Smooth Sailor 

A drink most commonly consumed by those who attend Eckerd College. A bitch drink. For those lacking the ability to handle their liquor.

Bro 1: Brah, I can make you a gnarly Smooth Sailor.

Bro 2: Dude, man up and take a shot.

Smooth Sailor by 123456789ABCDDEFG December 8, 2010

Sailor's wank 

The practice of numbing one's action hand, generally through circulation restriction or ice application, for the purpose of pseudo-auto-erotic masturbation.

I.e., it feels like someone else is doing it. Popular extensions include shaving and manicuring the hand to give a visual as well as sensory illusion.

So called due to the increasingly eccentric and imaginative masturbation aids that long periods at sea causes.

Seaman Staines: Ahoy! Why is there no ice in the freezer?
Master Bates: Because I just used it all to numb my hand and rub out a cheeky Sailor's wank all over your insoles.

and

Captain Jack Sparrow: Ahar, me matey. Where's me rubber bands for me hair?
Roger the Cabin Boy: Sup Jack. I took your hair bands for an extravagant Sailor's wank on the poop deck. I can offer you this delicious, creamy white conditioner in return?

Sailor's wank by Bertie Ahern December 9, 2008

sailboat emoji 

A deeper way to express love or affection. Sailboat is regarded a higher form of love than that expressed in the word "love".

I ⛵️ (sailboat emoji) you

sailboat emoji by Douglas Sailboat Emoji December 16, 2014

Sailgating 

When a large group of sailboats gather in the bay. Until they all run out of beer. Tailgating for sailboats.

They're all sailgating in The Gulf of Mexico.

Sailgating by TheRiverviewGirls June 6, 2010

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

Sailrocket 

Triple rum and coke served in a pint glass. A drink commonly favoured among speed sailors.

Can I have a Sailrocket, go easy on the coke.

Sailrocket by rummy December 4, 2012