Milan or Stresa?

My boyfriend and I have 8 days in Switzerland and Italy in late August. (Flying into Zurich and out of Milan-Malpensa.) We have decided to spend 5 days in Switzerland and then take the train from Bernese Oberland to Stresa, spend 1 night in Stresa, and then take the train to Milan and spend 2 nights in Milan. (We also looked at Lake Como but it seemed like too much of a detour from on the way to Milan). We are not sure if this plan is the best option and would like your advice.

Question: which one should we do:
1. Bernese Oberland -> 1 night in Stresa -> 2 nights in Milan (original plan)
2. Bernese Oberland -> 2 night in Stresa -> 1 nights in Milan
3. Bernese Oberland -> 3 nights in Milan (skip stresa)
4. Bernese Oberland -> 3 nights in Stresa (skip milan)
5. Some other option??

I am asking because I have heard both good and bad things about Milan.

About me: I am not interested in fine art but I am interested in architecture. I like cities but I also like being in nature/outdoors. And I LOVE Italian food!

Where will you stay in the Bernese highlands?

One night anywhere is pretty useless: travel in, unpack, eat, sleep, pack, leave. Two nights will give you at least one full day to explore a place, three nights will give you two full days. So which would you prefer -- exploring a lake or exploring a city for a couple of days?

Regarding Italian food: there are wide varieties in the styles across the many regions. And typically, restaurants have quite limited menus that focus on local preferences. Bigger cities have a wider choice of restaurants with cuisines from other regions.

You cannot compare one is a big city, which to me is an interesting city but unfortunately cannot compare with the great Italian cities, in other countries it would still be seen as great place to visit.

Stresa meanwhile is town on a lake, a lovely town to spend time in but very different.

Stresa can come across as, how can I put it? Maybe staid in a somewhat-sterile upmarket kind of way. Isola Bella is there and it is attractive. For us however, the Eremo S. Caterina del Sasso was the star of the lake---we went twice. Milan, as Richiavo has said, is an urban experience. Not our scene, but that's just our opinion.
MF makes a good point about the relative value of one-night visits. For example, if it rained in your fave place(s), and you were only there for one night...
I am done. The umbrella.

You're always going to find people saying good and bad things about Milan, and many other places. You won't find a definitive answer here or anywhere else, so go and find out for yourself. I love Milan, but I also love museums and quirky neighborhoods, both of which Milan excels at.

I also love Stresa and have visited many times. I wouldn't ever bother going for one night, though. I don't go anywhere for one night - the effort is never worth it.

Loving Italian food isn't telling much, as there are a thousand and one types of it, depending on the region, the time of year, and of course the talents of the chef. Milan has great restaurants - and it has Peck, probably oneof the world's most outlandishly fabulous food emporiums. Stresa has a few gems, too, particularly if you're fond of freshwater fish.

All depends oon the number of museums you plan to visit in Milan. Milan can usually be visited in a day trip from Stresa, may be by train Stresa dp 8.40 - Milan ar 9.37, Milan dp 21.29 - Stresa ar 22.37

What if we did: Bernese Oberland -> 3 nights in Milan (skip night in stresa)
And on one of the days in Milan, day trip to Stresa or Varenna?
Does it make more sense to do a day trip than one night?

Perfectly feasible if you like to do the Stresa - Milan leg 4times (and to pay for these 2 RT journeys).

Go to Varenna. There are regular services between Milan and Varenna, the journey from station to station is just one hour and three minutes, and the fare is a flat 6.70€ each way way. Easy.

And the sunsets are better in Varenna. Find a terrace with a view of the lake to enjoy a drink at sunset, then take the train back to Milan.

In defense of Milan, my wife and I were there for 4 nights recently, partly for a work convention. Nearly everyone I spoke to urged me not to spend much time there but I loved that city, had a great time, and would be glad to return. There's not too much in the way of historic sights but there are a lot of interesting modern buildings on the north side and the by the canals on south side, where we stayed, there was tons of street life at night and literally hundreds of restaurants. We had fantastic food in Milan and enjoyed wandering the city. I cycled around one day and that was great too.

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