I just found out the my sister-in-law is getting married in Milan, Italy over Labor Day weekend. DS will turn 4 just a few weeks after that.

It's still a long way away, but I'm excited and ready to plan! Any advice on traveling that far with an almost 4 year old? Bonus if you have any recommendations of family-friendly things in Milan!

----- (my brain dump of current plans is below, if anyone actually wants to keep reading) -----

Timing: we plan to shift our travel so we arrive 3-4 days early and then leave a day or two after the wedding...so that we have maximum time to adjust to the new time zones before the wedding itself. What fun things should we do during this time? And any tips on how to adjust my almost-4yo to the new time zone? We will be arriving at 10:30 local time, and he will be exhausted but excited.

Travel: we basically have 2 options,
home -> NYC -> Milan
home -> Rome -> Milan
NYC is a shorter flight first with a layover late afternoon, and then takeoff right around dinner time. We could all hopefully get ~6 hours of sleep before landing in Milan.
Rome is the long flight first. Even if it is overnight (I don't think it is), I think that doing a layover in Italy with a tired/grumpy toddler and then having to get on a second plane for just an hour is going to be significantly more miserable. Either way, it will still take another hour to get from the Milan airport to our apartment/hotel/wherever we stay....it is almost 24 hours door to door.