Set Sail Mateys! Swashbuckling Words Ahead

Avast, mateys!

Arrr! Welcome aboard landlubbers! Pirates and sailors alike use a complex set of vernacular to operate their ships and navigate the open seas. Curiously, dozens of these nautical terms have crept into mainstream language. Whether you’re heading out on a luxury cruise or simply landlocked like the rest of us, brush up on this list of seafaring words.


We’ll set sail with a homophone; two words with the same sound but different meanings/spellings. On the boat, a gaff is “a spar rising aft from a mast to support the head of a quadrilateral fore-and-aft sail.” If you commit a gaffe on land, that would be an embarrassing “social faux pas or blunder.”

High And Dry

If you leave someone high and dry on land, you’re basically leaving them with no way out; they’re stuck. In nautical parlance, this term basically refers to a beached boat. It’s run aground and not going anywhere anytime soon. Think “Minnow” from Gilligan’s Island.


Are you feeling groggy? We’d usually associate that term with someone that’s not fully awake. The term is derived from the sea. Well, kinda sorta. Here’s the story, as reported by The Phrase Finder. “Groggy” is derived from the word grog, which is an alcoholic drink. Arrrrr. Feel free to start talkin’ like a pirate at this point, matey.

So why is it called “grog?” It seems that a fellow named Admiral Edward Vernon was an officer in the British Royal Navy way back when. He fancied wearing grogram jackets to keep warm. He also liked to water down his crew’s rum ration, so it wouldn’t be quite as potent. The crew didn’t much care for that, so they called him “Old Grog” and that’s what they also named his weak beverage. The crew knew what they were talking about—at one point their daily drink ration was a gallon of beer.

Loose Cannon

If you’re a loose cannon, you’re rather reckless and unpredictable. Back in the day, though, the term literally referred to loose cannons on the deck of sailing ships. These massive guns had rollers on the bottom and were anchored by ropes, and if they came loose in the course of battle, well, there you go.


If you admire the cut of one’s jib, you’re basically saying you admire their appearance, their demeanor, and their overall presence. It feels very Brooks Brothers, very masculine. You just wouldn’t use this to describe a female in present-day.

Three Sheets To The Wind

The contemporary meaning is that you’re drunk. This kind of relates to grog. The term is also derived from the current nautical word sheet. To sailors, a sheet is a “rope or chain for extending the clews of a square sail along a yard, a rope for trimming a fore-and-aft sail, or a rope or chain for extending the lee clew of a course.”

Hard And Fast

As in a hard and fast rule. There’s no getting around it. This term originally applied to a vessel that has come out of water, either by running aground or being put in dry dock. This term is similiar to high and dry.

Shake A Leg

You can thank the Royal Navy for this term. It was used to wake drunk or sleeping sailors. Another meaning refers to the fact that women were allowed on board Royal Navy vessels in the 19th century, and they were allowed to stay in bed after the sailors got up. So, they were told to shake a leg to distinguish themselves from the rest of their, er, bunk mates.

Clean Bill Of Health

This is what you want after you go to the doctor for a checkup, and that’s how we use it in everyday use. On the water, it refers to “a certificate signed by a port authority attesting that no contagious disease existed in the port of departure and none of crew were infected with a disease at the time of sailing,” according to the website Dear Surprise.


You hear this term on the cable news channels. Of course, filibusters are used by politicians to delay passage of a bill. But the term originates far from the floors of the House or Senate. It seems that olde-tyme buccaneers were sometimes known as filibusters in England.


Now, stop snickering, there’s a real meaning here. In everyday usage, it means you’re tired, as in “I’m pooped.” Where in the nautical world does this come from? Glad you asked, sailor. In a nautical sense, a poop deck is defined as “a superstructure at the stern of a vessel.” If a ship were unlucky enough to be overtaken by a massive, breaking sea which drenched her from astern, she was said to have been “pooped.”

Slush Fund

We know slush fund as “a sum of money used for illicit or corrupt political purposes, as for buying influence.” We also note that slush is actually refuse fat from a ship. After returning to port, sailors would sell off any leftover fat on board. The slush fund proceeds were then used to buy items for the ship’s crew.

Pipe Down

Did your parents ever yell “pipe down!” during your sleepovers with friends? That’s how we know it today. The original nautical usage describes when a senior deckhand would play the last signal on his pipe at the end of the day. Time for lights out, men.

Son Of A Gun!

The term can be used a variety of ways, depending on inflection. If you’re referring to a person and say son of a gun in a rather irritated tone, we call them a “a rogue; a rascal; a scoundrel.” You can say it with amazement in your voice, meaning you’re totally surprised, too. “The Cubs won the Series? Son of a gun!” Going back in the day, 17th and 18th century sailors had a different meaning. Women would sometimes give birth on ships. If the father couldn’t be determined, the child was known as “a son of a gun.”

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