The Ship is Sailing 

When you want 2 people to date you ship them, when they do end up dating, that’s when “the ship is sailing”

Hey! Did you hear that jack and Leslie are finally together?

No way! The ship is sailing!

The Ship is Sailing by MysteryLife13 January 9, 2021

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

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

Pussy Sailing 

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.

Pussy Sailing by Druidbegone December 18, 2009

garage sailing 

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.

garage sailing by arcan August 25, 2003

pussy sailing 

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!

pussy sailing by pussysailer April 4, 2011