For me it boils down to what the trip is for. If people have different objectives, it's a recipe for disaster. I like to enjoy the scenery by riding my bike. I have no interest in finding access to the internet. I don't want to hang around camp any longer than necessary. I like stopping for pancakes. I don't want to fish the rivers we pass. I have no interest in trying my luck at casinos or in bars. I don't want to score any weed or get drunk.
Group trips work only when there is mutual dependence and the trip couldn't continue for either party if one person bails. It's otherwise just too easy to go your separate ways when conflict arises.