Hi Yao
I like your balance of locations: water, cities and rural town (albeit Alba itself gets rather busy in truffle season)
Como: Sorry I can’t offer advice, as I’ve not been there
Alba:
The big decision will be whether to stay in Alba, or out in the wine villages around Barolo and Barbaresco. If you have a car, then I’d lean towards staying outside. The last time we went, we got into Alba early (~ 7:30am I think) and parked at the new multi-storey car park next to the train station. This was reasonably priced, convenient and also reasonably spacious, so was a good low hassle option. The advantage of doing this is it avoids the serious traffic build-up when the events are on in Alba, but also gets you into the beautiful wine country. The advantage of staying inside Alba, is that it allows you easy access to all the events that go on, and there is much to enjoy, plus the truffle market, plus a now vast outdoor street market, both with some wonderful stalls (e.g. Spezialmente and their huge range of mint related products). A special mention to catch the flag waving/throwing procession, something I always love whenever I see it in northern Italy.
For restaurants I’ve typically had much better experiences outside the headline villages of Barolo and Barbaresco, which have both delivered mixed experiences. Treiso conversely has 4 places to eat, all of which are excellent (plus I think there is an agriturismo doing meals which we haven’t yet tried). If you find yourself near Serralunga d’Alba I’d recommend Schiavenza’s restaurant. It’s inexpensive but good, plus their wines are excellent. Given the impression I got from their drive and motivation, I expect both have improved over the time since we last visited.
The tourist office in Alba is exceptional, in person and online. Use their Langheroero site as it has a wealth of info/options/booking services and call in their in person if you have the need.
Milano: A city that just didn’t click for us and we’ve not returned. It didn’t help that we felt pestered by street vendors (usually selling roses). If you like fashion, then it’s worth finding time to browse the fancy shops, plus the outlets which can have some vastly reduced clothes that are still very much current ‘season’. For the restaurants, I recall the advice to book in advance, as the better places are typically fully booked even on a week night. That’s about all I can add.
Bologna A super foody city, yet one we’ve bizarrely had few good/great experiences. Sette Tavoli on via Cartoleria is one that has been good enough for us to return to. Not fancy, just good, with a good and fairly priced wine list. We also liked a southern Italy leaning wine bar, but that shut not long after we discovered it. Luckily, we usually get an apartment there, so can graze the many excellent shops and also the good Ugo Bassi covered market. The criss-cross of older streets between the due torri and Piazza Nettuno are prime grazing ground for a food shopper (better than Eataly for sure), but there are also some good food shops on via Oberdan, but also dotted around elsewhere. Some great gelaterie as well, a few indulging my adventurous spirit with the very modern shift away from classic to creative ingredients. Enoteca Italiana is the biggest range in the city, perhaps a little bit pricey, but we’re talking 2-5% over other places rather than gouging, and for many, the convenience of the range makes up for that. Also a good place for a glass of something or a coffee. I prefer the oddly named Caffe Bazar, which has a very good range, very fair prices and listening to the staff chat to others, they came across as genuinely helpful.