Sailing Trivia
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99 free Sailing trivia questions with answers — sports quiz, new questions added Oct 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 99 questions with answers and explanations. Play the quiz
Q 01Facing forward on a boat, where is starboard?
To your right
To your right is starboard, from Old English steorbord, the 'steer side', because early ships were steered with an oar held over that side.
Q 02Why was the steering oar on early ships placed on the starboard side?
Most people are right-handed
Most people are right-handed, so a helmsman at the stern held the steering oar on the right; ships then docked on the opposite side, which became the loading or 'port' side.
Q 03What was the older name for the port side of a ship?
Larboard
Larboard came from 'ladebord', the loading side; the Royal Navy replaced it with 'port' in 1844 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
Tacking turns the bow through the wind; a series of tacks in a zig-zag lets a boat make progress toward a destination directly upwind.
Q 05What is the lowest inside part of a hull, where water collects, called?
Bilge
Bilge is the lowest inside part of the hull, where water and spills collect; a bilge pump clears it overboard.
Q 06Roughly how many degrees either side of the wind is a sailing craft's 'no-go zone'?
45
45 degrees either side of the wind is the usual no-go zone; 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
Beam reach is the point of sail at 90 degrees to the wind; at about 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
The boom is the spar along the foot of the mainsail; traditionally wood, booms are now mostly aluminium or carbon fibre.
Q 09What is the line used to hoist a sail up the mast called?
Halyard
Halyard is a contraction of 'haul yard', from the days when the line 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
Sphinx, a yacht that set such a sail in the Solent in 1865, is the usual origin given for 'spinnaker'; the word's first recorded use came in 1866.
Q 11A sailboat with a single mast, one headsail and one mainsail is called what?
Sloop
Sloop is by far the most common rig on modern cruising and racing yachts: one mast carrying a mainsail and a single headsail.
Q 12Which of these distinguishes a two-masted ketch from a yawl?
The mizzen is stepped forward of the rudder post
The mizzen is stepped forward of the rudder post on a ketch; on a yawl the smaller 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
Bermuda gave its name to the rig, which 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
The Auld Mug 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
132 years, from 1851 to 1983, was the New York Yacht Club's hold on the Cup, often described as the longest winning streak in sport.
Q 23What design innovation did the 1983 challenger that finally took the America's Cup use?
A winged keel
A winged keel, designed by Ben Lexcen for Alan Bond's Australia II syndicate, was kept hidden under a skirt at the dock.
Q 14The word 'catamaran' comes from a word in which language?
Tamil
Tamil kattumaram means 'logs bound together'; the original craft was a raft of lashed logs rather than a twin-hulled boat.
Q 15Which seafaring peoples invented the catamaran and spread across the Indian and Pacific Oceans?
The Austronesians
The Austronesians built the twin-hulled and outrigger canoes whose 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
1.852 km/h is exactly one knot because the international nautical mile was fixed at 1,852 metres in 1929; the name comes from the chip log, a knotted line paid out to measure speed.
Q 17A nautical mile was historically defined as one minute of what?
Latitude
Latitude is measured in degrees and minutes of arc along a meridian, and one such minute was the nautical mile; that makes the Earth's polar circumference 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
Britain's Royal Navy was Beaufort's service; his original 1805 scale described the effect of wind on a frigate's sails rather than wind speeds.
Q 19The earliest Egyptian depiction of a boat under sail dates to roughly when?
3100 BCE
3100 BCE is roughly the date of the painted Egyptian pot showing a boat under sail; the Nile's northward current and southerly prevailing wind made it an ideal place to develop sailing.
Q 20The America's Cup was first raced in 1851 around which island?
Isle of Wight
Isle of Wight was circled in the 1851 race in which the schooner America beat a fleet of 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
Dennis Conner lost the Cup with Liberty in 1983 and won it back with Stars & Stripes 87 off Fremantle; the 1992 film Wind was loosely based on the story.
Q 25The 2013 America's Cup was raced in which type of boat?
AC72 foiling wing-sail catamarans
AC72 foiling wing-sail catamarans were the 2013 boats; Oracle Team USA came back from 1-8 down to win 9-8 and 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
Emirates Team New Zealand beat Oracle in 2017, then defended in Auckland in 2021 and Barcelona in 2024, far from the Royal New Zealand Yacht Squadron's home.
Q 27Who was the first person to sail single-handed around the world?
Joshua Slocum
Joshua Slocum finished the voyage in 1898; his book Sailing Alone Around the World is a travel classic, and 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
Spray, 36 feet long and gaff-rigged, 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
Robin Knox-Johnston was the only one of nine starters to finish the Sunday Times Golden Globe Race, and he gave his prize money to Donald Crowhurst's family.
Q 30Which Golden Globe Race sailor abandoned the race while well placed and sailed on to Tahiti?
Bernard Moitessier
Bernard Moitessier, in a strong position to win, turned away from the finish and kept sailing to Tahiti, a voyage he recounted in The Long Way.