Help planning trip from Tuscany to Swiss Alps

Billie, A few background questions.

• Where are you flying into?
• Is this where you will pick up the car?
• Where are you flying out of, same place, or possibly Zürich to avoid doubling back?
• Are you considering driving into Switzerland, or train?
• How are you about driving over spectacular passes? Would that be a highlight or a horror?
• Be aware, hiring a car in one country (Italy) and returning it in a different one (Switzerland) is very costly; they have to drive the car back. Driving to Switzerland and returning back to Italy is no issue.

Snowy mountains are unlikely to be Lake Maggiore in September, you need to go higher (into Switzerland) for that.

One obvious choice is Zermatt. Relatively easy to get to be train from Italy. It is car-free (park further down the valley and get a train in. Afterwards you can get a train to Zürich airport.

Another choice is Berner Oberland. One of Mürren, Lauterbrunnen, Wengen or Grindelwald. Mürren and Wengen are also car-free. Longer and more difficult route by car, not much longer by train.
Info and hotels: https://jungfrauregion.swiss/en/summer/

As for driving over passes. One route to the Berner Oberland is over the Nufenenpass and Grimselpass. Go to Youtube and search for both names

Lake Maggiore is in Italy, near Milan. You want to stay in Switzerland, in the Berner Oberland where the Switzerland your husband dreams about exists.
Grindelwald, Wengen and Mürren are in the mountains offering spectacular views.
If you have an Italian rental car you will want to return in Italy to avoid huge drop off fees in another country. We used Milan MXP to pick up and drop off car that we drove in Switzerland.
We also visited the Italian Lakes, Lake Maggiore when heading north, and Lake Como on our way south. When entering Switzerland you need to a vignette for your Italian rental car. We stopped at the first gas station or convenience store we saw.

Chris,

I guess I don’t know what I don’t know. Lol!

Where are you flying into?
I was considering flying into Florence for the proximity to Tuscany. I could do one way and fly home from Switzerland so I don’t have to back track but I also don’t know what would be best.
Is this where you will pick up the car?
We would pick up the car in Florence. I guess we could drive it to Milan and drop it off?
Where are you flying out of, same place, or possibly Zürich to avoid doubling back?
It’s a consideration.
Are you considering driving into Switzerland, or train?
I’m thinking train may be best. Do you have recommendations for scenic trains?
How are you about driving over spectacular passes?
Not too sure about this! I’d love to be able to stop and get pictures though.

Suki,
My mistake. I thought I saw on the map that lake Maggiore extended into Switzerland! Thank you for the recommendations!

Billie, thanks for feedback. The more info you put in a question, the better answer you get.

Plan A (train) - dump car in Milan, train from Milan to the Jungfrau Region part of Berner Oberland (one of 4 places I listed above, see https://jungfrauregion.swiss/en/summer/ ).
Look up train times on SBB (Swiss Federal Railways) website: https://www.sbb.ch/en
Enter Milano Centrale to Mürren, Lauterbrunnen, Wengen or Grindelwald (whichever you choose), and a date and time.
You will see snowtops on the way, and plenty more in the Jungfrau Region.
Afterwards train to Zürich airport ("Zürich Flughafen" is the name of the station).

Some photos (click): (1) Lauterbrunnen. In the valley bottom, end of the road.
(2) Train climbing up to Wengen. Lauterbrunnen is down below. Mürren is on the other side of the valley, on top of the cliffs. You need a cable car to get up there.

Plan A½) Zermatt. Less train from Milan, more train to Zürich airport. Or could fly back out of Geneva, if flights better.

Plan B (car). That restricts it to Lauterbrunnen or Grindelwald; the rest are car free, your car would sit in paid parking. If you are spending your days up in the hills, it would not be used anyway.
This means you can go "over the top" via Nufenen and Grimsel passes.
Return to Milan to dump car and fly out.

The advantage of plan B is driving over the passes (did you look up videos on YouTube?). Otherwise choose train and fly back from Zürich.

And the top 1/3 of Lake Maggiore is in Switzerland, bottom 2/3 in Italy.

Chris,

Thank you! This is so helpful. I did look up the views and while beautiful, I think the train may be less stressful overall. I’m not sure how much it would be but it sounds expensive to leave the car in Switzerland and I don’t think I’d want to trek back to Milan to drop it off. How is the transportation between villages/cities? Are taxis widely available? We didn’t have a car our entire two weeks in Italy and relied on taxis and private drivers.

Billie,
Transportation in Switzerland between villages and towns and even trailheads for hiking is exceptional! Buses, trains, and trains connect seamlessly and efficiently. We never rent a car anywhere in Switzerland and we go every year. Rick Steves’ Switzerland guidebook, especially the section on the Berner Oberland is highly recommended. For an activity-filled week, get an apartment in Wengen, Lauterbrunnen, or Mürren and settle in, enjoying light hiking, day trips, and amazing scenery. Fly out of Zurich as Chris suggests.

How is the transportation between villages/cities? Are taxis widely available?

Taxis? Aaaarghh no! The roads end, and taxis are VERY expensive in Switzerland. I have a Swiss salary and I can't afford Swiss taxis!
Trains and cable cars go where roads do not, transport you between villages and up mountains to the hikes, and to the very summits.

Click here for a "map" of the Jungfrau Region. Red are rail lines and black are cable cars. Interlaken is between the lakes at the bottom, Lauterbrunnen is in the middle, Wengen to the left (compare with photo I posted last time), and Mürren to the right. Grindelwald way to the left i the next valley. There are also buses filling in the gaps between the trains.

Thanks guys! Sounds like the Swiss have this transportation thing figured out!

Billie, the Swiss transportation system is amazing! Yes, they have it all thought out. It is not cheap, but it is extremely efficient and pleasant. Depending on your final plan, you will want to look at passes.