Sailing Phrases

10 Phrases You Never Knew Came From Sailing

When you stop to think about it… sailing is pretty amazing. From a historical perspective, through its role in travel, trade and war, it was the absolute hinge of western civilization for hundreds of years. Through that time, sailors’ slang and terminology became rooted in the English lexicon and still exists profoundly to this day.

Here’s a list of 10 everyday phrases that you may not have realized were born in the days when sailing made the world go round… wait… is that a nautical phrase?

  1. “A clean bill of health”
    According to this phrase derives from the days when the crew of ocean going ships might be a little less than hygienic, so they needed to present a certificate, carried by a ship, attesting to the presence or absence of infectious diseases among the ship’s crew and at the port from which it has come.

  1. “Feeling Blue”
    How often do you hear people talking about feeling blue or have the blues? An entire genre of music comes from this phrase. Who knew that came from the world of sailing? explains the popular phrase comes from a custom that was practiced when a ship lost its captain during a voyage. The ship would fly blue flags and have a blue band painted along her hull when she returned to port.
  1. “Pipe down”
    Parents have been screaming “pipe down” to their kids forever, but where does that actually come from? Apparently, Pipe Down was the last signal from the Bosun’s pipe each day, which meant lights-out, quiet down, time to go to bed.
  1. “Over a barrel”
    We all know when someone has you “over a barrel” things aren’t going well. This saying is used all the time these days to indicate being severely compromised, but it began in the most literal way. Sailor crew would sometimes be punished for their misgivings and that involved being tied over a cannon barrel and whipped. It’s no wonder that one stuck around. Yikes.
  1. “Toe the line”
    Perhaps you’ve been at work and your boss has scowled at you and said, “toe the line, or you’re gone”. If this has happened to you, we are sorry, that sounds like a horrible work environment. But, if you were wondering about the origins of his demand, it’s an old naval expression that refers to a ship’s crew who would be called to gather and form a line with their toes all touching a given seam (or line) of the deck planking.
  1. “By and Large”
    Folks say this one all the time to refer to the big picture. “By and large, ASA is the most awesome organization in existence”… something like that. This term got started on a sailboat with the word “by” meaning into the wind and “large” meaning off the wind. So sailors would say: “By and large this ship handles quite nicely.”
  1. “Loose cannon”
    Everyone has known a few people who are loose cannons – unpredictable and dangerous on some level. Not surprisingly the term comes from when a ship’s cannon would come loose from it’s lashing. The big dangerous thing would be sliding all over the place making for some uncomfortable time on deck trying to get that bad boy back in its spot.
  1. “A square meal”
    People often talk about getting three “square meals” a day…what the hell is a square meal? It’s actually quite simple – the wooden plates back in the days of tall ships were square.
  1. “Hand over fist”
    These days this phrase usually refers to making a bunch of money, although it can refer to anything happening fast and in abundance. It comes from a more literal origin – sailors would be tugging at lines as fast as they could, hand over fist, to trim sheets and raise sails.
  1. “Son of a gun”
    It’s amazing that this phrase has lasted so long. Back in the day, as you might imagine, sailors were often less than virtuous and every once in a while a “lady friend” of a crewman might give birth to a child on the ship. A good spot for this sort of thing was between the guns on the gun deck. Now let’s say this little rascal isn’t claimed by any of the aforementioned sleazy sailors, this little grommet would sometimes be called a “son of a gun”.
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Nice list! Here are 10 more old sailing phrases that I thought would be interesting enough to add (with their current meanings in parentheses): 1. Shake a Leg (meaning to hurry up) originally meant “to dance.” “Every man able to shake a leg bought a ticket to the dance.” 2. Turning a Blind Eye (to intentionally ignore something) came from the Battle of Copenhagen in 1801, when Admiral Lord Nelson deliberately held his telescope to his blind eye, in order not to see the flag signal from the commander to stop attacking the enemy. [Nelson won the battle 😉 ]… Read more »

I thought “Feeling Blue” came from the Blue Peter (code flag Papa).
This is the signal that the ship is ready to sail and all sailors and passengers need to report aboard immediately. From a sailors perspective, his “peter” was not going to get any company for several months, if not years, and is probably tied the the phrase “blue balls” as well.


funny. but blue balls?


Love this! I use a bunch of nautical sayings daily, and now I realize I use a lot more!

N. Matthew

Another good one is “posh”. Originally it was P.O.S.H., an acronym, on seafaring travelers’ tickets from England to and from India, it indicated Port – Out, Starboard-Home accommodations, which meant your cabin was on the shaded, and more comfortable, side of the vessel for both passages, hence, posh.

Neill Parker

Correct about the meaning of the POSH acronym. Except that it was the North Atlantic being crossed to North America, an east-west voyage though a cold place, even in warmer months. So the desirable cabins were the on sunny side each way. The trip to India involved a lot of north and southbound navigating, where neither side was towards or away from the sun.


I read in B. Tuchman’s book about the American Revolution that “tow the line” referred to the Brit navy’s practice of literally linking warships together during combat or maneuvers, not to cut loose and be spontaneous rogues during battle. Stay in formation at all costs.
“Toe the line” seems more like what runners would do at a track meet?


Toe the line is correct. Ships in line of battle were never, ever linked together. Each ship in line of battle needed to be able to maneuver to stay in line and tying the ship’s together would have prevented this. Tuchman is wrong on this account.

Andrew Reinbach

You forgot “the devil to pay”. The devil is the space between the top deck and the hull. It had to be “payed”–filled in with tar–to keep the barky dry. This was a tedious job on the best day, because there’s usually a ledge directly over the devil. So the devil to pa means something you want to avoid at all costs, but can’t.

The same applies to “between the devil and the deep blue sea”, because sometimes, the only way to get at the devil was to be suspended over the side, stuck between two bad alternatives.

I quibble with many of these imperfect definitions however “the devil to pay” is the most egregious mistake. The lowest seam in a carvel planked wooden ship is the Devil seam….between the keel and the garboard strake….this is the most difficult to “pay” because of the upwards angle and the amount of movment between these two parts. The full quote is “The Tide is rising and the devil to pay” this refers to a careened or dried out ship on the hard with the tide rising but the lowest seam not yet sealed up. Note pay means to caulk with… Read more »
John R Otten

Freeze The Balls Of A Brass Monkey – A Brass Monkey was the dish that cannon balls were stacked upon onboard to stop them rolling around the deck. In normal temperatures they held the cannon balls without any problem but when it got really freezing the Brass Monkies (dishes) contracted to an extent that they could not contain the balls and they would topple off. Hence the phrase

Davis Pillsbury

I think you are correct. Add water. Along a ten mile stretch of US 70 east of Glenwood Springs, Colorado, called “Glenwood Canyon”, boulders the size of VWs roll down the canyon walls crushing people, cars and the elevated highway. Some feel it is the coincidence of rain and temperature. Warm enough to rain, then cold enough to expand the water: when it freezes, the boulders lift just enough…

Taylor Davies

Also the ‘bitter end’ as in “I’ll fight this to the bitter end” comes from sailing.

It refers to the very last point where an anchor is attached to the ship, usually via a large pin, which can be removed using a sledge hammer should the anchor slip or fail.

Ray neville

The bitter end is the unfinished end of a piece of rope or line. It will fray and worry off unless fininshed so there is no way to effectively belay it.


Sorry to say so but that’s not right, the bitter end is the following end of a rope, used particularly when splicing, ‘make an eye at the second mark and feed through it the bitter end’, subsequently the end of anything can be referred to as the bitter end. 🙂

mark thierman

i was told the term “two sheets to the wind” meaning drunk or unstable comes from when you let go of both jib sheets (on accident usually) and the jib would flap around in the wind without form or stiftness.

Laughing gull

It was actually two sheets on the lower square sail called a “course”. The lower sail has four sheets – 2 on each Lower corner. When you let two go the sail kind of pulls. It fills and sags and then fills again. It looks just like a drunk guy walking down the road.

Michelle LeBarron

Three sheets to the wind comes from the windmill keeper. When 3 sheet were to the wind it made the windmill off kilter. So when the windmill keeper got drunk he would throw the mill off kilter affecting the power etc… the people in town would recognize it and say The windmill keeper is 3 sheets to the wind 😊

Rich Simrin

My dad always said “3 sheets in the wind” to describe his teen age sons who had too much to drink

Ed Foote
I don’t think brass contracts enough in the cold to change sizes so much that it loses the cannon balls. There are two” devils” on a wooden ship, one down at the joint between keel and planking, and the other where the decking meets the sides. Two terms associated with them are “Between the devil and the deep blue sea” which referred to being on the very edge of the boat, between the upper devil and the sea, i.e. safety was behind you and danger in front. “The devil to pay” comes from the need to “pay”, or caulk, the… Read more »
Clay Commons

“The devil to pay” comes from the christian bible. Sailors added “and no pitch hot”, meaning a hard piece of work, like paying that last seam, and no materials handy to do it.

Val Mccourt

The Devil is actually the seam where the deck meets the ships side
Another term is between the devil and the deep blue sea this meant that the man was outside of the bulwark and therefor was between the devil and the sea.

Dave Olney

“Skylarking”… Playing around like birds in the Top Rigging.
Topriggers were wiry, nimble, arrogant and cocky – an agile breed apart from the average crew – and ancestral archetypes of “Trapeze” artists & “Tightrope” walkers.
“Rievers” were those specially deft and dauntless ones who had to go aloft to lash sails to the spars, do seeing repairs or set lines through the blocks (and shieves), sometimes “hanging by their teeth.”


Know/Learn the ropes


“Strike while the iron is hot” – the timely use of superheated cannon balls to inflict maximum damage to the opposing ship in a naval battle.


Love these. This made me think of a post I wrote about some frequently mispronounced nautical terms.


Surprised no one mentioned “Beat a dead horse.”

Bob McKenna

“Go by the board” to abandon or reject in 17th century nautical term was “something overboard” as a mast or boom etc.

Davis Pillsbury

Ahoy there, fellow salts!

The use of salt is interesting. Sailing ships were packed with salt in places never to be seen again, such as “the knees” Salt preserved the wood to avoid dry rot.

“The horse latitudes” Let’s see what you have to say about that term.

Visible evidence of a “Cape Horner” was the ear ring. Which side?


The side of the pass


Touch and go, refers to the practice of just touching one shore before tacking towards the other when attempting to make way upstream within the confines of a river or estuary.


My grandfather was a turn of the century sailor of pre-motorized ships, and spent 20 of his first years aboard. He had great tales to tell, and I remember one especially as it shocked me as a child. He said the “bitter end” was the frayed end of the line on the bucket used to wipe ones bottom after using said bucket as a toilet.

Tony Innocent

From a historical perspective, through its role in travel, trade and war, it was the absolute hinge of western civilization for hundreds of years. Through that time, sailors’ slang and terminology became rooted in the English lexicon and still exists profoundly to this day.