Reports in the early internet booking era of one or two who wanted to go by plane from London to Sydney, Australia, and ended up going to Sydney, Nova Scotia, in Canada. Newspaper accounts under a "how can you be so silly" headline.
However, it's an example of how transport companies could think a bit more. The travel website they used had just taken for destination selection an alphabetical city list from a USA website, and there were, blandly right next to each other in the list, Sydney NS and then Sydney NSW, for Nova Scotia and New South Wales respectively. No other qualification. It's no wonder more mistakes weren't made there. Travel on a Canadian airline a pointer? They were actively promoting their flight connections from London to Australia at the time, through Vancouver and Hawaii.