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
"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
by Rik February 2, 2005
by Travis November 23, 2004
by rjthedudee November 13, 2018