Northern Italy/Lake Como ideas?

I'm not much help, but I'm also traveling to northern Italy in the spring. I'm sending a few days in Milan, and I'm considering spending a few more days in Varenna, primarily because the train goes to Varenna from Milan. I'm traveling solo, so a plane, train and ferry with all my luggage isn't too appealing. In Milan, I plan to see the cathedral and The Lord's Supper. After that, I'm open to suggestions too!

Hopefully someone will chime in for both of us.
Beth

Actually Beth the train is more doable than you think. Even though it's two of us when we travel, and despite Rick's encouragement to pack very light, we each have a medium-size rolling suitcase plus a full backpack (not a little backpack like a purse, a backpack that we carry our purses/ipads etc. in when we're on planes and trains and we wear it to the side of us so no one can access it without our knowing it).

With those two things (but not a huge rolling suitcase, a medium one), It's not really a struggle to get on and off the trains and stash the suitcase on the train when you get on. Usually if it needs to go overhead someone will offer to help. And the ferry is easy. We took it to and from Bellagio with our luggage and it's no problem to walk onto it pulling a suitcase. We actually enjoy the train travel as part of the Europe experience, even on our longest leg last time from Milan to La Spezia last time. There's no doubt it's tiring but we saw plenty of lovely scenery and train travel always an interesting insight into Italian culture. And even if I'd been a solo 60-year-old instead of along with my daughter, I wouldn't have felt unsafe at any point in our train travels in Italy.

Visiting The Last Supper makes a trip to Milan worth it IMO. Wandering the central area is enjoyable and the Duomo is beautiful and impressive to tour. We stayed in Varenna when at Lake Como and it was delightful.

What about Bolzano where you can see Otzi the Iceman and then take a bus to Ortisei to see so e of the Dolomites. About a 3 hour trip from Milan or it could be on the way down from Switzerland.

While I have yet to visit Verona, it seems like a wonderful option as well.

If Switzerland is first on your itinerary, you could take the train to Varenna via the scenic Bernina Pass route rather than approaching from Milan. There is a named scenic train that plies the route, or you could take a regular regional train on the same tracks. You would ride the train as far as Tirano on the Swiss-Italy border, and transfer there to an Italian regional train for the short trip to Varenna.

This is the only cross-border train from Switzerland into Italy that goes over the Alps instead of under them in a tunnel. (There is one other scenic route, the boat train combo named, the Gotthard Panorama Express, from Luzern to Lugano that has a shorter, higher tunnel than others, and is also quite scenic, if this fits your Switzerland itinerary better).

https://www.rhb.ch/en/panoramic-trains/bernina-express

https://www.sbb.ch/en/leisure-holidays/travel-in-switzerland/panoramareisen/gotthard-panorama-express.html

After Varenna, you pretty much need to head to Milan to get a train to other towns in northern Italy. But there are endless options there, within say 2 hours of Milan:

Direct trains with no changes: Parma, 47 minutes; Torino, 48 minutes; Desanzano sul Garda/Sirmione, 50 minutes (on Lago di Garda with Roman sites); Verona, 1 hour 13 minutes; Bologna, 1 hour 14 minutes; Modena, also 1 hour 14 minutes.

Lots more possibilities if you make one change, such as Asti, 2 hours with a change at Torino.

Any of these would be great if you want a smaller city than Milan. And some might be having food-oriented festivals in September, which could be fun.

Lola, thank you so much for all of that detail! I'm just starting on our plans and haven't yet figured out if we are starting out in Italy or Switzerland but either way taking the Bernina Pass route either from or to Varenna has been on our list ever since we decided on Switzerland along with Italy. It looks amazing! We use travel points mostly for our flights and a lot of our lodging so figuring out how to maximize the points value as far as where we fly in and out of adds a little complexity to the planning. Like it actually might make the most sense for us to fly into FCO and take a train to Milan and start from there, rather than flying into Milan or into Zurich from the east coast. We want to spend our time in Switzerland exploring the Lauterbrunnen valley but that's as far as I've gotten. But that's a question for another thread once I start getting my ducks in a row. But all of those towns and the links are so extremely helpful, thanks again!

Both Milan and (especially) Turin have a lot of Art Nouveau architecture, if that happens to be of interest. The Galleria Vittorio Emanuele II, near the Duomo, is worth seeing; I'm sure the shopping is expensive.

Padua has a lot to see; the Scrovegni Chapel is the #1 sight there (buy ticket in advance), but there's a lot more. It's also a good base for seeing Vicenza and Ferrara. If you have any unfinished business in Venice, that would be a super-quick train hop from Padua. Then you have Verona, also on the rail line between Milan and Padua; it's where you switch trains to get to the western part of the Dolomites. Rick covers Padua, Vicenza, Verona and the western Dolomites in his guide to Italy.

I also like Bergamo, a hill-town on a secondary rail line east of Milan.

I'd expect the Dolomites to be very nice in September. In addition to the mountain villages, there are some attractive towns down in the valley along the rail line: Bolzano, Bressanone, Chiusa/Klausen, Merano, etc. I'm not sure about September, but in the middle of the summer air conditioning is often needed in the area if you aren't staying at altitude. Not all lodgings have it, so that's something to check out.