Sailing Jokes - 56 Hilarious Sailing Jokes

While sailing, I had trouble navigating the waters between Russia and Alaska.

I couldn't get my bearings straight.

A dear friend of mine fell overboard while sailing the other day

Sadly, he couldn't swim, so he quickly drowned.
At the funeral service, I gifted his family a life preserver.
It's what he would have wanted.

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A grammar nazi pirate is sailing his ship getting ready to attack an enemy ship...

when one of his men comes up to him and hollers:

*"The cannons be ready, Captain!"*

The Captain looks at him and says:

*"Arrrrrrrrrre"*

Olympic Results for Sailing are out:

The British have taken the Gold medal.

The French have taken the Silver medal.

The Somalians have taken the boats.

How do you know if you'll like sailing?

Put on a thick yellow raincoat, and stuff it with hundred dollar bills. Step into the shower, turn it on full blast and it's coldest temperature, and just start stuffing those bills down the drain. If you've managed to somehow enjoy yourself doing this, you might just be crazy enough to enjoy sailin...

So a three masted sailing ship is leaving port...

... just a day out of port the captain is standing on the deck when the lookout calls down "Sir! There's an enemy ship on the horizon!"

The captain turns to his cabin boy and shouts "Bring me my red shirt!"

After the cabin boy brings him the red shirt and he puts it on, the two ships...

A British trawler is sailing off the coast of Germany when suddenly the ship starts taking in water.

The ship is sinking fast and the captain immediately gets on the radio to contact the German coast guard.

"Help!" he exclaims, "We're sinking! We're sinking!"

A hesistant voice comes from the radio. "Um...v-vot are you sinking about?"

Long ago, when sailing ships rules the waves

Long ago, when sailing ships ruled the waves, a captain and his crew were in danger of being boarded by a pirate ship. As the crew became frantic, the captain bellowed to his First Mate, "Bring me my red shirt!". The First Mate quickly retrieved the captain's red shirt, which the captain put on and ...

A ship sailing past a remote island spots a man who’s been stranded there for several years.

The captain goes ashore to rescue the man and notices three huts…

“What’s the first hut for?” he asks.

“That’s my house,” says the castaway.

“What’s the second hut for?”

“That’s my church.”

“And the third hut?”

“Oh, that?” sniffs the castaway. “That’s ...

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(NSFW) Two whales are swimming in the ocean and discover a little sailing boat...

one whale asks the other:

"Do you want to have some fun? Let's swim under the boat and blow air to make the boat capsize!"

He agrees. So they dive under the boat, blow air and the boat flips.

"This was fun. What do you think about eating the sailors? It would be a shame to let t...

Did you hear about the dog who owned a leaky three-masted sailing ship?

His barque was worse than his bite.

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A married couple are sailing with a young tour guide.

There's a sudden storm and the boat gets destroyed. Luckily, all three of them survive and manage to swim towards a small island.

Once they've caught their breath, the tour guide speaks. "Let's take turns keeping watch for any ships that come by for help. I'll climb up that palm tree and keep...

A man has the opportunity to win a million dollars if he can cross lake Superior in a 16 foot sailboat...

The people sponsoring the challenge give the man two choices of what he can bring on the boat to assist him. He can either bring a large box of novels or two criminals. However, the people running the competition get to choose what the books are and who the criminals are.

The man realizes the...

The Somalian Olympics team has just apologised

The Somalian Olympics Team has just apologised to the Olympic Committee after realising that sailing and shooting were 2 separate events!!

Captain, are u sure we're sailing to Italy?

-Of course.
-But the compass is upside down.
-Off course.

Somalia swept the Olympic sailing podium

They earned gold, silver, and bronze despite starting the event with one entry

A school teacher in Hyderabad was once asked, "Can you make a sentence without using 'E'?"

"I doubt I can. It’s a major part of many many words. Omitting it is as hard as making muffins without flour. It’s as hard as spitting without saliva, napping without a pillow, driving a train without tracks, sailing to Russia without a boat, washing your hands without soap. And, anyway, what would ...

A cruise ship is sailing in the Caribbean..

The cruise ship passes by a remote island, and all the passengers see a bearded man with an eyepatch running around and waving his arms wildly.

“Captain,” one passenger asks, “who is that man over there?”

“I have no idea,” the captain says, “but he goes nuts every year when we pass him...

My wife didn't finish her Morse code lessons before going sailing.

She seems to alright though she keeps sending me messages to send her an SMS but I haven't got a reply yet.

One fine day, brave Captain Smith and his crew of sailors were sailing the ocean blue.

Suddenly, on the horizon, there loomed a ship with a skull and crossbones raised on the mast.

The crew was frantic, seeking refuge and asking the captain what to do.

Brave Captain Smith looked at the approaching ship for a moment and said: “Bring me my red shirt”.

The call was t...

It's fine to be enthusiastic about sailing...

Just don't go overboard

An ocean liner is sailing in the North Atlantic and hits an iceberg.

As the ship is sinking, one crewman runs to the ship’s captain and tells him to open the root beer caskets in the ship’s hold.

The captain is confused but has no other options, so he orders all of the ship’s root beer caskets cut open. The root beer floods the hold and the ship slowly stops s...

A ship is sailing through the sea...

passing by a small island and watches a man screaming and shouting.

A passenger asks the captain:

- Who is he?

- We don't know, he gets crazy every year we pass here.

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Sailing aboard the new cruise liner SS Penis is by invitation only.

It's an exclusive member ship.

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Will I Live to see 80?

Will I Live to see 80?

Here's something to think about.

I recently picked a new primary care doctor. After two visits and exhaustive Lab tests, He
said I was doing fairly well for my age.

A little concerned about that comment, I couldn't resist asking him, 'Do you think ...

Olympic Sailing results are in!

Denmark have taken gold

Finland have taken silver

Somalia have taken a middle aged couple who were on a worldwide cruise

I was sailing my boat when a massive hand rose out of the water and then slowly disappeared.

I thought, "Thats the biggest wave I’ve ever seen."

Olympic sailing competition just finished. France got the gold, South Africa got the silver, and ...

Somalia got the boat.

A ship was sailing in the middle of the ocean....

A storm was developing in the distance. As the storm raged, the captain realised the ship was sinking fast.

He called out loud, "Anyone here knows how to pray?"

A man proudly raised his hand and came forward, "Aye Captain, I know how to pray."

The Captain replied, "Great, you ke...

Why do pirates avoid sailing in shallow water?

With only one eye, they have terrible depth perception.

Have you ever had the privilege of sailing across the North Atlantic Sea?

Neither has the Titanic.

Some pirates are sailing off the coast of Madagascar

The captain points to the shore and says to his first mate:

"Do you see those crazy looking lemur things?"

To which the first mate replied:

"Aye aye, I eye aye-aye"

A US Ship was sailing through dense fog when it sees another light....

US Ship: Please divert your course 0.5 degrees to the south to avoid a collision.

CND reply: Recommend you divert your course 15 degrees to the South to avoid a collision.

US Ship: This is the Captain of a US Navy Ship. I say again, divert your course.

CND reply: No. I say again...

Two ships crash into each other on a densely foggy day on the ocean.

The two captains (a man and a woman) wind up in the same hospital and they fall in love. They give up their sailing careers to raise a family.

When the wife was almost ready to give birth, they decided it would be really sweet if their child chose a career that would be helpful in preventing...

Thought I’d try translating a joke. Two foreigners are sailing to America for work.

Upon getting off the boat at the dock, one notices a hotdog stand. Sure, it sounds weird to them but they decide to try it.

As one unwraps the foil, he blushes and asks, “Which part of the dog did you get?”

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A man joins the crew of a sailing ship.

After a few days he gets restless and asks "What does one do about sex around here?"

The others direct him to a large barrel with a hole in it. At first he does not like the idea much but, when he tries it, he finds it surprisingly enjoyable. He has another go the next day, and again the d...

How long would you be sailing if you were to sail 220 yards at a speed of one nautical mile an hour?

Knot furlong.

Our sailing trip in Maine was going great...

until we were capsized by Augusta wind.

What did the Canadian say to the other Canadian when they saw a guy in a giant pink bathtub sailing around in circles in the middle of Lake Ontario?

"What's that, a boat?"

Pirates are sailing when...

... in the distance 2 ships are spotted, all the pirates are called to man their stations and prepare for battle. The captain tells his trusty shipmate to get his red vest. The ship is damaged but the battle against the two ships is won. After the battle the captain's mate says to him, "why dd you a...

Why did the nun go to confession after sailing?

The boat was full of seamen.

An admiral is sailing a ship...

and ahead of him, spots an incoming light. He radios the light, commanding, "Turn 10 degrees South to avoid a collision course." The radio squawked, "No, you are to turn 10 degrees South." This exchange happens about 3 or 4 more times until finally, the admiral yells into the radio, saying, "Do you ...

Last night, I dreamt that I was sailing in a sea of soda.

I wish I could go back to that Fanta sea.

3 sailors crash their boat while sailing close to the shore of an unexplored island.

After moving inland, they are captured by members of an indigenous tribe. The tribesmen take the sailors to their chief. The chief, in very broken English, speaks to them,

"You trespass here, now I have test for you. Go deep into forest. Pick for me 3 fruits, and return to me. The test begins...

An English navy ship is sailing off the coast of Germany...

When the ship runs into a giant boulder underwater and starts sinking.

The captain quickly gets on the radio and says "Mayday mayday. This is the English navy we are sinking. I repeat we are sinking." With no response from the German navy base.

After numerous attempts they finally he...

A pirate ship is sailing in the ocean when an enemy ship approaches...

"Captain, an enemy ship approaches!" A crew member shouted from the crow's nest.

The captain turned to his first mate and said, "Bring me my red shirt." The first mate, somewhat confused, ran to the captain's quarters and brought the captain his red shirt. They battled the enemy ship and won....

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It has been mentioned that when cruises start sailing again, the buffets will all be staffed with servers instead of just serving yourself.

The saddest job will be the person who has to push the buttons on the pop dispenser. Why? Because it is "soda pressing".

I will see myself out.

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The billionaire and the mermaid whisperer

A billionaire is sailing his yacht past a lighthouse, and he sees the elderly lighthouse keeper out on the rocks at the base of the lighthouse, getting a blowjob from a mermaid - the top half was a stunning, curvy redhead, and the bottom half was a tiger shark. As he watches, the pair finish the act...

An American is sailing in German waters when his boat starts to take in lots of water.

Realizing he won't be able to make it to shore, he calls the German Coast Guard.

"I'm sinking, I am sinking!"

The operator replies "Vhat are you sinking about?"

A group of men are out sailing when they decide to see what the chef is cooking for dinner.

They walk in and, being that he doesn’t have a rolling pin, see him flattening biscuits with his armpit.

“That’s disgusting!” One guy says to the other.

“Yeah, well you should see how he makes donuts!”

Why don’t the Jedi have a navy?

Because sailing is a path to the dockside.

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A college professor gets offered a chance to teach sex education which is not what he usually teaches.

He’s a little embarrassed to tell his wife what he’s teaching so he tells her he’s teaching a class on sailing. A few months go by and his wife runs into a friend’s daughter who says, “I’m really enjoying your husbands class!”

The professor’s wife says, “Oh?…I’m surprised, he’s only done it o...

What do you call a group of guys, sailing the sea, singing about looting and stealing?

21 pirates.

Ponce de Leon began his journey to find the Fountain Of Youth

"But captain," a crewmate said. "Are you sure the fountain even exists?"

"Hmm," Ponce pondered. "Maybe you're right. Maybe this trip would be a waste of time."

"So, are we going back?" The crewmate asked.

"No, we're not going home empty handed," Ponce replied.

"So, wha...

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Sandy was the youngest of five brothers born in a poor family in 19th century Scotland.

When he came of age, Sandy decided to cross the seas to America to seek his fortune. Scots are thrifty and hardworking, so Sandy prospered in his new home. After twenty years, he decided the time had come, so he booked passage on a sailing ship to cross the sea again and return to his native land fo...

The Captain's red shirt

Bored of living in poverty in the late 1700's, Finn decides he wants a slice of the pie in the high stakes world of pirates. He knows pirates dock down in the bay by his village, so once he spots them, he manages to sneak aboard one of the ships. He eventually gets discovered, and rather than throw ...

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