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Founding

In 1508, Juan Ponce de León founded the original settlement which he called Caparra. It was named after a former Roman city in the province of Cáceres in Spain, the birthplace of Nicolás de Ovando, then the Governor of Spain's Caribbean territories. Today, it is part of the Pueblo Viejo district of Guaynabo, directly to the west of the modern municipality of San Juan. A year later, the settlement was moved to a site then called Puerto Rico, Spanish for "rich port" or "good port", after its similar geographical features to the town of Puerto Rico de Gran Canaria in the Canary Islands.

The local Catholic diocese, the second oldest in the Americas and the oldest in the United States, was founded in the newly built settlement on August 8 of 1511. In 1521, the newer settlement was given its formal name: Ciudad de Puerto Rico de San Juan Bautista. Many of the oldest European-founded institutions in the Western Hemisphere, such as the Santo Tomás de Aquino Convent and the Nuestra Señora de la Concepción Hospital, were established during this time in San Juan.

The ambiguous use of San Juan Bautista and Puerto Rico for both the city and the island in time 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, leading to the city being identified as Puerto Rico de Puerto Rico on maps of the era.