Honestly the most important and insightful trip I ever had was the very first time I tripped on anything which was LSD with a close friend of mine. We had spoken about doing it for a long time but could never seem to get hold of any (before the says of the DNM, at least as I was aware) and then, one day while walking in a local park we found this little velvet pouch. We picked it up and looked inside and there they were, four little tabs of LSD. We went home and took them later that night (maybe reckless but we were young and knew no better) and to say it opened my mind! I think I had always felt these feelings on connection to each and everyone, that we are all involved in the same struggles and joys, at essence we are all one and the same, but this trip exaggerated them beyond anything I could have expect.
We sat and shared what we were experiencing, the beauty and the patterns, the joys in music we never knew we could find (despite loving these bands our entire lives), sat in the garden and stared at the clear night sky and felt that amazing oneness with the universe and all that is in it. Pure love and joy and happiness, everything felt like it made sense. We were coming down and were both wondering how we ever go back to the way we were and since then, neither of us have. It really changed me on a fundamental level.
It will always be the most special of my trips even if not the most awe inspiring or mind blowing, I never lost who I was for example. It just showed me another way.
One other time I was tripping in a park with a different friend around 200ug each. It was the most glorious English summers day in a beautiful park full of little hidden spots and wildlife, once again we had this affirmation of the beauty in the world. Then as we were coming down, still suitably gone but not peaking any longer, we set off to walk back to his house. It had turned to night now and out of the comfort of the park (where we had spent around ten hours) and the chill on the night time and back in the urban city, everything seemed chaotic. Bright neon lights and cars whizzing around, drunk people spilling onto the streets. It was quite the jarring change. The we were walking home and this car pulled up and came to a screeching stop in front of us and these two people high on crack jumped out and demanded money and lighters from us, we were still tripping but we didn't react, it got a bit physical and we had to defend ourselves and run out of there. Still tripping quite a lot.
That was quite a nice reminder the world isn't all rainbows and unicorns.
I've had those heavy trips on shrooms and LSD, once a breakthrough on DMT, where you lose yourself and the ego dissolves and they were more profound in a 'religious' sense but the two above are for some reason, just special and stay with me on a more regular basis. Probably because they were easier to integrate the trips into everyday life than those 'showing you the universe' type trips. I never quite know how to use those in waking life.