In 1508 Juan Ponce de León founded the original settlement, Caparra (named after the province Caceres, Spain, birthplace of the then-governor of Spain’s Caribbean territories, Nicolas de Ovando), today known as the Pueblo Viejo sector of Guaynabo, behind the almost land-locked harbor just to the west of the present San Juan metropolitan area. A year later, the settlement was abandoned and moved to a site which was called at the time Puerto Rico, a name that evoked that of a similar geographical feature in the island of Gran Canaria, Canary Islands, which meant “rich port” or “good port”. In 1521, the newer settlement was given its formal name of “San Juan Bautista de Puerto Rico”, following the usual custom of christening the town with both its formal name and the name which Christopher Columbus had originally given the island, honoring John the Baptist. The indistinct use of “San Juan Bautista” and “Puerto Rico” for calling both the city and the island led to a reversal in practical use by most inhabitants: by 1746 the name for the city (Puerto Rico) had become that of the entire island, while the name for the Island (San Juan Bautista) had become the name for the city.
In Spanish colonial times, most of the urban population resided in what is known now as Old San Juan. Old San Juan is located on the western half of a small island (the Isleta de San Juan) connected to the mainland by bridges and a causeway. The island, which comprises an area of 47 sq. mi./122 km²., also hosts the working class neighborhood of Puerta de Tierra, which is also the site of most of Puerto Rico’s central government buildings, including the commonwealth’s capitol.
The old city is the main cultural tourist attraction for Puerto Rico, and the bay side is lined by slips for large cruise ships. The core old city is characterized by its narrow cobblestone streets and colonial buildings, and encompasses less than a mile by a mile and a half.
The buildings in Old San Juan date back to the 16th and 17th century. Parts of the old city remain partly enclosed by massive walls and contains several defensive structures and notable forts, such as Fort San Felipe del Morro (begun 1539) and Fort San Cristóbal (17th century), both part of San Juan National Historic Site, and El Palacio de Santa Catalina, also known as La Fortaleza (begun in 1533), which serves as the governor’s mansion. Other buildings of interest predating the nineteenth century are the Ayuntamiento or Alcaldía (City Hall), the San José Church (1523) and the adjacent former Dominican monastery; and the former house of the Ponce de León family known as Casa Blanca.
San Juan was used by trade and military ships traveling from Spain as the first stop over in the Americas, making it an important settlement of the Spanish Empire. For this reason, it was also the target of the foreign powers of the time. The Spanish built a network of fortifications to protect the transportation of gold and silver from the New World to Europe.
The city saw attacks from the English in 1595 by Sir Francis Drake and 1598 led by George Clifford, Earl of Cumberland. The artillery from the fortification of El Morro repelled Drake, however Clifford managed to land troops and lay siege to the city. A few months into the British occupation, Clifford was forced to abandon his expedition when his troops began to suffer from exhaustion and sickness. Later, the city was sacked by the Dutch forces, lead by Boudewijn Hendricksz, in 1625, but Fort San Felipe del Morro withstood the assault and was never taken. The English returned in 1797, during the French Revolutionary Wars, led by Sir Ralph Abercromby, who had just conquered Trinidad. His army laid siege to the city but was forced to withdraw in defeat as the Puerto Rican defenses proved more resilient than those of Trinidad. Various events and circumstances, including liberalized commerce with Spain, opening of the island to immigrants, and the colonial revolutions, led to an expansion of the island and city in the late 18th and early 19th century.
In May 1898, United States Navy ships, among them the USS Detroit, USS Indiana, USS New York, USS Amphitrite, USS Terror and USS Montgomery, and commanded by Rear Admiral William T. Sampson, bombed the city during the Spanish-American War; although the city was not occupied. However, on July 25, General Nelson A. Miles, with 3,300 soldiers, landed at Guánica (in southwestern Puerto Rico) and took over the island with little resistance. Spain ceded the island to the United States later the same year by the signing of the Treaty of Paris.