Perfectly straightforward; an easy and unobstructed course. The term comes from navigation, where it means sailing in waters that are free of hazards, particularly rocks or other obstructions. Used since the nineteenth century, it may have come from the earlier navigational term
plane sailing, the art of determining a ship’s position without reference to the fact that the earth is round, and therefore sailing on a plane (flat surface), which works, but only for a short distance.
Plain sailing was transferred to other pursuits in the early nineteenth century. Shaw used it in his preface to
Androcles and the Lion (1916): “Without the proper clues the gospels are . . . incredible. . . . But with the clues they are fairly plain sailing.” A synonymous term is
smooth sailing, used figuratively since the first half of the 1800s. Edward Bulwer Lytton had it in
Night and Morning (1841), “‘Oh, then it’s all smooth sailing,’ replied the other.” See also
hard/tough sledding.