Roberto Cofresí, one of the last Caribbean pirates, was apprehended after his flagship sloop Anne was captured by authorities.

Roberto Cofresí y Ramírez de Arellano, better known as El Pirata Cofresí, was a Puerto Rican pirate. He was born into a noble family, but the political and economic difficulties faced by the island as a colony of the Spanish Empire during the regional independence wars against the metropole meant that his household was poor. Cofresí worked at sea from an early age which familiarized him with the region's geography, but it provided only a modest salary, and he eventually decided to abandon the sailor's life and became a pirate. He had previous links to land-based criminal activities, but the reason for Cofresí's change of vocation is unknown; historians speculate that he may have worked as a privateer aboard El Scipión, a ship owned by one of his cousins.

The Piracy of the Caribbean refers to the historical period of widespread piracy that occurred in the Caribbean Sea. Primarily between the 1650s and 1730s, where pirates frequently attacked and robbed merchant ships sailing through the region, often using bases or islands like Port Royal. The era of piracy in the Caribbean began in the 1500s and phased out in the 1830s after the navies of the nations of Western Europe and North America with colonies in the Caribbean began hunting and prosecuting pirates. The period during which pirates were most successful was from the 1650s to the 1730s. Piracy flourished in the Caribbean because of the existence of pirate seaports such as Fort Saint Louis in Martinique, Port Royal in Jamaica, Castillo de la Real Fuerza in Cuba, Tortuga in Haiti, and Nassau in the Bahamas. Piracy in the Caribbean was part of a larger historical phenomenon of piracy, as it existed close to major trade and exploration routes in almost all the five oceans.

In modern usage, a sloop is a sailboat with a single mast generally having only one headsail in front of the mast and one mainsail abaft (behind) the mast. It is a type of fore-and-aft rig. The mainsail may be of any type, most often Bermuda rig, but also others, such as gaff or gunter.