[JimtheCoder]

I take the opposite approach to what you are doing...

I figure out something that I want to see/eat/experience, and then travel to the required destination.

If I am choosing a destination first, I am probably traveling there for the destination itself, and I don't really plan ahead or care about what is there...I just go and figure it out.

You mentioned flexibility...I think this is key. For me, itineraries or the "need" to have a schedule or do something causes stress, which is what I am trying to get away from when going on vacation.