Plain sailing

//ˌpleɪn ˈseɪlɪŋ// noun

Definitions

Noun
  1. 1
    The navigation of waters free from hazards or unfavourable winds. uncountable
  2. 2
    easy unobstructed progress wordnet
  3. 3
    Obsolete spelling of plane sailing (“a technique for navigation using the assumption that the journey occurs over a plane or flat surface rather than the actual curved surface of the Earth, which is sufficiently accurate over short distances”). alt-of, obsolete, uncountable

    "[…] I hired a Tonquineſe for about a Dollar to be my guide. This, tho but a ſmall matter, vvas a great deal out of my Pocket, vvho had not above 2 Dollars in all, vvhich I had gotten on board, by teaching ſome of our young Seamen Plain Sailing."

  4. 4
    Something that is easy, simple, or straightforward; something that offers no difficulties or trouble. figuratively, uncountable

    "[H]e ſhould give himſelf fair play, by trying his hand vvith the rudiments, vvhich vvould no ſooner be run over, than the reſt vvould become plain ſailing: […]"

Etymology

From plain (adjective) + sailing. Sense 2 (“something that is easy, simple, or straightforward”) is attested slightly later than plain-sailing (adjective), and so could have been derived from it.

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