Meaning of plain sailing

plain' sail'ing

Pronunciation: [key]
  1. sailing on waters that are free of hazards or obstructions. Cf.
  2. 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.