Viejo San Juan

The capital of Puerto Rico, San Juan ranks high on the list of most  historic cities in the New World, with early explorers establishing a  settlement there 15 years after Columbus’s monumental first voyage. The city has been the scene of many historic events, from naval battles to pirate attacks. Modern San Juan, now a top Caribbean tourism destination, embraces its long and fascinating history.     

Early Settlement  

The first settlement on the island of Puerto Rico was Caparra, founded in 1508 by Juan Ponce de León, a Spanish explorer and conquistador best remembered for his quixotic quest to find the Fountain of Youth  in 16th-century Florida. Caparra was deemed unsuitable for a long-term  settlement, however, and the residents soon moved to an island a short  distance to the east, to the present site of Old San Juan. 

Rise to Importance  

The new city of San Juan Batista de Puerto Rico quickly became famous  for its good location and port, and it rose to importance in the  colonial administration. Alonso Manso, the first bishop to  arrive in the Americas, became bishop of Puerto Rico in 1511. San Juan  became the first ecclesiastical headquarters for the New World and  served as the first base for the Inquisition as well. By 1530, barely 20  years after its founding, the city supported a university, a hospital,  and a library. 

Piracy  

San Juan quickly came to the attention of Spain’s rivals in Europe. The  first attack on the island took place in 1528, when the French razed  several outlying settlements, leaving only San Juan intact. Spanish  troops started building San Felipe del Morro, a formidable castle, in  1539. Sir Francis Drake  and his men attacked the island in 1595 but were held off. In 1598,  however, George Clifford and his force of English privateers managed to  capture the island, remaining for several months before illness and  local resistance drove them away. That was the only time El Morro castle  was ever captured by an invading force. 

The 17th and 18th Centuries  

San Juan declined somewhat after its initial importance, as wealthier  cities such as Lima and Mexico City thrived under the colonial  administration. It continued to serve as a strategic military location  and port, however, and the island produced significant sugarcane and  ginger crops. It also became known for breeding fine horses, prized by  Spanish conquistadors campaigning on the mainland. Dutch pirates  attacked in 1625, capturing the city but not the fort. In 1797, a  British fleet of approximately 60 ships attempted to take San Juan but  failed in what is known on the island as “The Battle of San Juan.” 

Read more about the history of Old San Juan here