/ Dictionary / Index P plain sailing: Meaning and Definition of Find definitions for: plain' sail'ing Pronunciation: [key] sailing on waters that are free of hazards or obstructions. Cf. an easy and unobstructed way, course, or plan: As an heir to a large fortune, he looked forward to financial plain sailing. Random House Unabridged Dictionary, Copyright © 1997, by Random House, Inc., on Infoplease. plain sail plain-saw Related Content Daily Word Quiz: secular Analogy of the Day: Today’s Analogy Spelling Bee: Today’s Spelling Bee Frequently Misspelled Words Frequently Mispronounced Words Easily Confused Words Writing & Language