Although details are sketchy, Vieques is believed to have been inhabited by a series of indigenous peoples possibly thousands of years before Christopher Columbus “discovered” Puerto Rico in 1493. Based on the discovery of remains found in Vieques, some historians date the earliest inhabitants to the Stone Age era more than 3,500 years ago.

Thanks to a few archaeological digs in Vieques, slightly more is known about the Saladoids, believed to have come from Venezuela around 250 B.C. They were followed by the Ostionoids around 400 B.C. and eventually the Taínos, a highly developed society of agriculturalists who lived on both Vieques and Culebra. The Taínos ruled Puerto Rico from about A.D. 1200 until the Spanish colonists wiped them out in the 1500s.

In the early 1500s, two Taíno brothers in Vieques journeyed to mainland Puerto Rico to help their fellow natives fight the Spanish conquerors. As a result, the governor of Puerto Rico sent troops to Vieques, where all the Taínos were killed or enslaved. For a long time after that, the islands became lawless havens for pirates who sought refuge in the protected harbors and ambushed passing ships.

In 1832 a Frenchman named Le Guillou, known as the founder of Vieques, arrived on the island. Under Spanish authority, he restored order to the island and helped launch a golden era of prosperity. He brought over other Frenchmen from Guadeloupe and Martinique who established sugarcane plantations and processing plants that exported the products to Spain. The operations were manned by hundreds of slaves from Africa and thousands of free workers from surrounding islands.

In the early 1800s, the area around Esperanza was a thriving community with an opera house, a movie theater, and a cultural center. But as the town tried to expand to accommodate its growing population, difficulty in clearing the thick vegetation led leaders to relocate the town center to Isabel Segunda in 1844. Vieques continued to enjoy its prosperity until around 1880, when the sugar industry began to decline because of the development of cheaper sources elsewhere.

It was around this time that Culebra was being settled in fits and starts. The first attempt was in 1875 by a black Englishman named Stevens, who was named governor and given the task of protecting the island’s waters from pirates. Later that same year he was assassinated. He was followed in 1880 by a Spaniard, Cayetano Escudero Sanz, who established the first settlement, called San Ildefonso. The island’s sole economy was agriculture.

Upon the ratification in 1898 of the Treaty of Paris, which ended the Spanish-American War, Vieques and Culebra came under the rule of the U.S. government. During World War II, the U.S. military became the major landholder on both islands and began to use them for bomb practice and defense-testing sites. Protests begun in Culebra in 1971 led the United States to abandon operations in 1975. But Vieques toughed through 24 more years until a civilian was accidentally killed by a bomb in 1999. Several years of persistent protesting followed, which captured international attention and led to the incarceration of many activists. In 2003 the military abandoned its operations in Vieques. But its legacy lives on, some say, in the island’s extraordinarily high rate of cancer.