Overwhelmed planning 2 week trip to Milan and environs beginning on Monday, 9/29/25!

Are you looking for day trips only or also for multi-day excursions during the week? The lakes are an easy day trip, but CT is too far to return in same day. You can be to Turin in an hour.
You could pick up a Lombardy book, like The Blue Guide, for a comprehensive list.
See also: https://www.in-lombardia.it/en

Bologna and environs, Verona , Bergamo, Brescia and many others are all within day trip distance
Stresa on Lake Maggiore, Lake Garda

What to see and do in MIlan- under At a Glance
Monumental Cemetery would be a great photo opportunity- closed Mondays I believe.

https://www.ricksteves.com/europe/italy/milan

Bergamo, Brescia, Monza, Pavia

If I'm Googling correctly, you can get to Turin in as little as 45 minutes by train. You might want to wait for your husband to be available, as there is a wonderful cinema museum there, along with lots of other things to see and do (original Eataly, Fiat factory with rooftop test track, cool car museum, probably some more adult sights--I was there with a 12yoa boy, so...). It's a nice city.

From Milan, we have enjoyed day trips to:
-Lago di Como- we took the train to Como and then a ferry to Bellagio, which was lovely
-Lago Maggiore- we took the train to Stresa and then a boat to/around the Borromean islands, which was also lovely
-Lago di Garda- we took the train to Desenzano del Garda and included a boat ride to Sirmione

I wouldn't say any of these are off the beaten path at all but we had a wonderful time at each of them and they were very easy to get to on public transport from Milan. Good luck with your planning!

I suggest you have a look at Bella Milano Tours. It is a small company and the tours are interesting. Such as a high-fashion tour, a Stanley Tucci food tour, if you read Beneath a Scarlett Sky there is a tour focused on that book as well. We had a wonderful, wonderful guide.

I 2nd Brescia!
We were just there 3 weeks ago. We went specifically for the arms and armor museum as we were traveling with our two sons.

It's a short walk (or I'm sure a bus or taxi) from the train to the old city. Fun restaurants and shops (although I didn't go in any). The museums they have are top notch! It's a lovely easy walk between all of them. The history museums was in depth and so vast. Honestly you could spend a whole day just in that one. We had one full day there (2 nights). While we did 4 of the museums, my husband and I could have easily spent more time in two of them.

It would be a great day trip!

A poster above mentioned Monza in passing, but I wanted to highlight it. We spent 4 months there a few years back and really enjoyed it. The historic town centre is pretty and lively. The royal and urban parks are huge - so big that while we lived at one end of the park, we could not hear cars on the Formula 1 racetrack at the other end of it. And they're gorgeous, so fun to walk and walk and walk through. It's just barely northeast of Milan. It's a one or two stop train trip, depending on which train you get on. There's a pretty rose garden next to the small palace, both worth a look.

Monza would be a great day out on your own.