Technically challenging 3hr to 6hr flights, with stunning views along the way from 5000-15000ft, to interesting places which would take days to drive to. Then, after a couple of days checking out the place and all the coffee bars and the food etc, do the same thing to another interesting place.
Preferably in the southerly direction. I rarely fly north; the temperature drops as you go and I don't like that
It makes for great though unusual holidays. You get to see a lot, you are not tied to dates on 737 tickets; in fact most of it would be very awkward using commercial travel.
You are tied to the weather charts a bit but not as much as if you had to fly VFR
