The Cannonball That Missed Drake: Two Attacks on San Juan, Read From the Garitas

Two English fleets came for San Juan within three years, and only one got in. Drake's 27 ships were turned back in 1595 by the fort and by the galleons anchored in the bay. In 1598 Cumberland took the city by landing east and attacking over land, then gave it up after roughly 65 days of dysentery.

1595: A fleet refused, a stool knocked over

Drake's approach was the obvious one: come by sea, aim at the harbor, and let the fleet do the work. The fort and the galleons in the bay answered it. The detail that survived four centuries is smaller than the battle. A cannonball entered the cabin of his flagship while he was at dinner, knocked the stool out from under him, and did not touch him. He left San Juan and died of illness later on the way to Panama. The shore had said no, and so had the sea.

1598: A landing east, and sixty-five days

Cumberland changed the question. His men came ashore east of the city and attacked over land, which kept them out of the arc of fire that had ruined Drake's plan. The city fell. Holding it was the harder problem: dysentery moved through the occupying force, and the English abandoned San Juan in about 65 days. Two attacks, two strategies, and one conclusion, the defenses were built to stop ships, not soldiers walking in from the east.

That is easiest to see standing at the garitas, the sentry boxes perched on the walls of El Morro. Most face the water. The landward side of the city needed a different answer, and got one later. For a later, civilian kind of stronghold, Ponce's Castillo Serrallés trades artillery for sugar money, and the island's twentieth-century military chapters are still visible on Culebra, where a tank sits on Flamenco Beach.

Doing it yourself

Go early or go late. The fort's gates typically open in the morning and close in the late afternoon, and the light is best before about 10 a.m., the National Park Service page for Castillo San Felipe del Morro carries the current schedule and entrance details. Stand on the upper battery near the lighthouse to see the bay mouth Drake needed, then walk the Paseo del Morro along the base of the walls to see how tall they actually are, that scale is what the brochure cannot give you. The eastern shoreline where Cumberland's force landed lies beyond the walls, best read from the top of the fort looking east.

A guided walls-and-garitas walk in Old San Juan runs about two hours and puts the dating and the geometry in order while you look at the harbor, from $40 (estimated). Traveler reviews on the activity page are the fastest way to tell which operators actually get inside the fort.