Piracy in 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.

Pirates were often former sailors experienced in naval warfare. In the 16th century, pirate captains recruited seamen to loot European merchant ships, especially the Spanish treasure fleets sailing from the Caribbean to Europe. The following quote by an 18th-century Welsh captain shows the motivations for piracy:

In an honest Service, there is thin Commons, low Wages, and hard Labour; in this, Plenty and Satiety, Pleasure and Ease, Liberty and Power; and who would not balance Creditor on this Side, when all the Hazard that is run for it, at worst, is only a sower Look or two at choaking. No, a merry Life and a short one shall be my Motto.

—Pirate Captain Bartholomew Roberts

Piracy was sometimes given legal status by the colonial powers, especially France under King Francis I (r. 1515–1547), in the hope of weakening Spain and Portugal's mare clausum trade monopolies in the Atlantic and Indian Oceans. This officially sanctioned piracy was known as privateering. From 1520 to 1560, French privateers were alone in their fight against the Crown of Spain and the vast commerce of the Spanish Empire in the New World. The French privateers were not considered pirates in France as they were in the service of the king of France, they were considered combatants and granted a lettre de marque or lettre de course which legitimized any actions they took under the French justice system. They were later joined by the English and Dutch. The English were dubbed "sea dogs".

The Caribbean had become an important center of European trade and colonization after Columbus' discovery of the New World for Spain in 1492. In the 1494 Treaty of Tordesillas the non-European world had been divided between the Spanish and the Portuguese along a north–south line 370 leagues west of the Cape Verde Islands. This gave Spain control of the Americas, a position the Spaniards later reiterated with an equally unenforceable papal bull (The Inter caetera). On the Spanish Main, the key early settlements were Cartagena in present-day Colombia, Porto Bello and Panama City on the Isthmus of Panama, Santiago on the southeastern coast of Cuba, and Santo Domingo on the island of Hispaniola. In the 16th century, the Spanish were mining extremely large quantities of silver from the mines of Zacatecas in New Spain (Mexico) and Potosí in Bolivia (formerly known as Upper Peru). The huge Spanish silver shipments from the New World to the Old attracted pirates and French privateers like François Leclerc or Jean Fleury, both in the Caribbean and across the Atlantic, all along the route from the Caribbean to Seville.

To combat this constant danger, in the 1560s the Spanish adopted a convoy system. A treasure fleet or flota would sail annually from Seville (and later from Cádiz) in Spain, carrying passengers, troops, and European manufactured goods to the Spanish colonies of the New World. This cargo, though profitable, was really just a form of ballast for the fleet as its true purpose was to transport the year's worth of silver to Europe. The first stage in the journey was the transport of all that silver from the mines in Bolivia and New Spain in a mule convoy called the Silver Train to a major Spanish port, usually on the Isthmus of Panama or Veracruz in New Spain. The flota would meet up with the Silver Train, offload its cargo of manufactured goods to waiting colonial merchants and then load its holds with the precious cargo of gold and silver, in bullion or coin form. This made the returning Spanish treasure fleet a tempting target, although pirates were more likely to shadow the fleet to attack stragglers than to engage the well-armed main vessels. The classic route for the treasure fleet in the Caribbean was through the Lesser Antilles to the ports along the Spanish Main on the coast of Central America and New Spain, then northwards into the Yucatán Channel to catch the westerly winds back to Europe.

By the 1560s, the Dutch United Provinces of the Netherlands and England, both Protestant states, were defiantly opposed to Catholic Spain, the greatest power of Christendom in the 16th century; while the French government was seeking to expand its colonial holdings in the New World now that Spain had proven they could be extremely profitable. It was the French who had established the first non-Spanish settlement in the Caribbean when they had founded Fort Caroline near what is now Jacksonville, Florida in 1564, although the settlement was soon wiped out by a Spanish attack from the larger colony of Saint Augustine. As the Treaty of Tordesillas had proven unenforceable, a new concept of "lines of amity", with the northern bound being the Tropic of Cancer and the eastern bound the Prime Meridian passing through the Canary Islands, is said to have been verbally agreed upon by French and Spanish negotiators of the Peace of Cateau-Cambrésis. South and west of these lines, respectively, no protection could be offered to non-Spanish ships, "no peace beyond the line." English, Dutch and French pirates and settlers moved into this region even in times of nominal peace with the Spanish.