Come and explore the second oldest city in the Western Hemisphere. Old San Juan is actually an island connected to the main island by bridges on the eastern side. The oldest section is on the west side and walled in on 3 sides. The historic city is divided into seventeen square blocks.

The northern side of the city is uphill and is comprised of the residential area of town. The southern part, or port area (ports 1-4), is the commercial and tourist section that is comprised of shops, piers, and most of the restaurants. The city’s eastern side is protected by Fort San Cristobal. The western area of the city contains Paseo dela Princesa, La Fortaleza (Governor’s Mansion) and Fort El Morro. It is the oldest area of town where you can find 300-450 year old homes and buildings.

Old San Juan, properly known as San Juan Antiguo, is the oldest city in the U.S. and its territories. The Spanish settled San Juan in 1521. It replaced “Caparra,” Puerto Rico’s first settlement, as the island’s capital.

Iggy’s Fun Facts
CNN report on Old San Juan’s food and history

When Christopher Columbus discovered the island in 1493, he named it San Juan Bautista (St. John the Baptist). The city later became known as Puerto Rico (meaning rich port). In the 1520’s the city’s name changed to San Juan and the island to Puerto Rico by a confused cartographer. The name changes never got corrected. San Juan quickly became an important Spanish colony and by 1530 San Juan had a hospital, university, and even a library!

It wasn’t long before San Juan gained the attention of other European countries and the first pirate attacks began in 1528 when the French razed the settlements around San Juan. To fend off pirate attacks from the French, Dutch, and English, the Spanish created two huge forts and walled-in the city.

Construction on El Morro Fort began in 1539.  It is an immense fort with 18-foot thick walls, dungeons, barracks, outposts, ramps, and mazes of tunnels that protected the city from foreign invasion. In 1634 construction began on the even larger Fort San Cristóbal to protect the city from the other direction. San Juan became Spain’s fortified door to the Americas. By the early part of the 16th century, San Juan had become the departure point for Spanish expeditions to explore and settle unknown parts of the new world.

San Juan continued to be an important strategic military location for the Spanish well into the 17th, 18th, and 19th centuries until 1898, when the U.S. attacked Puerto Rico during the Spanish-American War. Puerto Rico surrendered after a few skirmishes and eventually became a commonwealth of the United States.

Today Old San Juan is a busy hub for tourism. San Juan is the Caribbean’s main cruise port and is home to more than 28 different cruise lines which bring millions of tourists to the city each year. You can tour the entire 500 year old city on foot. The forts El Morro and San Cristóbal are open to tourists and many of the 16th and 17th century houses and buildings have been restored to their original architectural splendor and now house various museums filled with fascinating history and artifacts that tell the story of this old city.

  1. El Morro has only been seized once by pirates, but the siege lasted just a few days.
  2. Though the proper name is San Juan Antiguo, it is culturally known as Viejo San Juan.
  3. “En Mi Viejo San Juan” is probably Puerto Rico’s unofficial national anthem and most beloved song by composer Noel Estrada.
  4. Old San Juan has the smallest house in the world. Click here for more information and to see a picture.
  5. La Iglesia de San Jose is the oldest functioning church in the American territories. Constructed in 1522, the Golden Altar demonstrates a grand example of the care and detail of a proud community. The Legend says pirates invaded the island and the residents, terrified of the attackers stealing their beautiful altar, quickly painted it black in an effort to conceal the sacred symbol. Years later, the pirates gone and forgotten, the paint peeled. They removed the paint, cleaned the sanctuary, and restored it to its original state, surprised to find it was gold.
  6. Old San Juan is the filming site for scenes in many movies such as: Dirty Dancing, Havana Nights, The Rum Diaries, Amistad, Pirates of the Caribbean: Strange Tides, and Fast Five.
  7. Old San Juan is the film site of the pilot episode of the the 1970′s TV series, The Flying Nun.
  8.  Adoquine, a blue stone cast from furnace slag makes up the cobblestones that pave the streets. They were originally brought over as ballast on Spanish ships. Tin and moisture have given them their coloring.
  9. Another nickname of Old San Juan is “La Ciudad Amurrallada” which means the walled city.
  10. Old San Juan is the second oldest European settled city in the Americas, Santo Domingo being the first.
  11. Old San Juan boasts many famous people such as:
    • Manuel A. Alonso (writer)
    • José Julián Acosta (comedian)
    • Raul Julía (actor)
    • Juan “Chi-chi” Rodriguez (golfer)
    • José Compeche (painter)
    • José Enrique Pedreira (musician and composer.)
  12. The United Nations named six monuments in Old San Juan world-class historic sites.
  13. There are more than 400 restored buildings from the 16th and 17th centuries.
  14. The sentry boxes around the city where Spanish soldiers once stood guard become public restrooms at night.

Here is a report on Old San Juan’s food and history: