The bigger the boat, the smoother the sailing.

A response to the phrase "it's not the size of the boat, it's the motion of the ocean".

Implies that "size matters".

Woman - "Wow dude, that's a really below average penis."

Man - "It's not the size of the boat, it's the motion of the ocean!"

Woman - "Maybe. But the bigger the boat, the smoother the sailing."

by Dakron July 11, 2014

Torrey Pines Sailing Team

A bunch of retards banded together to sail boats, who fight over retarded things, led by retards, funded by retards, and supported by rich retards

Did you hear about the torrey pines sailing team?
Yeah can’t remember the last time they stopped fighting and won a race

by Dipdip123 September 24, 2018

"Well, then. We sail without him!"

Line from the movie "Wedding Crashers" uttered by the legendary Christopher Walken. Can be used whenever someone fails to show at a pre-determined time or is inexplicably missing. A more polite way of saying, "Well, if he doesn't wanna go, then fuck him!"

"Where's Sak?"
"He's still sick."
"Well, then. We sail without him!"

by Tom Bosch March 24, 2006

hoist up the john b's sail

to say that you are going to go home

I'll see you guys later, I am going to hoist up the john b's sail.

by bgomez August 20, 2006

My ship hath/has sailed

A phrase many shippers use to say that their ship has been confirmed. Oftentimes, a headcannon.

Andrew: My ship hath/has sailed!
Mark: What ship?
Andrew: You know, my headcannon.

by EWild December 18, 2019

A good pirate also sails on the red sea

If your girl's on her period, who cares, just fuck her.

Hey man, I want to fuck my girlfriend tonight but it's her period and it'll be a bloody mess.
- cmon dude, a good pirate also sails on the red sea.

by reggiemt April 20, 2017

Urban Sail

When a breeze kicks up and your umbrella becomes either uncontrollable, inverts itself in your hands, or flies from your grip.

Synonyms: urban kite, umbrella sail, umbrella kite

"Umbrellas are a pain in the ass. Sure, they protect your head and shoulders from the rain, but the second the slightest breeze kicks up, you suddenly find yourself the unwitting mast for an urban sail that, best case scenario, inverts itself in your hands, and worst case scenario, flies from your grip, whips down the street and spears the Pope in the neck." - Tracy V.

Source: Cracked.com, Tracy V. (Invictus99)

by notfeelingcreative June 4, 2014