Late 16th Century
Before and after its regulation in 1565, many ships from the flotas system called
at San Juan to load water and victuals upon arrival in the Caribbean. Two of the three main Spanish routes into
the New World passed by Puerto Rico, through either the Mona or the Anegada passages. The shipwrecks from this
period have attracted the interest of treasure-hunters since the end of the Second World War, and some-mostly when
found in shallow waters-may have been heavily looted.
Plagued by attacks from French pirates and privateers since its founding, San
Juan quickly became a fortified city, responding to the latest developments in warfare and naval capability. Mainly
developed in Italy, but quickly adopted by all European powers, improved ship and gun designs changed the way nations
waged war in the late-16th century and forced the development of new fortifications and defensive strategies everywhere,
including in Puerto Rico.
During the second half of the 16th century, Spanish power suffered from over-extension
and economic stagnation. This depression was felt across the Atlantic, affecting the economies of Puerto Rico and
the rest of Spain's colonial empire. Concurrent with Spain's fall was the rise of English maritime power. Although
often exaggerated in British literature, the success of English privateers, such as Francis Drake and John Hawkins,
forced a re-assessment of the Spanish defensive system in the New World. Between the late-16th and the late-18th
centuries San Juan suffered four major attacks by English and Dutch forces.
In 1595 Francis Drake and John Hawkins led an English assault on Puerto Rico.
Their fleet is said to have anchored near the Punta Palo Seco, off Isla de Cabras. Although the English succeed
in burning a number of Spanish ships lying at anchor in San Juan Bay, the conquest attempt failed. According to
Spanish accounts, Hawkins lost his life at Puerto Rico, and Drake lost many men and a small number of ship's boats.
These shipwrecks may have been almost entirely dredged during the late-19th and early-20th centuries.
Another attempt to take San Juan was carried out three years later, in 1598, by
the 3rd Earl of Cumberland, George Clifford. His fleet anchored off Playa de Cangrejos and landed a large expeditionary
force, which succeeded in capturing the fort of San Felipe del Morro, but it was not held for long, however. After
only a short sojourn, the Earl of Cumberland abandoned his plans and left the island for good.