• Q: I am a vessel without oars, sails, or a motor. What am I?
  A: A bottle floating at sea.
• Q: What always goes up but never comes down, especially on a ship?
  A: The mast.
• Q: What is a sailor’s favorite letter?
  A: Sea.
• Q: What has keys but can’t open locks, and keeps a ship’s secrets safe?
  A: A nautical chart.
• Q: I have cities, but no houses. I have mountains, but no trees. I have water, but no fish. What am I?
  A: A map of the ocean.
• Q: What travels around the world but stays in one spot on a ship?
  A: The globe.
• Q: What can fill a ship’s sails without wind?
  A: Enthusiasm.
• Q: What runs around the whole yard without moving?
  A: The rigging.
• Q: What is always in front of you but can’t be seen, even when on a sailing vessel?
  A: The future.
• Q: What has keys but can’t unlock anything, yet is essential for a sailor?
  A: Knots.
• Q: I’m the captain of a ship, but I’m not the person in charge. Who am I?
  A: The compass.
• Q: What can be cracked, made, told, and missed, all while sailing?
  A: Jokes on a cruise ship.
• Q: What is a ship’s favorite restaurant?
  A: The galley.
• Q: What runs around a ship but never moves?
  A: The deck.
• Q: I have a tail but no body, and I sail without wind. What am I?
  A: A ship’s pennant.
• Q: What has keys but can’t open locks, and sings a sailor’s song?
  A: A concertina.
• Q: What starts with a “P” and ends with an “E” and has more than 1000 letters?
  A: A postcard sent from a long voyage.
• Q: What has a head, a tail, is brown, and has no legs, yet helps guide a ship?
  A: An anchor.
• Q: What gets wetter as it dries, especially when hung from the mast?
  A: A ship’s flag.
• Q: What belongs to you, but other people use it more than you do on a crowded vessel?
  A: Your name.

• Q: What gets larger the more you take away from it, especially when stranded at sea?
  A: The ocean.
• Q: What is full of holes but still holds water, especially when patched up on a ship?
  A: A sail.
• Q: What can travel around the world while staying in a corner, especially on a nautical chart?
  A: A meridian line.
• Q: What is always on the lookout but never sees, especially on the bow of a ship?
  A: The figurehead.
• Q: What starts and ends with an “E” but only has one letter, especially when docked?
  A: An envelope used for sea mail.
• Q: What has a neck but no head, two arms but no hands, especially when used by sailors?
  A: A pair of rigging lines.
• Q: What is carried to sea but never leaves the ship, especially in a sailor’s heart?
  A: Memories of home.
• Q: What is as light as a feather, but even the world’s strongest sailor can’t hold it for long?
  A: A breath of wind.
• Q: What is always in front of you, but can never be reached, especially when lost at sea?
  A: The horizon.
• Q: What has eyes but can’t see, a deck but no cards, especially when it’s stormy?
  A: A ship in distress.
• Q: What has keys but can’t open doors, especially when guiding a ship through treacherous waters?
  A: A lighthouse.
• Q: What is always moving forward, never backward, especially when sailing with a favorable wind?
  A: Time on the open sea.
• Q: What starts with “E”, ends with “E”, and has a letter in it, especially when marking the stern?
  A: A ship’s nameplate.
• Q: What has a head, a tail, but no body, especially when used to mark shallow waters?
  A: A buoy.
• Q: What is full of holes but can still hold water, especially when fashioned into a makeshift bucket?
  A: A worn-out sailcloth.
• Q: What can you see, but never touch, especially when looking at the stars for navigation?
  A: Constellations.
• Q: What is tall when it’s young and short when it’s old, especially when swaying with the waves?
  A: A ship’s mast.
• Q: What is sharp as a tack but won’t poke you, especially when used to guide a ship’s course?
  A: A compass needle.
• Q: What has a head and a tail, but no body, especially when adorning a ship’s prow?
  A: A carved figurehead.
• Q: What can be seen during the day but not at night, especially when guiding a ship safely through channels?
  A: Daymarks.

Another Sailing riddles

• Q: What has keys but can’t open doors, especially when guiding a ship through fog?
  A: A foghorn.
• Q: What is always right behind you on a ship, especially when you’re not looking?
  A: The wake.
• Q: What has hands but never claps, especially when navigating with precision?
  A: The ship’s clock.
• Q: What is small, round, and can be seen from afar, especially when signaling distress?
  A: A flare.
• Q: What has a tail but no body, and helps the ship catch the wind?
  A: A sail’s telltale.
• Q: What is as tall as the sky, but fits in the palm of your hand?
  A: A ship’s model.
• Q: What gets heavier the more you add to it, especially when taking on provisions?
  A: The ship’s cargo hold.
• Q: What is always moving, yet never goes anywhere, especially when plotted on a chart?
  A: The ship’s course line.
• Q: What can you break without touching it, especially when it guides the ship’s path?
  A: The light of dawn.
• Q: What has a heart that never beats, especially when securing the ship to the dock?
  A: A mooring line.
• Q: What can be cracked, yet never broken, especially when it’s the code of the sea?
  A: A sailor’s signal flag.
• Q: What has no end, yet is surrounded by rope, especially when hoisting the sails?
  A: The ship’s mast.
• Q: What is always there but never seen, especially when guiding the ship’s passage?
  A: The current beneath the keel.
• Q: What can be as still as a rock, yet travels the world, especially when marked on a globe?
  A: The equator.
• Q: What has teeth but can’t bite, especially when securing the ship’s rigging?
  A: A turnbuckle.
• Q: What is full of holes but can hold a ship afloat, especially when it’s a net?
  A: The trawl.
• Q: What is always moving, yet never leaves the ship, especially when it’s a secret?
  A: The whisper of the wind.
• Q: What can be heard from afar, yet is silent on the deck, especially when it’s the call of a seagull?
  A: The ship’s bell.
• Q: What has branches but no leaves, especially when it’s a ship’s rigging?
  A: The mast.
• Q: What can be seen by all but touched by none, especially when it’s a rainbow at sea?
  A: A mirage.

• Question: What do you call a sailor’s favorite snack?
  
  Answer: A “seas-nack”!
• Question: Why did the sailor bring a ladder on the boat?
  
  Answer: To reach the high C’s!
• Question: What did the ocean say to the sailboat?
  
  Answer: Nothing, it just waved!
• Question: What kind of music do sailors listen to while sailing?
  
  Answer: Rock-n-roll!
• Question: Why did the sailor put on a life jacket before reading a book?
  
  Answer: Because it was “un-put-down-able”!
• Question: How does a sailor greet someone on their boat?
  
  Answer: “Ahoy there!”
• Question: What did the sail say to the wind?
  
  Answer: “I’m feeling a little “jibby” today!”
• Question: Why did the sailor bring a bar of soap on the boat?
  
  Answer: For a “wash and sail”!
• Question: How does a sailor start a race?
  
  Answer: With a “ready, set, row!”
• Question: Why did the sailor become an artist?
  
  Answer: He wanted to “sea-scape”!
• Question: What did the ocean say to the sailboat captain during the storm?
  
  Answer: “You’re in deep ship now!”
• Question: How does a sailor make their coffee?
  
  Answer: With “mainsail and steam”!
• Question: Why did the sailor take up gardening?
  
  Answer: To plant “sea-weed”!
• Question: What’s a sailor’s favorite type of movie?
  
  Answer: A “dramatic sailing adventure”!
• Question: How did the sailor fix the boat’s sail?
  
  Answer: With “patch and go”!
• Question: What’s a sailor’s favorite game to play on the boat?
  
  Answer: “Deck of Cards”!
• Question: What do you call a pirate who skips class?
  
  Answer: A “skipper”!
• Question: Why did the sailor bring a map to the bar?
  
  Answer: To “chart” a course for the night!
• Question: What did the buoy say to the sailboat?
  
  Answer: “You float my boat!”
• Question: Why did the sailor become a chef?
  
  Answer: He heard the food was “off the hook”!

Getting over with Sailing riddles

• Question: Why did the sailor bring string to the party?
  
  Answer: In case they needed to “tie one on”!
• Question: What did the sailboat say to the lighthouse?
  
  Answer: “You light up my voyage!”
• Question: How does a sailor apologize to the sea?
  
  Answer: With a “tide-y” gesture!
• Question: Why did the sailor take up photography?
  
  Answer: To capture “wave-lengths”!
• Question: What did the sailor say to the wind when it died down?
  
  Answer: “Don’t leave me “be-calm”!
• Question: Why was the sailboat always invited to parties?
  
  Answer: Because it knew how to “mast-er” the dance floor!
• Question: What did the sailor say when asked about navigation?
  
  Answer: “I’ve got it all figured “knot”!
• Question: Why did the sailor open a bakery?
  
  Answer: To make “sail-bread”!
• Question: How does a sailor stay warm in winter?
  
  Answer: With a “sailor-made” coat!
• Question: What did the captain say to the crew when they ran out of coffee?
  
  Answer: “This ship needs its “mornin’ jib”!
• Question: Why did the sailor go to school?
  
  Answer: To “learn the ropes”!
• Question: What’s a sailor’s favorite type of soup?
  
  Answer: “Clam Chow-“der”!
• Question: Why did the sailor bring a ladder to the beach?
  
  Answer: To climb aboard the “sand-schooner”!
• Question: How does a sailor make decisions?
  
  Answer: They “weigh anchor”!
• Question: What did the sailor say to the storm clouds?
  
  Answer: “You’re really “making waves” up there!”
• Question: Why did the sailor bring a pencil to the regatta?
  
  Answer: To “sketch” out a plan!
• Question: What’s a pirate’s favorite yoga pose?
  
  Answer: “Plank”!
• Question: How did the sailor pass the time on a windless day?
  
  Answer: By “knot-tying” practice!
• Question: Why did the sailor bring a belt to the boat?
  
  Answer: To keep his pants “sail-secure”!
• Question: What did the sailor say to the crab that stole his sandwich?
  
  Answer: “Give it back, that’s my “claw-stro” meal!