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.
by Robb December 24, 2003
mugGet the sailing with the captainmug.

Skin Sail

Yo, look at the skin sails on that old lady over there
by cheeseman 2010 July 20, 2016
mugGet the Skin Sailmug.

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!
by Smile4Music June 21, 2011
mugGet the Sky Sailingmug.

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.
by Sailing Ace September 6, 2013
mugGet the College Sailingmug.

sail boating

the act of pressing you nose against a flat chested woman and just blowing
Did you motorboat sarah's friend last night? Nope, just went sail boating, there where no boobs!
by Touge_Drifter September 19, 2012
mugGet the sail boatingmug.

Sail Out

Referring to Jhené Aiko's EP "Sail Out", the phrase means to "Be free, go with the wind, like a sailboat."
"It's really important to sail out when it comes to peace... inner peace especially. You can't help anyone else if you don't have it together yourself."
by Aikooo December 22, 2022
mugGet the Sail Outmug.

Share this definition