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.
39๐ 17๐
The act of "sailing" many female genitalia's in the width of one cruise. To have sexual relations with many woman in one sitting
Andrew: Dude, Broken told me the other day that he was going pussy sailing for some ass and I laughed hysterically.
Sandy: Broken can't go pussy sailing, hes missing the sail.
Andrew: that is not all he is missing.
53๐ 25๐
The act of "hopping" from one garage sail to another, often with the assistance of a newspaper listing.
Dave and Theresa got up brigh and early every saturday and went garage sailing.
15๐ 5๐
A manuever pulled when a person easily fails something without very much effort or thought put into it.
That honors class was so hard that I just sail failed right though it.
COD team full of private match instaswappers and nac mod losers
โHey, Can i join XOโ
โNah XO doesnโt recruit instaswappers, but I heard Sail Mob is recruitingโ
when lads go out in their car's looking for some pussy
"Got my car fixed earlier mate, fancy going pussy sailing tonight?"
"Yeah! Pick me up, and we'll go!
8๐ 2๐
A song by the band Styx that is considered a classic. It is so happy and cheery-sounding that it makes people want to punch something.
Song: "I'm Sailing Awayyyyy....."
Person: "AHHH GOD!!!!" *goes nuts and punches a wall*
5๐ 1๐