Are tours ever longer that a few days, or ever more than a few hotel stays? I quick thought would be separate checkbox columns for each stop. Not my preferred method, but quick and dirty.
Otherwise I’d maybe try to incorporate one of these methods or some form of it that uses a date instead of a unique ID. If you only need the checklist for a short period of time or for the day, then you could probably do something with a date and when the date changes, the list would automatically reset.