My serious answer is going on a cruise. I've been pretty vocal here about how I dislike the idea of cruises for multiple reasons. Mainly, I see absolutely no advantage to a cruise over just directly visiting whatever destination it is you're going to. No forced schedules. Better food options, no norovirus, etc.
I am certainly not a cruise guy and have only ever done one (Disney cruise with the kids) and I heavily prefer just hanging at an all-inclusive, but I think the obvious answer here is when "whatever destination you're going to" is multiple places.
Viking cruise, Alaskan cruise, etc. But even the mention of all-inclusives above isn't a fair one as a lot of Caribbean cruises are sooooo friggin cheap they're just in a different price range. If I lived in Florida and could just hop on one without flights it probably would've happened by now with some of the ridiculous offers they throw out there.