The act of going from one garage sale to the next, to the next, to the next, and so on and so forth. Taking a day or a weekend or a few hours to desperately search for other people’s junk.
Me and Fred are going garage sailing this weekend you should join us, we’re too broke to go to the store....
by Descriptiongiver101 August 16, 2019
"Dude, did you see Jenny in her new bikini at the pool?"
"Yeah man, I saw her while I was practicing my backstrokes. She had me Sail Boating."
"Yeah man, I saw her while I was practicing my backstrokes. She had me Sail Boating."
by Sarpa May 26, 2016
by TeamCook January 21, 2019
When booking an outing with a seaside shop offering “sails and cervix” package-tours, one should make sure to ask if their standard price includes having your gorgeous guide spread her legs for you, or if said delightful “extra” actually COSTS “extra”!
by QuacksO October 08, 2023
When a man takes his erect penis and in a smooth "sailing" motion runs it along the butthole of a prone person.
The other day Kenny tied a little sail to his dick and went dirt sailing before throwing a piece of eight on her back!
by Habberstamp July 10, 2022
by Neverendbro December 15, 2010
by Young and Fun July 05, 2018