The one year it happened with full cover was via the Ltd Co working as contractor to a larger events company who had an EU base, the Ltd Co had general PLI for that.
Being outside the EU with no Authorised Representative there makes it almost impossible to get direct cover via the Ltd Co only but the AR point could be resolved if someone wanted to go back down that road. Being outside established event norms and not being a staffed event also created questions for insurers. “What are you actually doing / insuring?” “Just riding our bikes self-supported from a group start…?” “Is that an event?” .. and hence me thinking that somewhere in all this is a format and guidelines for an event that is not really an event. More of a happening, more easily managed and covered. But maybe not since it can look and sound like a kind of event.