Guayanilla (Spanish pronunciation: [ɡwaʝaˈniʎa]) is a municipality of Puerto Rico located in southern coast of the island, bordering the Caribbean Sea, south of Adjuntas, east of Yauco; and west of Peñuelas and about 12 miles (19 km) west of Ponce. Guayanilla is spread over 16 wards and Guayanilla Pueblo (The downtown area and the administrative center of the city). It is part of the Yauco Metropolitan Statistical Area.

Guayanilla was founded by Puerto Rican criollos. The original name was Guadianilla in memory of a river of the same name in Spain. However, it was changed to Guayanilla to resemble a native word in the Taíno dialect. The name Guayanilla is derived from a combination of Guaynia and Santa Maria de Guadianilla.

The first Europeans settled in this area in 1511. In 1756, Yauco was founded as a town. Then Guayanilla was a borough of Yauco. Due to the very fertile lands and access to the local port where most of the local commerce occurred, Guayanilla became an important agricultural center, grew quickly, and was established as a separate municipality on February 27, 1833 by Governor Miguel de la Torre.

On April 27, 1584, Raleigh dispatched an expedition led by Philip Amadas and Arthur Barlowe to explore the Eastern coast of North America. They arrived on Roanoke Island on July 4, and soon established relations with the local natives, the Secotans and Croatoans. Barlowe returned to England with two Croatans named Manteo and Wanchese, who were able to describe the politics and geography of the area to Raleigh. Based on this information, Raleigh organized a second expedition, to be led by Sir Richard Grenville.

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