There was a story on the BBC Worldnews telecast Monday night related to this topic. It seems that two British travelers opted to make their own flight arrangements for their dream trip to Sydney, Australia. However, apparently being neophytes at the intricacies of drop-down menus and three-letter airport codes they inadvertantly purchased two tickets to Sydney, Nova Scotia, Canada. According to the story they did not realize their error until their arrival in Canada.

I'm sure they must have been congratulating themselves on the remarkably low fare they managed to find for a flight to the other side of the world.

As far as the namesake for both cities, I'd venture to guess that the original Sydney is located somewhere in Scotland. Basing my guess on the observation that while traveling in Nova Scotia (New Scotland in Latin) virtually every locale's name had its origins in Scotland.

John in San Diego (marveling at the extremely low fare I found to Moscow...hmmm...that ID after the Moscow must be some Russian abbreviation...)