30 Hilariously Funny Sailing Quotes: Sailing and Boating Quotes to Make You Laugh


Let’s be honest, if you’re a sailor and don’t have a great sense of humor something is wrong with you. Sailing inevitably involves boat work, and if you’ve found yourself folded into a pretzel in a small compartment and drop a small boat part that falls into the bilge you really should start to laugh at some point, because if you don’t you’ll probably start to cry.

Whether it’s boat work, no wind, dropping something overboard, or how much money sailboats require, laughing is a required coping mechanism.

These are some of the funniest quotes about sailing and boats we love.

There are two types of sailors, those that have run aground, and those that lie about it. -Author Unknown

If anything’s going to happen, it’s going to happen out there. -Captain Ron

Now and then we had a hope that if we lived and were good, God would permit us to be pirates. -Mark Twain

Why is the rum gone? –Captain Jack Sparrow

A diesel loves her oil same as a sailor loves rum. -Captain Ron

Work like a captain and play like a pirate. –Author Unknown

The sea finds out everything you did wrong. –Francis Stokes

Any damn fool can navigate the world sober. It takes a really good sailor to do it drunk. –Sir Francis Chichester

A sailor is an artist whose medium is the wind. Live passionately, even if it kills you because something is going to kill you anyway. –Webb Chiles

Only two sailors, in my experience, never ran aground. One never left port, and the other was an atrocious liar. –Don Bamford

The pessimist complains about the wind; the optimist expects it to change; the realist adjusts the sails. –William Arthur Ward

There is nothing, absolutely nothing, half so much worth doing as simply messing about in boats. –Kenneth Grahame

Sailors, with their built-in sense of order, service and discipline, should really be running the world. –Nicholas Monsarrat

Give a man a fish and feed him for a day. Give him a fishing lesson and he’ll sit in a boat drinking beer every weekend. –Alex Blackwell

Sailing – The fine art of slowly going nowhere at great expense while being cold, wet and miserable. –Irv Heller

I shared this insight with some other boat owners, and they all agreed that, definitely, putting your boat into the water is asking for trouble. Most of them have had their boats sitting in their driveways long enough to be registered historical landmarks. –Dave Barry

I’m pretty sure my birthstone is a sea shell. –Author Unknown

There is nothing as relaxing as being out on the open sea, listening to the waves and the wind and the sails and voices downstairs yelling “HOW DO YOU FLUSH THESE TOILETS? –Dave Barry

It takes a minimum of six people, working in close harmony, to successfully flush a nautical toilet. That’s why those old ships carried such large crews. –Dave Barry

Life is like the ocean, it goes up and down. –Vanessa Paradis

You have to be careful on the deck, because of the “hatches,” which are holes placed around a sailboat at random to increase the insurance rates. –Dave Barry

Fortunately the boat we rented had a motor in it You will definitely want this feature on your sailboat too, because if you put up the sails, the boat tips way over, and you could spill your beer. –Dave Barry

The Ancient Mariner would not have taken so well if it had been called The Old Sailor. –Samuel Butler

He’s a boating enthusiast, although that phrase seems too weak to describe the level of his interest, kind of like describing someone as a heroin fancier. –Dave Barry

I swear like a sailor, assuming the sailor in question died in 1800 and was really square. –Alexandra Petri

Sailboats are the slowest form of transportation on Earth with the possible exception of airline flights that go through O’Hare. –Dave Barry

A bad day sailing is 100 times better than a good day at work. –Author Unknown

How to Sail a Sailboat by Dave Barry

  • 1.    Figure out where you want to go
  • 2.    Whichever way it is, do NOT aim the sailboat in that direction
  • 3.    Aim the sailboat in some other direction
  • 4.    Trust me, this is the way sailboaters do it
  • 5.    They are heavy drinkers

I had to choose between her and the boat, she said. Any sailor will know it is a lot more difficult to get a new boat than a new wife, so I bought her a one-way ticket back to Norway. –Peter Tangvald

A rough day at sea is still better than any day in the office. –Anonymous

If there are any other good sailing quotes you think should be on this list please email me at sywildrose@gmail.com so I can add them to the list.

Be Wild.

These are some of the funniest quotes about sailing and boats we love.

These are some of the funniest quotes about sailing and boats we love.