Dungeons, dark tunnels and a haunted watchtower make this Spanish fort worthy of exploration
Once referred to as the Gibraltar of the West Indies, Castillo San Cristobal is the largest fortress ever built by the Spanish in the Western Hemisphere. Construction of this sprawling hilltop fortification took more than 150 years, and its outer walls once encircled the original city of San Juan. Though portions of the fortress walls were demolished to allow modern roadways to enter the historic walled city, the main 27-acre grounds of this Colonial-era landmark remain intact, and are now a World Heritage site.
Though impressive, the grounds of San Cristóbal see far fewer visitors than nearby Castillo San Felipe del Morro—the iconic fortress that overlooks the entrances to San Juan Harbor at the western end of Old Town. Those who do tour Castillo San Cristóbal find it well worth the visit. Now under the care of the U.S. Park Service, the grounds are rich in history, and include five massive garrisons, dungeons, powder magazines and a network of dry moats connected by a labyrinth of tunnels, all of which can be explored.
Any tours should also include a visit to the garitas—the stone century boxes that provide panoramic views of sea and city. The most famous of these is the Garita del Diablo (Sentry Box of the Devil). According to legend, guards stationed at that post would disappear, as if taken away by the devil. Of course, it’s more likely that they simply seized the opportunity to slip away from this remote watchtower and take unofficial leave at a nearby waterfront tavern.