Totally get that, and it reminds me of an article about how planning builds a different kind of memory. The_sarah is right about earning the miles, but I'd say you earn the map in your head first, you know? That old-school work makes you feel the place before you even get there.
I used to just book flights and hotels online, no real planning. But last year I spent like two weeks reading up on Lisbon before going, and it made the trip feel totally different. I mean I already knew the street names and where to find the good coffee spots. It felt like I had been there before, idk.