Etymology
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sailing (n.)

Old English seglinge, "act of one who or that which sails," verbal noun from the source of sail (v.). Gradually coming also to mean "the art or rules of directing a ship." Figurative use of smooth sailing for "easy progress" is from 1840.

Yes; I must press on this marriage; Georgina has not wit enough to manage him—at least till he's her husband, and then all women find it smooth sailing. [Bulwer Lytton, "Money: A Comedy in Five Acts," 1840]

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Definitions of sailing

sailing (n.)
the work of a sailor;
Synonyms: seafaring / navigation
sailing (n.)
riding in a sailboat;
sailing (n.)
the departure of a vessel from a port;
sailing (n.)
the activity of flying a glider;
Synonyms: glide / gliding / sailplaning / soaring
From wordnet.princeton.edu