Sailing Jokes

Here's a collection of some of the Krikkit crew's favourite sailing jokes. (Well, okay, technically that's not quite true because most of the crew's favourite jokes can't be repeated in public. But these are still pretty good, even if they are a bit tame.)


A new crewmember was talking to the bowman about the crew positions and dynamics. Bowman says “Well, there’s the front of the boat where all the interesting stuff happens, the middle of the boat where people sit around and have a good time, and the back of the boat where all the decisions are made. Otherwise known as Adventureland, Playland and Fantasyland.”


After a race, five crewmembers are together talking about plans for the big weekend regatta. One of them, who’s only ever on the boat for weeknight evening racing, asks the other four, “How’d you get your spouses to give you passes to go racing every weekend and every Wednesday night for the beer can races?”

The tactician says, “You just need to treat your spouse nicely. I made a deal with my wife that before heading out for a weekend regatta, I make her breakfast in bed.”

The jib trimmer chips in, “Ha, that sounds like a lot of work! My husband wanted a BMW, so I bought one for him and he lets me sail all I want. Done!”

The main trimmer responds, “A BMW? That’s one hell of an expense! My wife just wanted a diamond earring and necklace set she’d seen at Tiffany’s. It was only a couple thousand dollars, so I bought it for her and that was plenty enough. Now she lets me sail all I want.”

The bowman looks at them and shakes his head, saying, “Man, you lot have it all wrong. I wake my wife up with an elbow in the ribs at 5:30 a.m. and ask, ‘Race course or intercourse?’ and she says, ‘Get the hell out of here.’”


A new boat owner has his boated hauled out for painting and minor repairs, and the yard says it'll take two weeks. Three weeks later the boat's still not ready.

Concerned, the owner asks what the delay is. “Delay?" says the yard manager. "No, we’re right on schedule."

“But you said it would take two weeks," says the owner, "and it’s been three weeks already."

“Ah!," says the yard manager, looking the owner square in the eye. "That was two nautical weeks. Like nautical miles, they’re a little longer."


Q: How many boaters does it take to change a lightbulb?

A: None, because the right size bulb isn’t on board, the local marine-supply store doesn’t carry that brand, and the mail-order house has them on back-order.


Brian and Jim were lifelong friends and shared many experiences.

Following a blustery Fall Series race, Brian returned home and his wife asked how it went. Brian told her "We got a great start at the boat end and caught a right-hand shift that put us about 10 boatlengths up shortly after the gun. When the wind went back left we tacked on the header, went around the windward mark in first place and hit every shift downwind. The kite came down like prom queen's dress and the second lap was much like the first. We just kept stretching it out on the fleet. During the last beat, while grinding the headsail in, Jim dropped dead of a heart attack. We tried CPR, but it was no use, he was gone."

Brian's wife was understandably upset at the news of a dear friend's untimely demise. Her heart poured out to her husband and she had difficulty finding words to comfort him. Finally, she hugged him and whispered, "I'm so sorry - it must have been awful".

Brian replied "I'll say. After that it was - tack the boat, drag Jim to the high side - tack the boat, drag Jim to the high side".


Philosophical question of the day: If the skipper says something in the middle of the ocean where there's no one around to hear it, is he still wrong?


Bob had a terrible reputation as skipper. One Friday evening after a regatta delivery trip he was motoring back and forth through the crowded anchorage, searching for a place to drop the hook before dark. Looking up to heaven he said, “Lord take pity on me. If you find me a good spot, I will donate to charity, give up the demon rum, treat women with respect, pay my taxes, and never again give my crew all of the blame and none of the glory!”

Miraculously, the boat with the best spot in the bay began pulling up anchor to leave. Skipper Bob looked up again and said, “Never mind, I found one myself.”


An old sea captain was sitting on a bench near the wharf when a young man walked up and sat down. The young man had spiked hair and each spike was a different color – green, red, orange, blue, and yellow.

The young man, noticing that the captain was staring at him, turned to him and said “What’s the matter old timer—never done anything wild in your life?”

The old captain snorted. “Sure. I got drunk once and married a parrot. I was just wondering if you were my son!”


A sailor who finally reached port after being out at sea for two months stops at a brothel. He walks straight up to the Madam, drops down $500 and says, “I want your ugliest woman and a grilled cheese sandwich!” The Madam is astonished. “But sir, for that kind of money you could have one of my prettiest ladies and a three-course meal.” The sailor replies, “Listen darlin’, I’m not horny – I’m just homesick.”


A cruise ship passes by a remote island, and all the passengers see a bearded man 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.”