The farthest I've been is from Ashdod (a city in Israel, a very tiny middle-eastern country) to New York via plane (7 hours long... Though I slept through most of it because it was the night time in Israel, but it was night in NY when we got to NY... Stupid 11/7 hour difference (I don't really know. It's a 9 hour difference in Calgary from Israel)). Then probably from Calgary, Alberta to Victoria, British Columbia via car to Vancouver, then boat to Victoria.
I think the most interesting place I've been to was Drumheller, Alberta. Or Head Smashed In Buffalo Jump... :/