The world of sailing has its own lively language — and honestly, some of these funny sailing phrases are pretty hilarious.

Whether you’re a seasoned sailor or just someone who loves dry land, reading up on these funny sailor sayings is very entertaining, to say the least.

You also might be surprised to learn how many of these sailing expressions have seamlessly drifted into our everyday conversations, carrying a ton of nautical heritage with them.

Some of this jargon is strictly for those brave enough to face the ocean’s waves, offering a fun glimpse into the lively and sometimes quirky language used on sailboats. These cheeky phrases capture the essence of a sailor’s life, reflecting both the challenges and joys of navigating the open seas.

If you’re interested in getting a handle on these sailing phrases, it’s worth spending some time learning the different parts of a sailboat — especially if you’re dreaming of your own sea adventure.

Mastering this lingo will not only make you sound like an old salt but also help you make light of the unpredictable tides of life.

What Are The Essential Funny Sailing Phrases To Know?

1. Batten Down the Hatches

Used to prepare for a storm or any difficult upcoming situation.

2. Aye Aye Captain 

A respectful acknowledgment of an order from a superior.

3. Fair Winds and Following Seas 

A way to wish someone luck on their journey.

4. Sheet Happens 

A humorous phrase for when things go awry on a sailing trip.

5. Ship-shape and Bristol Fashion 

This means something is well-organized or in excellent condition.

6. All Hands on Deck 

An order for everyone to help during a crisis.

7. Shiver Me Timbers 

An exclamation of surprise or excitement.

8. Walk the Plank 

A metaphor for facing an uncontrollable situation.

9. Keel Over

Describes a boat capsizing, or someone falling over.

10. Even Keel

Refers to a calm, stable state of mind or balance.

11. Taken Aback

To be astonished by an unwelcome occurrence.

12. Three Sheets to the Wind

A term used to describe someone who drank too much. Perhaps they got into the captain’s rum!

13. Between the Devil and the Deep Blue Sea

Describes a difficult situation with no good options.

14. Let the Cat Out of the Bag

To expose a hidden truth or secret.

15. Scuttlebutt

Gossip or rumors.

16. Anchors Aweigh

Denotes the beginning of a journey.

17. A Bone in Her Teeth

Describes a boat moving fast.

18. Tide Over

Refers to getting through a difficult period.

19. Sailing Close to the Wind

On the verge of doing something illegal or improper.

20. Cast Off

To release a mooring line or anchor so a vessel can set sail.

21. Dead Reckoning

A method of navigation based on estimated speed and direction of travel and using the points of a sail.

22. Helm’s Alee

A command used when tacking.

23. Square-rigged and Squared Away

A ship that has things in order.

24. A Shot Across the Bow

A warning or threat.

25. Crow’s Nest

A lookout point high on a mast.

26. Jibe Ho

A command spoken when jibing.

27. Lower the Boom

To put a stop to, chastise, or rebuke. In other words, to criticize someone when they did something personal to you.

28. Headwinds

Resistance or opposition to a plan.

29. Sea Legs

The ability to maintain balance or adjust to a new situation.

30. Run Aground; or High and Dry

A boat hits the sea floor and stops. Or a person stuck in an unfavorable situation.

31. Dead in the Water

A situation with zero chance of success.

32. Fathom

A nautical unit of measurement for depth or understanding (comprehension).

33. Gunwale

The upper edge of the side of a boat.

34. In Irons

When a sailing vessel is trapped and unable to move.

35. Kedge

A smaller anchor that is used to move the ship slowly in the desired direction.

36. The Cut of One’s Jib

The way one looks or conducts themselves.

37. Cup of Joe

A cup of coffee.

38. Groundswell

Describes a widespread surge of public opinion.

39. It’s an Ill Wind That Blows No Good

A phrase meaning that bad for one can be good for another.

40. Know the Ropes

To be well versed and familiar with something.

41. Bail Out

To remove water from a boat, or to abandon a difficult situation.

42. Loose Canon

Refers to someone who is unpredictable or uncontrollable.

43. Rudderless

Describes a person or situation lacking direction or control.

44. Man Overboard

An urgent call indicating someone has fallen off the vessel. Also used metaphorically for unexpected crises.

45. Trim The Sails

To adjust the sails for optimal performance. Often used to mean adjusting plans to improve results.

46. Chart A Course

To plan a route or direction, used metaphorically for setting a plan.

47. High Seas

Refers to international waters, often used to describe a risky or lawless situation.

48. Set Sail

To begin a journey or venture.

49. Broadside

Refers to the side of a ship. Also used metaphorically to mean a strong verbal attack.

50. Overhaul

To inspect and repair. Also used in a broader sense to mean making comprehensive changes or improvements.

Wrapping Up

As you can see, a lot of these funny sailing phrases are used in everyday language.

It just goes to show how engrained sailing culture is in American culture. 

This list of funny Nautical terms and phrases are what sailors would use on an everyday basis — think of them as old-timey nautical slang. 

If you think you’re ready to put your new vocab to use, book a sailing lesson here in Newport, RI, and master the art of sailing!

Fair winds, sailor!