> especially with the presence of which I’ll call “expectations of planning” in my immediate circle

Yeah, when traveling with others who do like/need to plan I'll go with their plans and flow unless it gets too boring. When traveling with my wife I'll even stick around even if I'm bored.

> Some people want the best possible experience

I mean, I do too! :) Just different methods of getting there.

> can’t be confident they aren’t missing out unless they have done the research

Man, just daily life must be tough if they're feeling FOMO from such low stakes situations, I couldn't handle that myself :/