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]
c. 1200, beatunge "action of inflicting blows," verbal noun from beat (v.). The meaning "pulsation" is recorded from c. 1600. The nautical sense of "sailing against the wind" is by 1883.
1540s, "give a cant to an edge," from cant (n.2). From 1741 as "put in an oblique position;" in sailing, "move obliquely," 1784. Related: Canted; canting.
word-forming element meaning "oblique," before vowels lox-, from Greek loxos "bent to the side, slanting, oblique," figuratively "ambiguous," a word of uncertain origin. As in loxodromics "art of oblique sailing" (1670s).
"large, seagoing Chinese sailing ship," 1610s, from Portuguese junco, from Malay (Austronesian) jong "ship, large boat" (13c.), probably from Javanese djong. In English 16c. as giunche, iunco.
1934, in Ezra Pound: "periplum, not as land looks on a map / but as sea board seen by men sailing" [Canto LIX], or as Hugh Kenner described it, "The image of successive discoveries breaking upon the consciousness of the voyager ..., the voyage of discovery among facts, ... contrasted with the conventions and artificialities of the bird's-eye view afforded by the map," from accusative of Latin periplus, in classical use "a written list of the ports and coastal landmarks, in order, with approximate distances between, that a ship's captain could use to navigate a shore."
From Greek periplous, contracted from periploos, literally "a sailing round," from peri (prep.) "around, about, beyond" (from PIE root *per- (1) "forward") + ploos "a sailing, voyage, navigation," from plein "to navigate" (from PIE root *pleu- "to flow").
"make headway by sailing, head in a certain course," late 14c., literally "to push the stem through," from stem (n.) in the "ship post" sense (here the post at the prow of the ship). Related: Stemmed; stemming.