The Spanish conquistadors of the New World thought in terms of urban landscapes and municipal organization.
They did not launch their conquista de las Indias from ocean-going caravels or itinerant campsites.
The Spanish needed solid dwellings, preferably surrounded by rock walls, as they had in Europe.
 Juan Ponce de León spent days searching for the best place to build a villa, the blueprint for a colonial city.
Santo Domingo governor Nicolás de Ovando had appointed him to pacify and evangelize the nearby island, which Christopher Columbus had named "San Juan Bautista" during his second voyage to the Americas.
A frontier with dreaded, reportedly-cannibalistic Caribs on its coast, it was an opportunity to demonstrate machismo and glorify God and country.
Following de Ovando's recommendation, Ferdinand II of Aragon made Ponce de León an adelantado and authorized him to conquer the Taíno island.
Boriquén, the indigenous name for Puerto Rico, would be the second Caribbean island to become part of the Spanish Empire.

In 1508 Ponce de León sailed into the Bay of Guanica, on the west of the island, where local cacique Agüeybaná I welcomed his men as allies against the Caribs.
However, the Spanish did not find a suitable place to settle there.
The adelantado and his small team of hidalgos traversed the island until they saw a spacious, almost-landlocked bay on the northeastern shore.
No indigenous peoples seemed to claim the area, since it was subject to Carib raids.
Ponce de León named the body of water the Bay of the Wealthy Port (Spanish: Bahía de Puerto Rico).

Ponce de León pushed inland and ordered the first Spanish settlement on the island, 3 miles (4.8 km) from the bay.
Following de Ovando's suggestion, he named the settlement Caparra.
The explorer chose the site because of its proximity to the sea and "to the gold mines and farms of the Toa Valley".

Caparra proved to be an inauspicious venture.
Mendicant friars appealed to Ponce de León to move the settlement closer to the bay (and its sea breezes), saying that its present location was lethal to children.
The governor was adamantly opposed, since he had had a house built in Caparra.
In 1511 the crown appointed a new governor, Juan Cerón, who received royal permission to relocate the village.
According to Rodrigo de Figueroa's map, the villagers resettled on a three-mile blustery, wooded islet at the bay's entrance.
In 1521, the residents completed the resettlement and named the new village "Villa de Puerto Rico".
Several years later, after a royal upgrade, the settlement was renamed "Ciudad de Puerto Rico".
Colonial engineers fortified the islet with walls and castles, connecting it to mainland Puerto Rico with the San Antonio Bridge, and it came to be known as "the walled city".

Sixteenth-century Spanish historian and indigenous activist Bartolomé de las Casas described the bay and its surrounding area names different from those presently used: La isla que llamamos de San Juan, que por vocablo de la lengua de los indios, vecinos naturales della, se nombraba Boriquén ... tiene algunos puertos no buenos, si no es el que llaman Puerto-Rico ("That island we call San Juan, which according to the native Indian language was called Boriquén, has but a few inferior harbors, except the one called Puerto-Rico").
According to de las Casas, the Indians called their island "Boriquén"; the Spanish called it "San Juan", and its harbor "Puerto Rico".
Over time, the island became Puerto Rico and its harbor (and bay) San Juan; the Indian name changed to Borinquen, with no diacritic and an extra n.
The Spanish conquistadors of the New World thought in terms of urban landscapes and municipal organization. They did not launch their conquista de las Indias from ocean-going caravels or itinerant campsites. The Spanish needed solid dwellings, preferably surrounded by rock walls, as they had in Europe.  Juan Ponce de León spent days searching for the best place to build a villa, the blueprint for a colonial city. Santo Domingo governor Nicolás de Ovando had appointed him to pacify and evangelize the nearby island, which Christopher Columbus had named "San Juan Bautista" during his second voyage to the Americas. A frontier with dreaded, reportedly-cannibalistic Caribs on its coast, it was an opportunity to demonstrate machismo and glorify God and country. Following de Ovando's recommendation, Ferdinand II of Aragon made Ponce de León an adelantado and authorized him to conquer the Taíno island. Boriquén, the indigenous name for Puerto Rico, would be the second Caribbean island to become part of the Spanish Empire.
In 1508 Ponce de León sailed into the Bay of Guanica, on the west of the island, where local cacique Agüeybaná I welcomed his men as allies against the Caribs. However, the Spanish did not find a suitable place to settle there. The adelantado and his small team of hidalgos traversed the island until they saw a spacious, almost-landlocked bay on the northeastern shore. No indigenous peoples seemed to claim the area, since it was subject to Carib raids. Ponce de León named the body of water the Bay of the Wealthy Port (Spanish: Bahía de Puerto Rico).
Ponce de León pushed inland and ordered the first Spanish settlement on the island, 3 miles (4.8 km) from the bay. Following de Ovando's suggestion, he named the settlement Caparra. The explorer chose the site because of its proximity to the sea and "to the gold mines and farms of the Toa Valley".
Caparra proved to be an inauspicious venture. Mendicant friars appealed to Ponce de León to move the settlement closer to the bay (and its sea breezes), saying that its present location was lethal to children. The governor was adamantly opposed, since he had had a house built in Caparra. In 1511 the crown appointed a new governor, Juan Cerón, who received royal permission to relocate the village. According to Rodrigo de Figueroa's map, the villagers resettled on a three-mile blustery, wooded islet at the bay's entrance. In 1521, the residents completed the resettlement and named the new village "Villa de Puerto Rico". Several years later, after a royal upgrade, the settlement was renamed "Ciudad de Puerto Rico". Colonial engineers fortified the islet with walls and castles, connecting it to mainland Puerto Rico with the San Antonio Bridge, and it came to be known as "the walled city".
Sixteenth-century Spanish historian and indigenous activist Bartolomé de las Casas described the bay and its surrounding area names different from those presently used: La isla que llamamos de San Juan, que por vocablo de la lengua de los indios, vecinos naturales della, se nombraba Boriquén ... tiene algunos puertos no buenos, si no es el que llaman Puerto-Rico ("That island we call San Juan, which according to the native Indian language was called Boriquén, has but a few inferior harbors, except the one called Puerto-Rico"). According to de las Casas, the Indians called their island "Boriquén"; the Spanish called it "San Juan", and its harbor "Puerto Rico". Over time, the island became Puerto Rico and its harbor (and bay) San Juan; the Indian name changed to Borinquen, with no diacritic and an extra n.
San Juan Bay