
Rock the boat.
Add a touch of maritime wit to their home or cabin with our sailing joke fan pillows. Cozy, humorous, and full of nautical charm, they’re perfect for any sailing enthusiast’s space.
Rock the boat.
"I like my vodka like I like my ships - on the rocks!"
Captain looks out of a porthole and notices that the ship is sinking.
"Ticket and passport, please."
Lighthouse powered by batteries.
'I haven't been able to go to sleep in this new bowl.'
Early design for the Two-Man Kayak.
'I told you we should have unionized.'
Fisherman selling sardines in oil, haddock in oil, cod in oil etc..
"Let’s draw him closer to New Bedford — we’ll get cell service there and Instagram the heck out of this!"
'What do you mean the men are unhappy! What on earth gives you that idea?'
'It's great to get away from the rat race!'
'I think we should wake the Captain!'
Oceanographer
"You're goin' up the river, Sammy."
Angry pirate looking at angry parrot (wearing diaper) on his shoulder.
"Say, does anyone here know how to tie a sailor's knot?"
'I just got back form a class reunion!'
The skipper never wears a hat that fits. He's always been afraid of cap-sizing!
'It's bad news for the cabin boy.'
Overweight Passenger on a Boat
Captain Bligh, we refuse to swab the deck with paper towels! Near Great Movies: "Mutiny Over the Bounty."
Whale Pattern Balding
'After paying for the boat, it's insurance, the docking and gas, I couldn't afford a trailer.'
'I just think it might be a bit too jolly for the captain's taste.'
'I think it's A pep rally to promote school spirit.'
"Serious drinkers recommend hanging on to the maraschino."
"Rats, we can't bow ride this one: it's a hovercraft..."
"Stop repeating everything I say birdbrain!"
"Hi! I'm Greg Holbrook, born in L.A., now live in Stamford with my wife and three kids, went to school at Exeter, graduated Yale '38, did a two-year hitch in the Navy, now write copy for McCann-Erickson, my hobbies are tennis and sailing. Who are you and what do you do?"
'I guess the drinks are watered down!'
"Seriously, Mittens, let's let this one go."
"Gosh and I thought it was a barbershop."
A Jack Tar
Pants on the mast
Explore our full collection of sailor-inspired mugs with witty slogans and nautical humor—perfect for sailing joke fans who love a good laugh with their coffee.
Browse our charming sailing-themed prints to showcase witty and nautical artwork that celebrates a love of sailing and good humor.
Discover our range of humorous sailing t-shirts—ideal for those who enjoy sharing a laugh about their passion for the water and boats.