Hi all,
I got some some help here when we were planning our trip, so thought I'd pass on some things that might help others. We're a White couple in our 50s/60s who've never been to Italy before, for context.
We flew from the West Coast US to Milan Malpensia. Spent one night in Milan, train to Pettanesco on Lake Orta for two nights, taxi/walk to Stresa on Lake Maggiore for 2 nights, then ferry to Cannero Riveria on Lake Maggiore for 3 nights. Taxi/bus back to MXP on departure. All of of travel except for Milan was arranged by Inntravel. We did a ton of walking/hiking (on purpose).
Transportation. At MXP it was much faster and easier to buy the express train tickets from inside the ticket station than at the vending machines. Weird but true. In Milan we walked or used BikeMi bikeshare (we're bike commuters at home, so it was much easier for us than figuring out the Metro). The protected bikeway system was superb and bikeshare was really affordable and easy to use. We weren't 100% sure we were on the correct train leaving Milan Centrale (no announcement and no ticket check) but we were -- big contrast between that regional train and our transfer to another regional train to get to Lake Orta. The ferry system on both lakes was super easy to use and understand. We did some one-way hikes with return on the ferries on a few days (about 5 Euro for a one-way ticket back each time).
Departing MXP -- make sure you allow plenty of time for all the walking you'll need to do if you're flying direct back to the US! The US-based gates were WAAAAAY at one end of the airport from where the bus dropped us off and also WAAAAY far from security. It took us at least an hour from drop off to check in to through security due simply to all the walking from one end to the other.
Lodging. In Milan we stayed at the Hotel Bagliori, about a 10 minute walk from Centrale Stazione.
Money - the only places that were cash only were the ferry terminals. We pulled out 100 Euro at a bank in Milan and only used about half of it -- the rest was all card nearly everywhere, even the small markets.
Safety -- I could see that if you were going to get pick-pocketed, Centrale Stazione would be the place :). It was packed and lots of folks who were looking for opportunity. But it was fine. No concerns anywhere else at all.
Crowds - other than the train station, Milan wasn't any more busy than I'd expect a large city to be. We went to the Duomo in the late afternoon and it was lovely and not very busy. We went to Sforza Castle Friday morning and there were tons of school kids there on field trips, but nothing different from what you'd see at home at a place like that. The small towns on Lake Orta and Maggiore were really busy on Saturday and Sunday (streets were literally packed), but with day trippers. They were beautiful weather days and it totally made sense. On Monday wet weather rolled in and the number of people dropped by 2/3.
Weather. The first 3 days were sunny and in the 70s. Perfect. Then the wet rolled in (the same system that was flooding just a little bit to our East :(). Luckily it only rained really hard at night (which I think is the normal weather pattern) and the daytime highs were in the upper 60s, which was perfect for all the hiking we did. So we didn't get the glorious sunny pictures, but we didn't get rained out either. And the gardens were gorgeous and in full bloom!
Language. I spend the last 6 months doing Duolingo everyday and it really did help in being able to understand the gist of most things, read the important signs, etc. My ability to speak was at a 2 year old level, but I could count and point :).
Happy to answer specific questions if folks have them.
Carrie