Sailing the Red Sea 

Shagging a girl that has her period.

Having sex with a girl that's menstruating.

Sailing the Red Sea by Dutchgit December 16, 2003

Sailing the Seas of Cheese 

The phrase "Sailing the Seas of Cheese" means that the speaker is experiencing great personal change. The Seas of Cheese is an album made by "Primus" in 1991. The album's title is referenced throughout the album, and referenced in many albums after this ones release.

David: "Hey Lauren! We miss you back home! How's Chicago treating you?"
Lauren: "David. David I'm not good. I'm Sailing the Seas of Cheese right now..."
David: "What? Oh Lauren what happened? Are you-"
Lauren: "I had to drop out of school Dave. Mark left me a-and, I have to dance to pay the bills and..."

Sailing the Seas of Cheese by Sauce Mane November 16, 2018

Sailing on the Pumpkin Tide 

Refers to becoming drunk while alone in order to enhance one's creative process. Probably originated in the webcomic Problem Slueth.

Person 1: Can you come over tonight?
Person 2: No, I've had some ideas rolling around so tonight is going to be for sailing on the pumpkin tide.

Sailing on the Pumpkin Tide by Analog_man June 18, 2011

Sailing mishap 

Accident involving a sailing yacht.

"You look the same age to me."
"I'M FIVE YEARS OLDER AND IN COLLEGE!!!"
SAILING MISHAP!!!!

Sailing mishap by Snake January 16, 2005

Sailing the Red Sea 

Shagging a girl that has her period.

" If that means I have to sail the Red Sea that so be it but I need a shag now !

Sailing the Red Sea by Dutchgit December 16, 2003

sailing for cock 

sailing for cock

v. the act of sailing the high seas for a delicious cock

This act is especially common at frat halloween parties where many females are dressed as slutty sailors. These skanks are clearly not sailing a boat, ergo they are sailing for a nice cock to ride.

Emily was sailing for cock last night, but luckily captain Buckalas was there to give it to her.

sailing for cock by Fast Ed December 10, 2009

sailing around the cape 

When a man or woman performs oral sex on a female partner by starting at the clitoris then slowly working the tongue completely around to end up on the anus.

My boyfriend munched my rug so passionately last night and even licked me from my clitoris all the way to my asshole. I just LOVE it when he goes sailing around the cape!

sailing around the cape by Haley Mills February 13, 2009