Drawings of galleons on the dungeon wall at Castillo San Cristóbal, San Juan National Historic Site

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Castillo San Cristóbal Main Page

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What is billed as the dungeon of Castillo San Cristóbal is a side chamber off of a tunnel that runs from the plaza de armas to the dry moat. To get to the dungeon, look for three tunnel entrances at the plaza—you can’t miss them. Take the left-hand tunnel, which is the longest in the fort. All three tunnels were built between 1766 and 1773.

Tunnel to the dungeon at Castillo San Cristóbal, San Juan National Historic Site

Tunnels were a great way for the Spanish soldiers to move between different areas of the fort without exposing themselves to enemy fire, but they were also a way in for enemy troops. As a precaution, alcoves in the tunnels were packed with gunpowder and could be exploded to collapse sections of the tunnel if enemies were on the verge of getting in. As you walk down the tunnel, notice the groves that run up the walls and across the ceiling. The section of tunnel between any two grooves is the section that would collapse if denotated. The Spanish did not want to collapse the entire tunnel because the fort above it would fall into what would essentially become a sink hole. However, there was still plenty of support if only one or two sections were collapsed.

Groves in the tunnel wall of a fort indicate a collapse point if this section of the tunnel were detonated

Tunnel underneath Castillo San Cristóbal, San Juan National Historic Site

In the San Cristóbal dungeon are drawings of Spanish galleons that were supposedly done by prisoners held here. One story has it that they were drawn by Puerto Rican mutineers who took control of a cannon at San Cristóbal and aimed it at the city, threatening to open fire if the Spanish did not leave. Another story claims they were drawn by a friar who was found guilty of murder and was chained to the wall for twenty years. And yet another says they were drawn by a Spanish captain who went crazy and mutinied. Who knows? The plaque at the entrance to the dungeon says it was a Spanish captain, though there is no accounting of his crime. All that can be said for sure is that there are drawings on the wall.

Room in the tunnel used as a dungeon at Castillo San Cristóbal, San Juan National Historic Site

Drawings of galleons on the dungeon wall at Castillo San Cristóbal, San Juan National Historic Site

In truth, there was no one location in the belly of San Cristóbal that was designated as a dungeon. Over the years, prisoners were held at various locations around the fort, including, if we are to believe the stories, the side chamber where the galleons are drawn. Even the National Park Service signage at the plaza identifies the left-hand tunnel as the one that leads to the dungeon.

If you continue all the way to the end of the tunnel, you will eventually come out on the roof of the 1942 Joint Operations Command Center. During World War II, both San Cristóbal and Castillo San Felipe del Morro became part of Fort Brooke. The JOC was the communications center for the fort and the headquarters of the Army’s Antilles Air Command, which directed air and naval forces in the Caribbean from the Bahamas to Antigua.

To get into the JOC, walk down the ramp to the structure at the far end of the grass-covered roof. This is an entrance—stairs or elevator—into the JOC. Here you will find some exhibits, restrooms, and a souvenir store. When done, instead of walking back up the stairs and returning to the plaza the same way you came, there is another tunnel you can take—the right-hand tunnel you saw at the plaza. Take this to complete a U-shaped journey through the lower level of San Cristóbal.

View of the left-hand tunnel and ramp from the rooftop entrance to the Joint Operations Command Center at Castillo San Cristóbal, San Juan National Historic Site

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