Key West Trivia
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49 free Key West trivia questions with answers — geography quiz, new questions added Oct 2026.
46 free Key West trivia questions with answers. Key West packs a lot of story into four square miles: an island called 'bone cay' that was sold twice by the same man, a wrecking boom that made it the richest town per capita in America, a Civil War outpost that never fell, a cigar capital, a Navy town, and finally the end-of-the-road playground of Hemingway, Truman, Tennessee Williams and Jimmy Buffett. This quiz covers all of it, plus the things every visitor asks about: the Conch Republic's one-minute war, the six-toed cats, the penny in Hemingway's pool, the sunset ritual at Mallory Square, Fantasy Fest, Key lime pie, the Atocha treasure and the Overseas Highway that replaced Flagler's railroad. About a third of the questions are easy enough for a first-time visitor; the rest will test a lifelong Conch. Every answer has been checked against a primary source, mostly Wikipedia's Key West and Florida Keys articles, and each question shows its citation.
30 of 49 questions with answers and explanations. Play the quiz
Q 01The U.S. Navy first set up a base at Key West in 1823 to drive out which enemy?
Caribbean pirates
Caribbean pirates. Commodore David Porter hunted them through the West Indies with a squadron of shallow-draft schooners and barges, yet by 1826 the Navy had already moved its base north to Pensacola.
Q 02Key West's original Spanish name, Cayo Hueso, literally means what?
Bone cay
Bone cay. In the usual telling, Spanish visitors found the island strewn with the bones of earlier native inhabitants, who are said to have used it as a communal graveyard.
Q 03Key West is the county seat of which Florida county?
Monroe
Monroe County also takes in a huge slice of the mainland Everglades, most of its land, yet almost nobody lives there: nearly all of its people are out on the Keys.
Q 04Which famous roadway has its southern terminus in Key West?
U.S. Route 1
U.S. Route 1 starts at mile marker 0 in Key West and runs some 2,370 miles to the Canadian border; out along the Keys, street addresses simply follow the nearest mile marker.
Q 05What is Key West's main commercial street, running from the Gulf to the Atlantic?
Duval
Duval Street crosses the whole island in just 14 blocks, and bar-hopping from one end to the other is a ritual known as the Duval Crawl.
Q 06Which Spanish conquistador led the first recorded European expedition past Key West, in 1513?
Juan Ponce de León
Juan Ponce de León named the whole island chain Los Mártires, the Martyrs, because from a distance the islands looked to him like suffering men.
Q 07Which independence hero raised money and recruits among Key West's exiles for a war against Spain?
José Martí
José Martí made repeated trips in the early 1890s to unite the island's divided Cuban exiles, and the Cuban Revolutionary Party he founded took shape during those visits.
Q 08Which naval officer raised the U.S. flag over Key West in 1822?
Matthew C. Perry
Matthew C. Perry, then a lieutenant commanding the schooner Shark, renamed the island Thompson's Island after the Navy secretary, a name that never stuck; three decades later he opened Japan to American trade.
Q 09Which naturalist's visit to Key West in the 1830s is honoured by a house museum and tropical garden there?
John James Audubon
John James Audubon drew Keys birds for The Birds of America on that trip. The house named for him was due for demolition in 1958, and its rescue is credited with sparking the island's restoration movement.
Q 10Which trade made Key West a wealthy town in the first half of the 19th century?
Salvaging shipwrecks
Salvaging shipwrecks, known as wrecking, was licensed work: from 1828 a U.S. court sitting in Key West decided what share of each rescued cargo the wreckers could keep.
Q 11Which fort let Union troops hold Key West throughout the Civil War, even though Florida had seceded?
Fort Taylor
Fort Taylor was occupied at midnight on January 13, 1861 by a Union captain acting without orders, and it went on to serve as a base against Confederate blockade runners.
Q 12Refugees from Cuba's Ten Years' War made Key West a major producer of what in the late 1800s?
Cigars
Cigars. Whole factories moved over from Cuba, and before long Spanish was the island's second language and a son of Cuban independence leader Carlos Manuel de Céspedes was its mayor.
Q 13Which U.S. warship sailed from Key West to Havana in 1898, where it blew up?
USS Maine
Q 21In Key West, where natives are called 'Conchs', who earns the title 'Freshwater Conch'?
A seven-year resident
A seven-year resident. 'Conch' is thought to have begun as a put-down, and the islanders who inherited the name turned it into a title that newcomers now have to earn.
Q 22What does Key West's famous painted concrete buoy claim to mark, a boast that is slightly off?
Southernmost point in the continental U.S.
'Southernmost point in the continental U.S.' is a stretch: Navy land on the island reaches farther south, and the real record belongs to Ballast Key, a small island out to the west.
Q 23Which Hemingway novel, written at his Whitehead Street house in the 1930s, is set in Key West itself?
USS Maine exploded three weeks after reaching Havana, a loss that helped push the United States into war with Spain; some of her dead are buried in the Key West Cemetery.
Q 14The Overseas Railroad that reached Key West in 1912 extended which tycoon's railway?
Henry Flagler
Henry Flagler, the Standard Oil co-founder, was 82 and nearly blind when he rode the first train into Key West in January 1912; he died the following year.
Q 15Which airline began in 1927 by flying mail from Key West to Havana?
Pan Am
Pan Am won the Key West to Havana mail contract in 1927 and carried its first passengers between the two a year later; within a decade its flying-boat Clippers were crossing the Pacific.
Q 16What replaced the Overseas Railroad after a 1935 hurricane wrecked it?
An automobile highway
An automobile highway. The state bought the wrecked line's roadbed and surviving bridges and laid a road on top, so from 1938 drivers could reach Key West without the old ferry crossing.
Q 17Which US president spent 175 days at the Key West 'Little White House'?
Harry S. Truman
Harry S. Truman first came in November 1946 for a rest in the sun and kept coming back, governing between fishing trips and poker games at a table built for him.
Q 18Which inventor lived in the Little White House during World War I, perfecting underwater weapons?
Thomas Edison
He reportedly worked up 41 underwater weapons in six months; the first presidential visitor to the house was Taft in 1912.
Q 19In 1982 Key West staged a mock secession from the United States, declaring itself what?
The Conch Republic
The Conch Republic was a protest: a Border Patrol roadblock on the only road out was scaring off visitors, and Key West still celebrates its 'independence' every April 23.
Q 20What did Key West's mock rebels use as ammunition when they 'declared war' on the United States in 1982?
Stale Cuban bread
Stale Cuban bread was the rebels' weapon. Their 'prime minister', the mayor, then surrendered and asked the United States for foreign aid, and the roadblock that started it all was quietly removed.
To Have and Have Not
To Have and Have Not follows a Key West boat captain driven to smuggling by the Depression; the 1944 Bogart and Bacall film kept the title but moved the story to Martinique.
Q 24The cats that still roam the Hemingway House are famous for what physical trait?
Extra toes
Extra toes. The museum says its cats descend from Snow White, a white six-toed cat a ship's captain gave Hemingway; about half show the trait, though all carry the gene.
Q 25Which coin is set in the cement beside Hemingway's Key West swimming pool, a souvenir of his fury at its cost?
A penny
A penny. The pool cost $20,000 in the 1930s, and Hemingway is said to have produced the coin and told his wife Pauline she might as well take his last cent too.
Q 26Which Key West bar, run by Hemingway's fishing companion, was his 1930s haunt?
Sloppy Joe's
Sloppy Joe's was run by Joe Russell, who took Hemingway fishing; every July the bar now fills with bearded hopefuls for its Hemingway look-alike contest.
Q 27Which playwright kept a modest Key West bungalow as his home until his death in 1983?
Tennessee Williams
Tennessee Williams is believed to have worked on A Streetcar Named Desire at the island's La Concha Hotel in 1947, before settling into the house that was his home for more than thirty years.
Q 28Mallory Square is famous for a nightly celebration of what?
The sunset
The sunset gets a round of applause from the crowd as it sinks into the Gulf, the finale of a nightly dockside show of jugglers, musicians and craft stalls.
Q 29Why is the filling of a genuine Key lime pie pale rather than green?
Ripe Key limes are yellow
Ripe Key limes are yellow: the fruit is usually picked green but yellows as it ripens, and its juice is yellow too, so a filling made the classic way never turns green.
Q 30Key lime pie is Florida's official state pie, but which berry dessert became the state dessert in 2022?
Strawberry shortcake
Strawberry shortcake got the title at a bill-signing held at Plant City's strawberry festival, where it is the signature dish; Key lime pie kept its own crown as state pie.