sailing wait 

How many times a loaded ferry will travel to its destination and back before it it your turn to get on.

It's looks like it's about 3 sailing waits down at the ferry terminal.

sailing wait by SpiderRider3 June 5, 2010

Sailing the internet 

To illegally download content, internet piracy.

So whatcha doing tonight?
I'm sailing the internet looking for movies

Sailing the internet by fluffypenis August 13, 2017

Sailing to Tibet 

A phrase describing an idea that is poorly thought out. First used in the Mission district of San Francisco.

Adam is totally sailing to Tibet with his plan to quit his job and become a private investigator.

Sailing to Tibet by Krankiboy June 7, 2007

Sailing Away

A song by the band Styx that is considered a classic. It is so happy and cheery-sounding that it makes people want to punch something.

Song: "I'm Sailing Awayyyyy....."

Person: "AHHH GOD!!!!" *goes nuts and punches a wall*

Sailing Away by Fruuze March 4, 2009

Sailing Ship 

A ship that has a large amount of people shipping it. Most ships have only a few people who like the ship, however, if the ship gains popularity, it may start "sailing"

"wow I never would have expected for (insert ship name here) to become a sailing ship" -a random person who is commenting on a sailing ship

Sailing Ship by Friccingfricfac August 5, 2019

Sailing with the Captain

A Song by the Celtic rock band Dust Rhinos about Drinking lots of Captain Morgan Rum

I was sailing with the Captain, he'll show me the sights, I wish tomorrow morning would be as good as tonight

Sailing with the Captain by btm321 December 1, 2010

Sailing the sea of brown

The awkward run that you make when attempting to hold your sphincter shut while running to the bathroom when suffering from a case of explosive diarrhea.

Oh wow, looks like Bob is sailing the sea of brown!

Sailing the sea of brown by Steve Chuttney April 7, 2011