All of my initial psychedelic voyages were solo. Then for a few years most were in group settings (i.e. college), then I went back to mostly-solo and stuck with that ever since.
My first experience of altered consciousness of any sort (even before smoking cannabis) was eating an entire quarter-ounce of indoor-grown cubensis in my room by myself with my parents asleep upstairs. That's what happens when neither you nor the guy you got them from has any clue what you're doing, lol.
And it changed everything, which was just what I needed. It saved my life. Literally.
So eating a quarter of dry mushrooms alone in total darkness (and silence) might not be for everyone but it worked very, very well for me. I was lucky that where I lived at the time was pretty dark and quiet at night, with howling coyotes and occasional Border Patrol helicopters being the most common night time noises.
In my experience a lack of any external stimuli maximizes the chance that you will actually go on a "trip," and I find the presence of a sitter to be anchoring and I can't go nearly as deep with anyone else around, even if they're tripping too.
Follow your intuition.
I am contemplating following a system like the John Hopkins experiments, and wearing a shade, laying on my back and listening to music. However, every time I have had a journey it has been outside during the day. I live near a lot of woods, and I have been lucky enough not to get too lost or walk away. Too be completely honest I have been wanting to do a night time ritual under the moon, but I am very worried about freaking out in the dark. I do have a fear of the dark. Yet a moonlit ceremony seems to keep calling to me. I have always had a sitter, because I am worried about getting behind the wheel of a car or wondering off.
Big fan of moonless nights myself. I had the best trip experience ever starting up at the stars as the warm heavy wind whipped all around me, making the tree's dance across the skyline
Reading all these posts about solo tripping. I have come to realize the difference that it makes when you separate yourself from stimuli to achieve an actual trip. It happened to me one time by accident and It was an entirely different type of experience
Three of us came home after a night of drinking and scarfed down handfuls of shrooms. After a while I just wandered outside and was in love with nature. I was outside, by myself, In the dark, laying down starting up at the stars. The wind provided a sort of white noise cancelling out all other sounds. I remember at one point thinking about how our planet is going how ever many thousands of miles and hour through space. I could feel the sensation that the earth was moving, a sort of extra push of gravity throughout my entire body. Tears of joy from feeling so connected to the universe. And then abruptly It was interrupted. My friend came outside and called my name. It snapped me back into realizing I was a person again
With friends can be a hilarious memorable time, but I will never forget that solo experience