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
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"nice-guys don't go for anal"
Chantal: I thought gentlemen never sail to windward.
Rodriguez: I'm no gentleman, baby.
by Carl Figleaf August 15, 2022
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What a horny dude would hope dat da hot female skippers of a schooner-tours company would offer.
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 8, 2023
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"Set your sail" is a way of say something excites someone.
Ex. Good looking men set my sail.
Ex. What ever sets your sail!
by Young and Fun July 5, 2018
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A woman that gives a blowjob to everyone in the room all in a line.
Bitch, you totaly cum sailed that party the other night!
by Yermum69n June 26, 2017
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To spend long periods of time on one's front porch. Usually involves music, conversation and some form of inebriates. May also involve food, especially food produced from a grill.
I'm just planning to sail the porch tonight, you can come hang, too.
by tehamahreha February 28, 2009
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Used when referring to a golf cart that has been taken off of (specifically) private property and driven down public roads illegally.
1. I saw Buddy sailing the fucking cart down the street like a champion who gave zero fucks.

2. Bill asked “how will we be getting there?” And Michael answered “fucking sailing the cart boiii !!!”
by harry pot May 15, 2018
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