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There was a conversation I read a while ago that showed how a sailboat could travel a straight line over water from Halifax, Nova Scotia in Canada, travel southeast and end up on the west coast of British Columbia.
Basically sailing from the east coast of Canada to the west coast of Canada in a straight line.
The line was published by David Cooke in this YouTube video. It lies on a plane but is not quite a great circle (in practice, you'd be turning slightly) and good luck sailing over the Antarctic ice shelfs this decade.
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