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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.
Sailing Rules. Comon Everyone's doing it
sailing by Tom Russell September 14, 2005

garage sailing 

The pasttime of attending garage sales in pursuit of other peoples junk that may or may not be cool.
I think we'll go garage sailing this weekend for Velvet Elvis'.
garage sailing by rzklkng August 25, 2003

Speedo Sailing

When a male and/or males receive oral sex from an anonymous person's father, then proceed to buy plane tickets to Finland.
"Dude I'm tired of school, need to get off, and would like to travel, lets go speedo sailing
Speedo Sailing by Overdose of Tums January 12, 2011
a kool sport, that is on da water
i am going sailing with my frends
Sailing by Rik February 2, 2005

Sailing to Tibet 

A phrase describing an idea that is poorly thought out. First used in the Mission district of San Francisco.
Adam is totally sailing to Tibet with his plan to quit his job and become a private investigator.

garage sailing 

The process of driving from garage sale to garage sale (or yard sale, etc) in suburban areas without any real specific goal in mind, or maybe some rough goal, such as "getting a bookshelf." It usually involves intensive haggling over prices.
We woke up early saturday morning to go garage sailing.
garage sailing by nuage August 26, 2003