I plan trips the same way I plan a media budget

Every trip gets the same brief a campaign would: a hard budget ceiling, one or two non-negotiable quality floors (a decent hotel, food that isn’t an afterthought), and everything else — itinerary, pacing, which sights make the cut — left flexible enough to change once I’m actually there.

The ceiling matters more than people expect. Without one, “we’ll figure it out” quietly becomes the most expensive plan in the room, the same way an uncapped test budget quietly becomes the whole quarter’s spend. A floor matters just as much — cutting the wrong corner (a bad hotel, a rushed final day) doesn’t save enough to be worth what it costs the actual trip.

What’s left after the ceiling and floor is where the trip actually gets designed: timing to dodge a holiday surge, picking a neighborhood over a landmark, leaving one day with nothing booked. That’s the part a spreadsheet can’t do for you.