yard sailing 

A phrase used to describe the art of shopping at large numbers of yard sales, garage sales, and estate sales.

"I can't WAIT to go yard sailing this weekend!"

"Yard sailing is my favorite activity of late."

"There's nothing I would rather do than go yard sailing."

yard sailing by www.babysue.com May 9, 2006

sailing with the captain

To drink large quantities of Captain Morgan's Rum, usually with a group, and hopefully to the point of oblivion.

That girl I hooked up with was so fugly that I had to go sailing with the captain before I could bang her.

sailing with the captain by Robb December 24, 2003

Sky Sailing

Sky Sailing is Adam Young's OLD Pre-Owl City project. It consists of mainly laid-back and acoustic songs. It has recently been released to the public. Any Adam Young / Owl City fans should check this out!

Sky Sailing uses NO AUTO-TUNE! It doesn't sound like Owl City. It's much more beautiful.

Me: Oh, I love Adam Young's project, Sky Sailing. Its so relaxing.

Friend: Oh, I prefer his project, Owl City. The auto-tune makes him sound nice.

Friend 2: I think he sounds PERFECT either way!

Sky Sailing by Smile4Music June 21, 2011

College Sailing 

The only sport on campus where you can compete and travel with members of the opposite sex. Must be adept at hiking out (hooking your feet under straps while hanging your butt over the edge of the boat) in all weather conditions and leaning in (to the bar) after the regattas. Typically a good sport for engineers who like the physics of how boats work and business majors who enjoy the sport's social side. College sailors will learn fun new vocabulary words like croakie, burgee, halyard and roll tack. Many students join college sailing teams for the cool swag.

I joined college sailing so I can travel to regattas, meet preppy guys and party at the yacht club.

College Sailing by Sailing Ace September 6, 2013

Sailing 

sailing: (v.) to manhandle the wind as to propel a sailboat on the very edge of catastrophe. see also: insanity, beastlyness, and epic.

Dude, you wanna go sailing today? It's blowing 35 knots

Did you expect me to say anything other than YES?

Sailing by MajorSailor December 21, 2009

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