It all depends on what kind of experience you're looking for, if you're just looking to party or have a good time, go out with friends. Personally I almost always trip alone, it allows me to really lose myself in my thoughts, get some good introspetive thinking done.
I used to trip by myself all the time; it's just the way that I started out doing things. Eventually, however, tripping caused me to be more open, and now I like to do shit while tripping. I usually find that candyflipping at a good concert is the best time of my life, but I used to think taking mad shrooms and chilling in my room by myself was the best. It's all in your personal preference, i.e, what you want to get from the trip.
i allways trip on my own but i allways trip very lightly. just some mild visuals... and i allways do fly agarics....