Como or Lugano? Alba or Barolo?

Milan has two airports. If you land at Milan Malpensa (MXP) I would suggest you visit nearby Lake Maggiore (Stresa is a nice town from which you can visit the islands). The northernmost tip of the lake is part of Switzerland so you could take a day trip there as well. I recommend Lake Maggiore especially considering you plan to visit Piedmont (the western shore is in Piedmont) and Malpensa is there.
If you absolutely must go back to lake Como, then if you stay in Menaggio, on the western shore, you are a very short distance from Lugano (40 min). I usually stay in Menaggio and visit Lugano from there (Lugano’s prices are double).

Regarding Barolo or Alba, either one is good. Barolo is a smaller village, Alba a bigger town but with a quaint historical center. But they are only 15-20 min apart so you can visit both from one place.
It depends on whether you like wine or truffles more. If you like both equally then you could find an Agriturismo between the two. There are more the one among those vineyards I’m sure.

I think Stresa is the better choice as well. It has pretty much the same attraction as Lugano without a border crossing. You can take a chairlift up the nearby mountain and hike down, you can visit Isola Bella and enjoy lake views, all while you adjust time zones. Barolo is quite small and there's not a whole lot to do. Alba has many choices and has a lot of energy. While Alba gets a lot of visitors, it still has retained its own considerable character. For a nice little city that gets fewer tourists, we used Bra as a base - enjoyable especially if you like architecture. Look at this article: https://www.apathtolunch.com/2015/12/an-italian-itinerary-small-cities-in.html

I’d like to add that Lake Maggiore has a lot to offer to the visitor: Stresa, Borromean Islands, Cannobio, Locarno (CH), Orta San Giulio on nearby lake Orta, Centovalli scenic railway, etc. All of these vacant be visited from Stresa.

Therefore, given the plethora of great things to see, you will feel cheated if you stay only 2 nights. If you have the vacation days, see if you can stay 4 nights in Stresa.

Official tourist websites
http://www.illagomaggiore.com/en_US/home
http://www.stresaturismo.it/default.asp?newlingua=UK

Ferry timetables below
http://www.navigazionelaghi.it/eng/m_illago.html

I should have perhaps made my question a bit clearer. We will be staying in the Lake Maggiore/Stresa area as well as Orta and Turin. I am just trying to decide which locations on a couple of the stops Thanks so much!

Chris,

Of the two choices, I'd suggest Lugano. I'm not sure if there's an Agroturismo in that a area though. I'd suggest staying in Lugano, so that you'll be in walking distance of the sights. I've stayed in Hotel Pestalozzi and would certainly recommend it.

As you'll be driving, I imagine you're aware of the need for each driver listed on the rental form to have the compulsory IDP. Also, I don't know if the route to Lugano uses any motorways, but you may need the Swiss Highway Tax vignette.

Rick does have a short description on Lugano in the Switzerland guidebook. You might get some other touring ideas from this website - https://www.myswitzerland.com/en-ca/lugano.html . You could take a trip to Monte San Salvatore or Monte Brè, to get some great views. There's also a Casino there if you're interested.

If Lake Maggiore is already in your plans, then Menaggio on lake Como or Lugano.
As I mentioned Menaggio and Lugano are a very short distance away by car. So it depends if you want to see lake Como again or just see Lugano.