Historically, the islands of Vieques and Culebra were included in maps and chronicles as part of the archipelago of the Virgin Islands, which was named Santa Úrsula y las Once Mil Vírgenes by Christopher Columbus after the legend of Saint Ursula and the 11,000 virgins.

Having been discovered during the second voyage of Columbus in 1493, the archipelago of the Virgin Islands was claimed by the Spanish Empire, but the Spaniards never settled them.

The inhabitants of Vieques, brothers of the Taínos of the Big Island of Puerto Rico, resisted the Spaniards' plans of colonization and slavery.

On September 19, 1898, the United States took possession of the islands after the signing of the armistice that ended military operations in the Spanish–American War.

In 1903 the U.S. government reserved all public lands belonging to the Spanish Crown on the island of Culebra for the use of the U.S. Navy.

At that time the U.S. military took complete control of the community of San Ildefonso de la Culebra, expelling its residents, and huddled in a small area of Bahía Sardinas, which they called Dewey in honor of an outstanding American admiral during the Spanish-American War.

On March 17, 1941, Public Law 13 was passed in Washington, allocating $35 million for the construction of the Vieques Base.

On August 25 of the same year, Public Law 247 allowed the U.S. Navy to take immediate possession of the lands to be expropriated in Vieques.

With the outbreak of World War II, Vieques Island became the main artillery- and bombing-practice area for the U.S. Navy and continued to be used for this purpose until 2003.