sailing: (v.) to manhandle the wind as to propel a sailboat on the very edge of catastrophe. see also: insanity, beastlyness, and epic.
Dude, you wanna go sailing today? It's blowing 35 knots

Did you expect me to say anything other than YES?
by MajorSailor December 20, 2009
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The fine art of getting really wet, really cold, going nowhere really fast, while spending large amounts of money
Sailing owns, though
by jackts9999 May 03, 2009
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a kool sport, that is on da water
i am going sailing with my frends
by Rik February 02, 2005
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To drink Sailor Jerrys Rum
"Yo dude, wanna go sailing later?"
or
"Bruce is sailing this evening!"
by hanw June 18, 2008
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Entering into a sexual relationship with another person. The act of "sailing," of course, makes reference to the piloting of a ship, not unlike the sort of maneuvering or establishment of control inherent in the act of sexual intercourse.
"If you sailing her that's an L chief."
by john quan the first September 05, 2018
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