Etymology
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leeward (adj.)
"situated away from the wind, on the side opposite the weather side of a ship, pertaining to the quarter toward which the wind blows," 1660s, from lee + -ward. Also as an adverb. Similar formation in Dutch lijwaarts, German leewärts, Swedish lävart. The Leeward Islands are so called in reference to prevailing northeasterly trade winds.
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sag (n.)

"a bending or drooping," 1580s, in nautical use, "movement to leeward," from sag (v.). From 1727 in American English in reference to landforms having a sunken look. By 1861 in reference to droop from slackness in wires, cables, etc.

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leeway (n.)
also lee-way, 1660s, "sideways drift of a ship in her course caused by wind, deviation from true course by drifting to leeward," from lee + way (n.). Applied to loss of progress in general from 1827. Figurative meaning "extra space" is by 1835.
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clipper (n.)

late 14c., "sheep-shearer;" early 15c., "a barber;" c. 1300 as a surname; agent noun from Middle English clippen "shorten" (see clip (v.1)). In late 18c., the word principally meant "one who cuts off the edges of coins" for the precious metal.

The type of sailing ship with sharp lines and a great spread of canvas is so called from 1823 (in Cooper's "The Pilot"), probably from clip (v.1) in sense of "to move or run rapidly." Compare early 19c. clipper "person or animal who looks capable of fast running." Perhaps it was influenced by Middle Dutch klepper "swift horse," which is echoic (Clipper appears as the name of an English race horse in 1831). The nautical sense was perhaps originally simply "fast ship," regardless of type:

Well, you know, the Go-along-Gee was one o' your flash Irish cruisers — the first o' your fir-built frigates — and a clipper she was! Give her a foot o' the sheet, and she'd go like a witch — but somehow o'nother, she'd bag on a bowline to leeward. ["Naval Sketch-Book," by "An officer of rank," London, 1826]

The early association of the ships was with Baltimore, Maryland. Clipper-ship is attested from 1850.

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