I lived in Halifax, Nova Scotia, Canada (eh?) for 23 years and we have similar stories. There is an island that is part of Nova Scotia called Cape Breton with a city named Sydney (so Sydney, Nova Scotia, Canada) with population of ~30K. Every few years we get a tourist that confuses that with Sydney, New South Wales, Australia. They generally realize something is wrong when they switch planes in Halifax from a Jet (B…
I was flying to Costa Rica from Montreal. Airline wanted money for checked luggage, but typically for long distance flights like this it's free. After enquiring, turns out I had bought the wrong flight to San Jose, California, instead of San Jose, Costa Rica. It's SJC vs SJO too, easy to confuse... Glad I figured that out before getting there!
https://en.m.wikipedia.org/wiki/Do_You_Know_the_Way_to_San_J...