Phrase origin

[stroma]

What is the origin of the phrase 'plain sailing'?

[sddsddean]

Another one from the Navy. Ships carried two basic sets of sails, storm sail (heavy canvas and very hard to handle on a yard arm 100 or so feet above deck) and plain sail (much lighter, made from light canvas or calico for smaller sails). Plain sail was much easier to handle, so the sailors looked forward to easier work with 'plain sailing'.

[Quizmonster]

'Plain sailing, in the 'easy/straightforward' sense in which we use it nowadays, was originally spelt 'plane' - ie flat - sailing and meant navigating a course that involved no difficulties or obstructions. It has been used in this way for at least three centuries.