50 free Sailing trivia questions with answers — sports quiz, new questions added Aug 2026.
45 free Sailing trivia questions with answers. Sailing has its own vocabulary, its own heroes and a racing history stretching back to a schooner beating the Royal Yacht Squadron around the Isle of Wight in 1851. This quiz covers the lot: how sailors name the sides of a boat and why, the difference between a tack and a jibe, sloops versus ketches, what a keel actually does, and how fast a knot really is. Then it heads offshore for the America's Cup and the winged keel that ended a 132-year streak, Joshua Slocum, Robin Knox-Johnston and Ellen MacArthur going round the world alone, the Vendee Globe, the Sydney Hobart and Fastnet disasters, and the clipper era. Easy questions cover port and starboard and Boxing Day starts; the hard ones want the origin of the word spinnaker, the year the Beaufort scale was devised and which yacht set the Golden Globe's only finish. It works for weekend dinghy sailors, armchair Cup watchers and pub quiz teams alike. Every answer was checked against Wikipedia's articles on the boats, races and sailors involved, and each question carries the sentence that backs it up.
30 of 50 questions with answers and explanations. Play the quiz
Q 01Facing forward on a boat, where is starboard?
To your right
The name comes from Old English steorbord, the 'steer side', because early ships were steered with an oar on that side.
Q 02Why was the steering oar on early ships placed on the starboard side?
Most people are right-handed
The result was that ships docked on the opposite side, which became the 'port' or loading side.
Q 03What was the older name for the port side of a ship, changed in the 1500s?
Larboard
It came from 'ladebord' or loading side, and was dropped partly because it sounded too much like starboard when shouted.
Q 04Which manoeuvre turns a boat's bow through the wind so the wind moves to the other side?
Tacking
A series of them in a zig-zag lets a boat make progress toward a destination directly upwind.
Q 05A jibe (or gybe) turns which part of the boat through the wind?
The stern
An accidental one can send the boom swinging violently across the cockpit, which is why sailors call 'gybe-oh'.
Q 06Roughly how many degrees either side of the wind is a sailing craft's 'no-go zone'?
45
Sailing as close to that edge as possible is called beating, with the sails close-hauled.
Q 07A boat sailing at 90 degrees to the wind is on which point of sail?
Beam reach
At 135 degrees it becomes a broad reach, and at 180 degrees the boat is running.
Q 08The spar that runs along the foot of a mainsail to control its shape is called what?
The boom
Traditionally made of wood, they are now mostly aluminium or carbon fibre.
Q 09What is the line used to hoist a sail up the mast called?
Halyard
The name is a contraction of 'haul yard', from the days when it raised the yard rather than the sail itself.
Q 10The large balloon-like sail flown when sailing off the wind is thought to be named after which yacht?
Sphinx
The word's first recorded use came in 1866, a year after the yacht set hers in the Solent.
Q 11A sailboat with a single mast, one headsail and one mainsail is called what?
Sloop
It is by far the most common rig on modern cruising and racing yachts.
Q 12Which of these distinguishes a two-masted ketch from a yawl?
The mizzen is stepped forward of the rudder post
On a yawl the small mizzen sits aft of the rudder post, often right at the stern.
Q 13The triangular mainsail rig used on most modern yachts takes its name from which island?
Bermuda
It is also called the Marconi rig, because the tall stayed mast reminded people of early radio masts.
Q 21What informal nickname does the America's Cup trophy go by?
The Auld Mug
It is a bottomless sterling silver ewer made by Garrard & Co in 1848, three years before it was first raced for.
Q 22For how many years did the New York Yacht Club hold the America's Cup before losing it in 1983?
132
It remains the longest winning streak in the history of any sport.
Q 23What design innovation did the 1983 challenger that finally took the America's Cup use?
A winged keel
Designed by Ben Lexcen for Alan Bond's syndicate, the appendage was kept hidden under a skirt in the dock.
Q 14The word 'catamaran' comes from a word in which language?
Tamil
Kattumaram means 'logs bound together', although the craft itself was a raft rather than a twin-hulled boat.
Q 15Which seafaring peoples invented the catamaran and spread across the Indian and Pacific?
The Austronesians
Their crab-claw sails carried them from Taiwan as far as Madagascar and Easter Island.
Q 16One knot equals one nautical mile per hour, which is exactly how many kilometres per hour?
1.852
The name comes from the chip log, a knotted line paid out over the stern to measure speed.
Q 17A nautical mile was historically defined as one minute of what?
Latitude
That makes the Earth's polar circumference very close to 21,600 nautical miles.
Q 18Francis Beaufort, who devised the wind-force scale in 1805, was a naval officer serving which country?
Britain
Francis Beaufort's original scale described the effect of wind on a frigate's sails, not wind speeds.
Q 19The earliest known representation of a sail, from Egypt, dates to roughly when?
3100 BCE
The Nile's northward current and southerly prevailing wind made it an ideal place to invent sailing.
Q 20The America's Cup was first raced in 1851 around which island?
Isle of Wight
The schooner America beat 15 Royal Yacht Squadron yachts, and the trophy took her name.
Q 24Which American skipper lost the Cup in 1983 and won it back in 1987?
Dennis Conner
His loss and comeback were the basis of the 1992 film Wind.
Q 25The 2013 America's Cup was raced in which type of boat?
AC72 foiling wing-sail catamarans
Oracle Team USA came from far behind to keep the Cup in San Francisco.
Q 26Which syndicate won the America's Cup in 2017, then defended it in 2021 and 2024?
Emirates Team New Zealand
The 2024 defence took place in Barcelona, far from the Royal New Zealand Yacht Squadron's home in Auckland.
Q 27Who was the first person to sail single-handed around the world?
Joshua Slocum
His book Sailing Alone Around the World is a travel classic; he vanished at sea aboard the same boat in 1909.
Q 28What was the rebuilt oyster boat that completed the first solo circumnavigation in the 1890s called?
Spray
The 36-foot gaff-rigged sloop could famously hold a course for long stretches with nobody at the helm.
Q 29Who became the first person to sail solo, non-stop around the world, in 1969?
Robin Knox-Johnston
He was the only one of nine starters to finish the Sunday Times Golden Globe Race and gave his prize money to Donald Crowhurst's family.
Q 30How many of the nine entrants completed the 1968-69 Sunday Times Golden Globe Race?
One
The race is remembered for Donald Crowhurst's faked positions and apparent suicide, and it inspired the Vendee Globe.