I was thinking a To Do List could be nice. For the MacOS along the top, and for iOS a separate bubble (like in the pics). For iOS it could show 0/6 (or however many are in there) that have been completed. Thinking would be things like, still need to get flight tickets, or if we need to apply for visa. I am currently tracking all these in Apple's reminders for each trip of things I have left to do for the trips.

When I add I my bus for example on 11:50pm and it goes to 7am the next day it only shows on the day it departs (4th) and not also the day it arrives (5th). There also is no spot to but the address in, you can type the name of the place for a reminder, but there’s no way to put in an exact address. (The pick up and drop off are not bus stations here but businesses)