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?
Did you expect me to say anything other than YES?
by MajorSailor December 20, 2009
The fine art of getting really wet, really cold, going nowhere really fast, while spending large amounts of money
by jackts9999 May 4, 2009
A sport that includes leaping over centerboard housing every time you tack causing lots of bruises and cuts on your legs; especially in a 420 (by the way - it's a type of boat - nothing to do with pot dumbasses) and if you are lucky enough not to be cut or bruised on your legs you probably have a concussion from being too slow to duck during a tack or gybe.
by Sailor_Savvy August 27, 2007
The Greatest Sport in the world. Where you sail a boat via the sail catching wind. You can also race sailboats in something called a regatta this is equivelent to a swim meet on a boat, consisting of a number of races where the boat who did the best overall wins the regatta.
by Tom Russell August 18, 2005
To all you dumb fucks who think it is sexual, it is a piece of material extended on a mast to catch the wind and propel a sail boat. Or as a verb it means to go sailing.
"Do you sail?"
"Yeah, I went sailing last weekend and came back soaked and tired."
"That dude has a giant sail on his sailboat!"
"Yeah, I bet that boat does great in regattas!"
"Yeah, I went sailing last weekend and came back soaked and tired."
"That dude has a giant sail on his sailboat!"
"Yeah, I bet that boat does great in regattas!"
by Ija Renrut December 9, 2013
"sail" is a homosexual term that means "wander from gay bar to gay bar, not leaving until you've let someone 'drop anchor' in your butthole".
J. Dyer has been sailing between Hulas, Angles and The Man Hole all night but hasn't found any takers
by CaptainAloha July 13, 2018