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50 free Key West trivia questions with answers — geography quiz, new questions added Aug 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.
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Q 01Key West holds which geographic distinction among cities in the contiguous United States?
Southernmost
It sits about 130 miles southwest of Miami and roughly 95 miles north of Cuba at the end of the Florida Keys.
Q 02Key West's original Spanish name, Cayo Hueso, literally means what?
Bone cay
Legend says the island was littered with the bones of earlier native inhabitants who used it as a communal graveyard.
Q 03Key West is the county seat of which Florida county?
Monroe
The county covers most of the Florida Keys and part of the Everglades; the city's motto is 'One Human Family'.
Q 04Which famous roadway has its southern terminus in Key West?
U.S. Route 1
Mile-marker numbering on the Overseas Highway starts at 0 in Key West and runs up to 106 at Key Largo.
Q 05What is Key West's main commercial street, running from the Gulf to the Atlantic?
Duval
It is only 14 blocks long, which makes 'walking the Duval crawl' from one body of water to the other a local ritual.
Q 06Which Spanish conquistador led the first recorded European expedition past Key West, in 1513?
Juan Ponce de León
No settlement followed; the island passed between Spanish and British control for three centuries with almost no permanent residents.
Q 07Before selling Key West to John Simonton in 1821, to whom had Juan Pablo Salas already sold it for a sloop?
An ex-governor of South Carolina
General John Geddes lost the dispute; Simonton had friends in Washington and secured clear title.
Q 08When Lt. Matthew Perry planted the U.S. flag on Key West in 1822, what new name did he give it?
Thompson's Island
The name honoured Navy Secretary Smith Thompson; the harbour became Port Rodgers. Neither name stuck.
Q 09Sitting on the deep lane between the Atlantic and the Gulf, the 19th-century island was the 'Gibraltar of the' what?
West
That strategic value is why the U.S. Navy has kept a base there ever since.
Q 10By the 1830s, which industry made Key West the wealthiest US city per capita?
Wrecking (ship salvage)
Ships kept piling onto the reef, and salvage courts in Key West awarded the wreckers a share of every cargo saved.
Q 11Which side held Key West throughout the American Civil War, even though Florida seceded?
The Union
Fort Zachary Taylor and the naval base kept it in federal hands, and it became a haven for escaped enslaved people.
Q 12Refugees from Cuba's Ten Years' War made Key West a major producer of what in the late 1800s?
Cigars
The Great Fire of 1886 destroyed 18 factories, and many owners decamped to Ybor City in Tampa instead of rebuilding.
Q 13Which U.S. warship sailed from Key West to Havana in 1898, where it blew up?
USS Maine
Crewmen are buried in Key West and the Navy's inquiry into the blast was held at the Key West Customs House.
Q 21A native-born Key Wester is called a 'Conch'. What is a 'Freshwater Conch'?
A seven-year resident
The nickname came from Bahamian settlers, who supposedly vowed to 'eat conch' before paying the Crown's taxes.
Q 22What does the famous concrete buoy at South and Whitehead Streets claim, though not quite accurately?
Southernmost point in the continental U.S.
Whitehead Spit and Ballast Key both lie farther south, and its '90 miles to Cuba' overstates the gap; it is still the most photographed spot in the Keys.
Q 23Which of these did Hemingway write while living at 907 Whitehead Street, 1931 to 1939?
To Have and Have Not
Q 14The Overseas Railroad that reached Key West in 1912 extended which tycoon's railway?
Henry Flagler
Critics called it 'Flagler's Folly'; the Standard Oil co-founder rode the first train into town himself, aged 82.
Q 15Which airline, founded in Key West in 1926 to fly passengers to Havana, grew into America's flag carrier?
Pan Am
Within a year it held the U.S. Post Office contract for the Key West–Havana mail route.
Q 16The 1935 Labor Day Hurricane wrecked the Overseas Railroad. What replaced it?
An automobile highway
The state bought the roadbed and bridges for $640,000, and old rails were painted white and reused as guardrails.
Q 17Which US president spent 175 days at the Key West 'Little White House'?
Harry S. Truman
He made 11 visits, hosting cabinet members for fishing and poker; the town renamed Division Street in his honour.
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 stunt protested a Border Patrol roadblock on the only road out; Independence Day is still celebrated every April 23.
Q 20How did the newly declared micronation of Key West 'wage war' on the United States in 1982?
Broke stale Cuban bread over a sailor's head
It surrendered after one minute and applied for a billion dollars in foreign aid; the roadblock was removed soon after.
He also finished 'The Snows of Kilimanjaro' and 'Green Hills of Africa' in the writing studio above the carriage house.
Q 24The cats that still roam the Hemingway House are famous for what physical trait?
Extra toes
They descend from a six-toed ship's cat named Snowball; many still carry the polydactyl gene.
Q 25What did Hemingway press into the wet cement beside his new swimming pool after hearing how much it cost?
A penny
'Take the last penny I've got,' he supposedly said; the pool was the first in the Keys and Pauline had paid for it herself.
Q 26Hemingway's nickname 'Papa' came from a fishing crowd that included Joe Russell, better known by what name?
Sloppy Joe
Russell's bar, Sloppy Joe's, has hosted a Hemingway look-alike contest every July since 1980.
Q 27Which playwright drafted 'A Streetcar Named Desire' at Key West's La Concha Hotel in 1947?
Tennessee Williams
Unlike Hemingway's grand house, Williams's home at 1431 Duncan Street was a modest bungalow in New Town.
Q 28Mallory Square is famous for a nightly celebration of what?
The sunset
It begins two hours before sunset every day; when a cruise pier opened in 1984, an ordinance ordered ships out of port before it started.
Q 29Fantasy Fest, Key West's costumed street party, is held in the last week of which month?
October
It was started in 1979 to fill the slow season; floats carry an elected Conch King and Queen.
Q 30Why is the filling of a genuine Key lime pie pale rather than green?
Ripe Key limes are yellow
The pie probably descends from a 1931 Borden condensed-milk brochure recipe; the 'Aunt Sally' invention story dates only to 1995.