 2 nights, for the duration of your stay)

Edit: I now see that Kim already suggested Pontresina instead of St. Moritz. So this is an endorsement of that suggestion.

Hi all. Thank you all so much for the great suggestions...

Here is where we landed, and we made a lot of the decisions based on your responses and research that came from it:

~ Flying into Milan, spending a few nights there.
~ From there we head to Varenna for a few nights.
~ From there, we will take the Bernina Express through Tirano to Pontresina where we will spend a few nights and explore the area.
~ Then, we're heading to Zurich for a few nights and flying back to NY from Zurich

All in all it's a 2 week trip!

If anyone has any suggestions for places to eat or explore, things to do (tourist attractions, hole in the wall, etc!) we are all ears.

Lastly, does anyone have any knowledge on how to travel from Pontresina to Zurich? We plan to travel by train, and based on previous responses I know it is very do-able and should be easy - just haven't looked into it yet so any tips would be great :)

Thank you again for all of your help. We're so excited ..

Start booking hotels now. St.Moritz is underwhelming. Skip and head straight to Lucerne. Use the extra days in Lucerne to discover the region by car or train.

https://www.sbb.ch/en/buying/pages/fahrplan/fahrplan.xhtml, is the Swiss rail site, but also includes boats, buses, mountain lifts, local transport. Just put in the start point, end point, date and preferred departure time and, voila, you got it. You can fine tune the route in the "via" button, and "advanced search" button. The site always shows the fastest route, but you can adjust to take a more scenic route.

In your case, start is Pontresina, end is Zurich HB (main station). However, per your original plan and the previous poster, Luzern would be a better location to spend your last few days. Its is only 1 hour to Zurich Flughafen (airport) from Luzern and trains start running around 5 am.

Lucerne is pretty nice! I don't think you'll miss the St. Moritz area if you spent extra time in Lucerne. Or Lucerne then the BO, Swiss heavyweight champion of flogging tourist with surreal mountain majesty.

The topic of Varenna and other places on Lake Como comes up here very often. You can find some good ideas, including both sightseeing and restaurant suggestions, in earlier threads. I used the Search function to get these results from the last two years:

https://search.ricksteves.com/?button=&date_range=2y&filter=Travel+Forum&query=como&utf8=%E2%9C%93

The results aren't in chronological order, so pay attention to dates if you're looking for logistical details.

I found few rooms available in the mid-lake area (where Varenna is located) a couple of weeks ago when I was trying to book a room in late August. I'm afraid you will have some difficulty. Take care of that immediately.

Newbie here. Does anyone know if the high speed or other train from Milan to Interlocken via Spiez stops in Stresa on Maggiori. We are coming from Lake Garda. We need to know if we have to Start in Milan or if we can get on in Stresa. We need to be in Interlocken on August 20th so much of our plans revolve on this.

Yes there will be trains. Go to www.sbb.ch

Because it is beyond June 9, many Italian trains are not showing on the schedule. Add to that is the fact that the main rail line will be shut down between Arona and Stresa this summer after June 9. There will be rail replacement buses to cover the gap.

So just be patient. By early June, everything will be clear.

Is there any way you can spend time IN the Alps, Wengen or Murren? You don't need time in Zurich, unless you have an early flight out. It's so easy to get to the Zurich airport from Bern or Lucerne.
And if I had to chose between nights in Milan or Wengen/Murren, I'd choose the latter hands down!
Safe travels!