sail·ing (s??l?ng)n.1. The skill required to operate and navigate a vessel; navigation.2. The sport or pastime of operating or riding in a sailboat.3. Departure or time of departure from a port.American Heritage® Dictionary of the English Language, Fifth Edition. Copyright © 2016 by Houghton Mifflin Harcourt Publishing Company. Published by Houghton Mifflin Harcourt Publishing Company. All rights reserved.sailing (?se?l??) n1. (Nautical Terms) the practice, art, or technique of sailing a vessel2. (Nautical Terms) a method of navigating a vessel: rhumb-line sailing. 3. (Nautical Terms) an instance of a vessel’s leaving a port: scheduled for a midnight sailing. Collins English Dictionary ? Complete and Unabridged, 12th Edition 2014 © HarperCollins Publishers 1991, 1994, 1998, 2000, 2003, 2006, 2007, 2009, 2011, 2014sail?ing (?se? l??) n. 1. the activity of one that sails. 2. any of various methods for determining courses and distances by means of charts or with reference to longitudes and latitudes, great circles, etc. Random House Kernerman Webster’s College Dictionary, © 2010 K Dictionaries Ltd. Copyright 2005, 1997, 1991 by Random House, Inc. All rights reserved.sailingaloof – Comes from sailing, in which ships keep clear of coastal rocks by holding the vessel “luff”?”to the windward”; so, to hold “a-luff” means to “keep clear.”jibe – Meaning “be compatible, consistent,” it may come from the earlier jibe, “to shift a sail from side to side while sailing in the wind.”plain sailing – Probably comes from plane sailing, a way of determining a ship’s position based on its moving on a plane (flat surface).aback – Originated in sailing, as a ship was taken aback when a strong gust of wind suddenly blew the sails back against the mast, causing the ship to stop momentarily.Farlex Trivia Dictionary. © 2012 Farlex, Inc. All rights reserved.