General Patton
Bluelighter
I mostly trip at home, lounging around listening to music. I might play some guitar if I feel like it and towards the end get more interested in socialising with others or just watching some tv/film.
I also obsess over the number 4444.
I think we share some of the same thoughts, at least with regards to tripping habits and numerical obsessions

The trip was pretty much my way of facing my own obsessive psychology, I ended up meeting a special entity that helped me do this, it worked out well in the end. It got me to see my habits and my life in general as a kind of cosmic comedy that I can play out my role in, instead of just being swept up in it.
To awnser the question in the OP, it really doesn't matter what you do while tripping. As long as you stay in the moment and get the most out of your stay you can find the transcendence in almost anything... In nature, as well as from looking at buildings, hell I've even had some pretty incredible trips to the bathroom! Just relax, go with the flow, float downstream and you'll get where you need to go.