Ask HN: You're planning a vacation to somewhere, what's your process?

I'm planning a trip in November. I'm curious if anyone has some novel way to find interesting places and places at their trip's destination. I personally am the type of planner that plans a few major things and leaves room for what my friends and I call "side quests". We're never too formal which sometimes bites us in the butt but overall gives us a lot of flexibility.

I'm wondering if there might be some tool or framework others use to plan trips.