8 days in Milan

Hi, you’ve selected a beautiful area to visit, and your description is perfectly aligned. I just spent a couple of weeks in June, returning to that area before moving to the Umbria region for my final week. First, I agree that you should start your locations away from Milan and end there for your flight back.

I’m not sure where you’re checking the transportation times, but each of them are longer than an hour between locations. Even getting to Bergamo - one of your shorter distances, is 45 minutes from Milan to the Bergamo train station, but it’s going to take longer to get up into the Citta Alta region where you will want to stay. Look at www.trenitalia.com for actual times (& need the Italian names):
Milan is Milano, Venice is Venezia, Mantua is Mantova, Padua is Padova.

Here’s an option. I picked Verona because it has the Roman Arena and some nice piazzas. But, I’ve stayed at all of your choices, and they would all be good options, although Mantova takes longer to travel to/from, so I would drop that option. A side note: if you’re going to move locations this often, please do yourself a favor and pack light, and be willing to get up & out of the city early to not waste precious vacation time. You will want to maximize your time out enjoying sites.
(Malpensa airport to Bergamo is 2 hours by train with one train connection. Malpensa is west of Milan.)
Days 1, 2: Bergamo. (About 2 hours to…)
Day 3, 4: Verona. (About 1.5 hours to…)
Day 5, 6: Venice. (About 2.5 hours to…)
Day 7, 8: back to Milan and fly out

I’ll go ahead and share my trip report for the June trip, if that helps.
https://community.ricksteves.com/travel-forum/trip-reports/trip-report-please-do-not-comment-until-i-change-the-title-filling-in-the-report-thanks

I like your plan--agree that I would depart on arrival and put all time in Milan at the end (one night would do it for me, but it depends on what you want to see, plus departure time). I would stick with three days for Venice.

A variation could also include a flight from Venice back to Milan and stay overnight at the airport prior to your departure. The Milan airport is about an hour or so via public transit from Milan so it is a bit of a pain to get from Milan to the airport.

Thanks for all the replies!
I should clarify that We're flying in and out of Linate, which i read was closer to the city and east of it.
Also, we're arriving in Milan Linate the Saturday evening (1830) before Easter Sunday. Would it be worthwhile to stick around for easter mass at the Duomo?
Not sure how this affects the recommendations, but thought i share.

@Jean thanks for sharing your TR. btw, we must be kindred souls because "I’m a little quirky and don’t use map tracking – just look at a map and start out." has been my MO my entire life.

Also, reading all the rich experiences you had in your 3 weeks living la dolce vita, i'm stumped at why you would ever want to come back at all...

Nabulous, well, there’s my husband and dog at home, so three weeks away is about my limit unless my husband decides to come with me for a portion of the trip! But, I do love the trip planning aspect so much, too. I have my homemade large planning calendar sheet with Post-it’s for each day across my home office desk right now with a Wales/England itinerary in the works for 2023.

Since your arrival is Saturday evening, it makes sense to spend that night in Milan. You could certainly attend mass at the Duomo the next morning if that interests you. Book a hotel near the train station (Milano Centrale) and have them hold your luggage while you go to Mass. Hotel Berna is a good choice in that location.

I would take the train to Venice on Sunday, spend 3 nights, and work my way back to Milan, visiting the other cities on the way.