Plain Sailing Watch this on YouTube here - Nautical Video - YouTube Video Meaning: Plain Sailing means to be an untroubled task or easy. it is a nautical term that means the sailing is easy and uncomplicated. Origin: This phrase started out many years ago when the majority of people thought the earth was flat, and not round. The term was used a “Plane Sailing,” to represent the ocean being flat, so a route from one place to another did not take in the curvature of the planet, instead, it was a flat plane ocean. Now we spell it “Plain” in the sense of ordinary and uncomplicated. This way of writing shows that a task will be easy or uncomplicated. The first written record of this phrase uses the term plain as in ordinary and was in 1683 by Adam Martindale in A Collection of Letters for Improvement of Husbandry & Trade. It read: “A token for ship boys, plain-sailing made more plain and short than usually, in three particular methods.” Example: Today we still use plain sail...