Castillo San Cristóbal is an old colonial age fort located in San Juan, the capital of Puerto Rico, which was part of the defensive fortifications built by the Spanish to protect the city. It is different from other fortifications built in Puerto Rico at the time as it was designed to defend against attack by land; most other defenses were concerned with possible attacks by sea.
This castle was the biggest defensive fortification of any kind built in the New World by the Spanish conquistadors. In it’s original and first form, completed in 1783, it covered around 27 acres and pretty much walled off all of San Juan. Many guard towers kept a constant eye on the city and it’s vicinity, and entry was possible only through the castle’s big double gates.
Colonial fortification of the island of Puerto Rico dates back to 1634 when the first small defensive turret was built north of San Juan. With it starts the story of Castillo San Cristóbal: the small redoubt was named after the high ground it was built on — San Cristóbal. More than a century later, in 1765, the watchtower with small walls around it was extended. A much larger area was enclosed with stone walls that were much higher than before. Platforms for cannons were installed and for the first time San Cristóbal started to look a bit more like a serious defense structure.
When Carlos III came to the throne in 1759 he ordered extension of the existing fortress in San Juan. His Marshal, Alexander O’Reilly, and engineers Juan Francisco Mestre and Colonel Tomás O’Daly took the task. The order was to completely separate the town from it’s surroundings with high walls, cannon platforms, and outpost towers. The war with England was around the corner and Puerto Rico was to remain a territory of the Spanish Kingdom. In the small period they had prior to the war, the engineers successfully completed the fort La Contraguardia de la Trinidad. During the war they completed another fort to the east named El Albanico and a battery named La Princesa, which was close to the sea where it could repel any incoming naval attacks. By the time King Carlos III died in 1788, his orders were almost completely finished. The Spanish successfully and most effectively protected their colony from hundreds of ships carrying more than seven thousand English soldiers.
After the Anglo-Spanish war ended, a long period of peace and prosperity for Puerto Rico and most of the other New World colonies followed. The New World was growing so fast, San Juan included, that the government of San Juan decided to tear down a section of the great castle in 1897 in order to ease the passage of traffic in and out of the capital.
There is a scary legend about one of the castles many sentry boxes or lookouts (small rooms that served as checkpoints throughout the outer wall). This one is called “La Garita del Diablo” which translates as “The Devil’s Lookout” and it is told that many soldiers disappeared while on guard duty on this particular lookout. However, history remembers only one case of this kind; the soldier’s name was Sánchez and his disappearance wasn’t mysterious in particular. He voluntarily jumped from Devil’s Lookout and deserted his duties to join his beloved girlfriend. The Devil’s Lookout is off limits to the public to this day.