San Juan, Puerto Rico
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50 free San Juan, Puerto Rico trivia questions with answers — geography quiz, new questions added Oct 2026.
San Juan packs five centuries into a few square miles. The capital of Puerto Rico grew up behind massive stone walls, fought off fleets from rival empires, and still wakes each morning to streets paved in blue. It is also a modern Caribbean city of beaches, universities, arenas and all-night street parties. This quiz turns the best fun facts about San Juan into questions. Expect the forts of the old city and the sieges they survived, the legends locals still tell, the neighborhoods beyond the walls, and the festivals, drinks, ballplayers and movie stars the city has given the world. It suits travelers planning a trip, students of Caribbean history, and anyone with Puerto Rican roots who wants to test what they know. Every answer comes with a short explanation, so you leave with a story to tell.
30 of 50 questions with answers and explanations. Play the quiz
Q 01Mayor Felisa Rincón de Gautier had planeloads of what flown to San Juan for children in the 1950s?
Snow
Snow arrived by plane in 1952, 1953 and 1954 so that children who had never seen it could play in it. Doña Fela was also the first woman mayor of a capital city in the Americas.
Q 02Old San Juan's seaside barrio La Perla drew curious tourists after featuring in which 2017 music video?
Despacito
Despacito, by Luis Fonsi and Daddy Yankee, was filmed in La Perla and has drawn billions of YouTube views. The barrio was built just outside the old city walls.
Q 03Which Oscar-winning Hollywood actor was born in San Juan in 1974 under the family surname Bottom?
Joaquin Phoenix
Joaquin Phoenix was born Joaquin Rafael Bottom in a San Juan hospital in October 1974. He went on to win the Best Actor Oscar for playing the title role in Joker.
Q 04Which New York Giants star played beside Roberto Clemente for San Juan's Santurce club in winter 1954–55?
Willie Mays
Willie Mays arrived as the National League MVP and won the Puerto Rican league's MVP award and batting title too. That Santurce roster was nicknamed the Panic Squad.
Q 05At midnight on the Noche de San Juan, what do Puerto Ricans traditionally do at the beach?
Fall backward into the sea
Fall backward into the sea, and do it three, seven or twelve times: that is the midnight ritual. Any water will do, and some people settle for a river, a lake or even a bathtub.
Q 06A San Juan hotel and a local restaurant each claim to have invented which rum cocktail in the mid-1900s?
Piña colada
Piña colada is claimed by the Caribe Hilton, for bartender Ramón Marrero in 1954, and by the restaurant Barrachina, for 1963. Puerto Rico proclaimed it the official drink in 1978.
Q 07Spanish colonists first called the city of San Juan 'Puerto Rico', a name that means what in English?
Rich port
Rich port was the city, while the island carried the saint's name. Traders came to use the harbor's name for the whole island, and the two names traded places.
Q 08The blue cobblestones of Old San Juan first crossed the Atlantic in Spanish ships, serving as what?
Ballast
Ballast kept the lightly loaded ships stable on the voyage out. The stones were unloaded in San Juan and road builders laid them as paving; the slag turns blue with age and exposure.
Q 09Which animals around San Juan's El Morro fortress did the National Park Service plan to remove in 2023?
Stray cats
Stray cats, about 200 of them, are thought to descend from animals brought in to keep down rats. The removal plan was paused after a cat-welfare group sued.
Q 10Which Old San Juan building is the oldest executive mansion still in use anywhere in the Americas?
La Fortaleza
La Fortaleza has housed Puerto Rico's governors since the 16th century. It began in the 1530s as the first fort the Spanish built to defend San Juan Bay.
Q 11The windy lawn in front of San Juan's El Morro fortress is a favorite spot for which pastime?
Kite flying
Kite flying fills the lawn on windy days, alongside picnics and stargazing. In the early 1900s the US military had covered the same ground with baseball diamonds and a golf course.
Q 12San Juan takes its name from which saint, whose name Christopher Columbus first gave to the whole island?
John the Baptist
John the Baptist was honored when Columbus named the island San Juan Bautista on his second voyage in 1493. Puerto Rico still marks the saint's feast with a night-long party each June.
Q 13Which MLB team played part of its 2003 and 2004 home schedule at San Juan's Hiram Bithorn Stadium?
Q 21A fleet of which nationality, under a captain the Spanish called Balduino Enrico, burned San Juan in 1625?
Dutch
Dutch ships, 17 of them, took the town but could not take El Morro, so the attackers burned San Juan as they withdrew. Their commander's own name was Boudewijn Hendricksz.
Q 22The Earl of Cumberland's English force seized San Juan in 1598 but left within months, driven out by what?
Dysentery
Dysentery crippled hundreds of his men, so the English gave up the city and sailed home. It was the only time El Morro was taken in battle.
Q 23Which San Juan fortress, built to stop attacks by land, is the largest Spain built in the New World?
San Cristóbal
Montreal Expos
Montreal Expos games in San Juan used field dimensions set to match Olympic Stadium back home. After 2004 the club moved to Washington and became the Nationals.
Q 14Shots from San Juan's El Morro at a German ship are widely regarded as America's first in which war?
World War I
World War I had not yet drawn in the United States when Lt. Teófilo Marxuach opened fire on the Odenwald, an unarmed merchant ship trying to leave San Juan Bay without permission.
Q 15San Juan is recognized as the epicenter of which music genre, which took off there as underground music in the 1990s?
Reggaeton
Reggaeton took shape in the city's underground scene from hip-hop, local urban beats and Panama's Spanish-language reggae. San Juan natives such as Daddy Yankee then carried it around the world.
Q 16San Juan is home to El Gran Combo, a band nicknamed 'the university' of which dance music genre?
Salsa
Salsa has one of its world capitals in San Juan, which has served as the home of the World Salsa Congress since the late 1990s.
Q 17The San Sebastián Street Festival in Old San Juan each January unofficially marks the end of which season?
Christmas
Christmas celebrations in Puerto Rico run deep into January, and La SanSe is their unofficial last party, drawing more than 200,000 people. It began as a street's feast for Saint Sebastian.
Q 18Old San Juan occupies the western end of what kind of landform, joined to the rest of the city by bridges?
An islet
An islet called the Isleta de San Juan holds the old city, linked to the main island by two bridges and a causeway. The site guards the mouth of San Juan Bay.
Q 19Which Spanish explorer, tied by legend to the Fountain of Youth, is entombed in Puerto Rico's capital?
Juan Ponce de León
Juan Ponce de León died in Havana in 1521; his remains lay in San Juan's San José Church from 1559 until 1836 and were later moved to the cathedral. Historians treat the fountain story as a myth.
Q 20San Juan's gunners put a cannonball through the flagship cabin of which English sea captain in 1595?
Francis Drake
Francis Drake was beaten off after defenders drew a metal chain across the entrance to San Juan Bay to keep his fleet out. He never took the city.
San Cristóbal reached its full size in 1783, after earlier invaders had twice taken the city from its landward side. It rises about 150 feet above the shoreline.
Q 24The garitas that jut from Old San Juan's walls, now a symbol of the city, are what?
Sentry boxes
Sentry boxes gave lookouts a view along the walls and out to sea. The most famous, the Garita del Diablo, comes with legends of soldiers who disappeared from inside it.
Q 25In 1983, the Spanish forts and walls of Old San Juan received which international designation from UNESCO?
World Heritage Site
World Heritage Site status covers the forts, the surviving walls and the governor's mansion together. It was the eleventh such listing in the United States.
Q 26Puerto Rico's marble-clad Capitol in San Juan was designed to resemble which ancient Roman building?
The Pantheon
The Pantheon was the model for architect Rafael Carmoega, who also took inspiration from the Low Memorial Library in New York City. Mosaics decorate the ceiling of the Capitol's dome.
Q 27San Juan's Condado Vanderbilt Hotel of 1919 was designed by the architects of which New York City landmark?
Grand Central Terminal
Grand Central Terminal and the hotel both came from the firm Warren and Wetmore. The hotel still stands on Ashford Avenue in the beachfront Condado district.
Q 28The 1937 tower of the University of Puerto Rico's main San Juan campus is named for which US president?
Franklin Roosevelt
Franklin Roosevelt took an interest in the building of the university, so the tower was christened in his honor. On campus it is known simply as La Torre.
Q 29Which Cuban-founded rum maker runs the world's largest rum distillery across the bay from Old San Juan?
Bacardi
Bacardi bought its land in Cataño in 1958, and Puerto Rico's governor dubbed the plant the Cathedral of Rum. A ferry links Cataño with Old San Juan.
Q 30San Juan began in 1508 as which low-lying, swampy settlement before its colonists moved to the present site?
Caparra
Caparra was named after an abandoned Roman village in Spain, and its foundations survive in neighboring Guaynabo. Trouble with health, defense and supplies pushed the settlers out by 1521.