Usually means: Smooth, easy progress without obstacles.
Definitions Related words Mentions
We found 19 dictionaries that define the word plain sailing:

General (16 matching dictionaries)
  1. plain sailing: Merriam-Webster.com
  2. plain sailing: Oxford Learner's Dictionaries
  3. plain sailing: Collins English Dictionary
  4. plain sailing: Vocabulary.com
  5. plain-sailing: Wordnik
  6. plain sailing: Wiktionary
  7. plain sailing: The Wordsmyth English Dictionary-Thesaurus
  8. plain sailing: Infoplease Dictionary
  9. plain sailing: Dictionary.com
  10. Plain Sailing (song): Wikipedia, the Free Encyclopedia
  11. plain sailing: Rhymezone
  12. plain sailing: Free Dictionary
  13. plain sailing: Mnemonic Dictionary
  14. plain sailing: Dictionary/thesaurus

Computing (1 matching dictionary)
  1. plain sailing: Encyclopedia

Tech (2 matching dictionaries)
  1. SeaTalk Dictionary of English Nautical Language (No longer online)
  2. Plain Sailing: Latitude Mexico

(Note: See plain_sailings as well.)

Definitions from Wiktionary (plain sailing)

noun:  (nautical)
noun:  The navigation of waters free from hazards or unfavourable winds.
noun:  (figurative) Something that is easy, simple, or straightforward; something that offers no difficulties or trouble.
noun:  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”). [(nautical) 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.]

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