Traditional square topsail schooner Shenandoah
, sailing in Nantucket Sound.
The first detailed definition of a schooner, describing the vessel as two-masted vessel with fore and aft gaff-rigged sails appeared in 1769 in William Falconer's, Universal Dictionary of the Marine.
According to the language scholar Walter William Skeat, the term schooner comes from scoon, while the sch spelling comes from the later adoption of the Dutch spelling ("schoener"). Another study suggests that a Dutch expression praising ornate schooner yachts in the 17th century, "een schoone Schip", may have led to the term "schooner" being used by English speakers to describe the early versions of the schooner rig as it evolved in England and America. The Dutch word "schoon(e)" means nice, clean, good looking.
A popular legend holds that the first schooner was built by builder
Andrew Robinson and launched in Gloucester, Massachusetts where a spectator exclaimed "Oh how she scoons", scoon being similar to scone, a Scots word meaning to skip along the surface of the water. Robinson replied, "A schooner let her be." The launch is variously described as being in 1713 or 1745. Naval architects such as Howard Chapelle have dismissed this invention story as a "childish fable", but some language scholars feel that the legend may support a Gloucester origin of the word.
Other sources state the etymology as unknown and uncertain.