Hispaniola in the context of Buccaneer

Mesoamerica is a historical region and cultural area comprising the present day lands of central and southern Mexico, all of Belize, Guatemala, El Salvador, western Honduras, and the Greater Nicoya region of Nicaragua and Costa Rica. As a cultural area, Mesoamerica is defined by a mosaic of cultural traits developed and shared by its indigenous cultures.

In the pre-Columbian era, many indigenous societies flourished in Mesoamerica for more than 3,000 years before the Spanish colonization of the Americas began on Hispaniola in 1493. In world history, Mesoamerica was the site of two historical transformations: (i) primary urban generation, and (ii) the formation of New World cultures from the mixtures of the indigenous Mesoamerican peoples with the European, African, and Asian peoples who were introduced by the Spanish colonization of the Americas. Mesoamerica is one of the six areas in the world where ancient civilization arose independently (see cradle of civilization), and the second in the Americas, alongside the Caral–Supe in present-day Peru. Mesoamerica is also one of only five regions of the world where writing is known to have independently developed (the others being ancient Egypt, India, Sumer, and China).

The Spanish colonization of the Americas began in 1493 on the Caribbean island of Hispaniola (now Haiti and the Dominican Republic) after the initial 1492 voyage of Genoese mariner Christopher Columbus under license from Queen Isabella I of Castile. These overseas territories of the Spanish Empire were under the jurisdiction of Crown of Castile until the last territory was lost in 1898. Spaniards saw the dense populations of Indigenous peoples as an important economic resource and the territory claimed as potentially producing great wealth for individual Spaniards and the crown. Religion played an important role in the Spanish conquest and incorporation of indigenous peoples, bringing them into the Catholic Church peacefully or by force. The crown created civil and religious structures to administer the vast territory. Spanish men and women settled in greatest numbers where there were dense indigenous populations and the existence of valuable resources for extraction.

The Spanish Empire claimed jurisdiction over the New World in the Caribbean and North and South America, with the exception of Brazil, ceded to Portugal by the Treaty of Tordesillas. Other European powers, including England, France, and the Dutch Republic, took possession of territories initially claimed by Spain. Although the overseas territories under the jurisdiction of the Spanish crown are now commonly called "colonies" the term was not used until the second half of 18th century. The process of Spanish settlement, now called "colonization" and the "colonial era" are terms contested by scholars of Latin America and more generally.

New Spain, officially the Viceroyalty of New Spain (Spanish: Virreinato de Nueva España [birejˈnato ðe ˈnweβa esˈpaɲa] ; Nahuatl: Yankwik Kaxtillan Birreiyotl), originally the Kingdom of New Spain, was an integral territorial entity of the Spanish Empire, established by Habsburg Spain. It was one of several domains established during the Spanish conquest of the Americas, and had its capital in Mexico City. Its jurisdiction comprised a large area of the southern and western portions of North America, mainly what became Mexico and the Southwestern United States, but also California, Florida and Louisiana; Central America (as part of Mexico); the Caribbean like Hispaniola and Martinique, and northern parts of South America, even Colombia; several Pacific archipelagos, including the Philippines and Guam. Additional Asian colonies included "Spanish Formosa", on the island of Taiwan.

After the 1521 Spanish conquest of the Aztec Empire, conqueror Hernán Cortés named the territory New Spain, and established the new capital, Mexico City, on the site of Tenochtitlan, the capital of the Aztec Empire. Central Mexico became the base of expeditions of exploration and conquest, expanding the territory claimed by the Spanish Empire. With the political and economic importance of the conquest, the crown asserted direct control over the densely populated realm. The crown established New Spain as a viceroyalty in 1535, appointing as viceroy Antonio de Mendoza, an aristocrat loyal to the monarch rather than the conqueror Cortés. New Spain was the first of the viceroyalties that Spain created, the second being Peru in 1542, following the Spanish conquest of the Inca Empire. Both New Spain and Peru had dense indigenous populations at conquest as a source of labor and material wealth in the form of vast silver deposits, discovered and exploited beginning in the mid-1600s.

The Lucayan Archipelago, also known as the Bahamian Archipelago, is an island group comprising the sovereign nation of Bahamas and the British Overseas Territory of the Turks and Caicos Islands in the North Atlantic Ocean. The archipelago is in the Caribbean region, stretching from south-east of Florida in the mainland United States to northern Hispaniola. There are about 740 islands and 2,400 cays, of which only 38 are inhabited.

The geography of Puerto Rico encompasses the geographical features of Puerto Rico, a Caribbean archipelagic and island nation centered around a collective identity based on its land, history, ethnicity, culture, and language, and organized as a self-governing unincorporated territory of the United States. Located between the Greater and Lesser Antilles in the northeastern Caribbean Sea, east of Hispaniola, west of Saint Thomas, north of Venezuela, and south of the Puerto Rico Trench, it consists of the eponymous main island of Puerto Rico and 142 smaller islands, islets, and cays, including San Juan Islet in the north, Vieques and Culebra islands in the Virgin Islands, and Palominos island and Icacos cay in La Cordillera nature reserve in the east, Caja de Muertos island in Caja de Muertos reserve, and Caracoles and Media Luna cays in La Parguera reserve in the south, and Mona, Monito, and Desecheo islands in the Mona Passage in the west.

Measuring 177 km (110 mi; 96 nmi) in length and 65 km (40 mi; 35 nmi) in width with a land area of 8,868 sq km (3,424 sq mi), the main island of Puerto Rico is the 4th largest in the Caribbean, 29th in the Americas, and 81st in the world, making it the 170th largest country or dependency by surface area. With 3.2 million residents, it is also the 4th largest in the Caribbean, 4th in the Americas, and 31st in the world, making it the 136th largest country or dependency by population.

The Dominican Republic is a country in the Caribbean located on the island of Hispaniola in the Greater Antilles of the Caribbean Sea in the North Atlantic Ocean. It shares a maritime border with Puerto Rico to the east and a land border with Haiti to the west, occupying the eastern five-eighths of Hispaniola which, along with Saint Martin, is one of only two islands in the Caribbean shared by two sovereign states. In the Antilles, the country is the second-largest nation by area after Cuba at 48,671 square kilometers (18,792 sq mi) and second-largest by population after Haiti with approximately 11.4 million people in 2024, of whom 3.6 million reside in the metropolitan area of Santo Domingo, the capital city.

The native Taíno people had inhabited Hispaniola prior to European contact, dividing it into five chiefdoms. Christopher Columbus claimed the island for Castile, landing there on his first voyage in 1492. The colony of Santo Domingo became the site of the first permanent European settlement in the Americas. In 1697, Spain recognized French dominion over the western third of the island, which became the independent First Empire of Haiti in 1804. A group of Dominicans deposed the Spanish governor and declared independence from Spain in November 1821, but were annexed by Haiti in February 1822. Independence came 22 years later in 1844, after victory in the Dominican War of Independence. The next 72 years saw several civil wars, failed invasions by Haiti, and a brief return to Spanish colonial status, before permanently ousting the Spanish during the Dominican Restoration War of 1863–1865. From 1930, the dictatorship of Rafael Trujillo ruled until his assassination in 1961. Juan Bosch was elected president in 1962 but was deposed in a military coup in 1963. The Dominican Civil War of 1965 preceded the authoritarian rule of Joaquín Balaguer (1966–1978 and 1986–1996). Since 1978, the Dominican Republic has moved towards representative democracy.

The Greater Antilles is a grouping of the larger islands in the Caribbean Sea, including Cuba, Hispaniola, Puerto Rico, and Jamaica, together with Navassa Island and the Cayman Islands. Seven island states share the region of the Greater Antilles, with Haiti and the Dominican Republic sharing the island of Hispaniola. Together with the Lesser Antilles, they make up the Antilles, which along with the Lucayan Archipelago, form the West Indies in the Caribbean region of the Americas.

While most of the Greater Antilles consists of independent countries, Puerto Rico and Navassa Island are unincorporated territories of the United States, while the Cayman Islands are a British Overseas Territory. The largest island is Cuba, which extends to the western end of the island group. Puerto Rico lies on the eastern end, and the island of Hispaniola, the most populated island, is located in the middle. Jamaica lies to the south of Cuba, while the Cayman Islands are located to the west. The state of Florida is the closest point in the U.S. mainland to the Greater Antilles, while the Florida Keys, though not part of the Greater Antilles, is an island group north of Cuba.

Mona Island (Spanish: Isla de Mona) is the third-largest island of the Puerto Rican archipelago, after the main island of Puerto Rico and Vieques. It is the largest of three islands in the Mona Passage, the strait between Hispaniola and Puerto Rico, with the others being Monito Island and Desecheo Island. It measures about 7 miles by 4 miles (11 km by 7 km), and lies 41 mi (66 km) west of Puerto Rico, of which it is administratively a part. It is one of two islands that make up the Isla de Mona e Islote Monito barrio in the municipality of Mayagüez.

The island is managed under the Mona and Monito Islands Nature Reserve (Reserva Natural Islas de Mona y Monito). There are no permanent inhabitants; only rangers and biologists from the Puerto Rico Department of Natural and Environmental Resources reside on the island, to manage visitors and take part in research projects. The island, along with Monito, form part of the Mona and Monito Islands National Natural Landmark which recognizes and preserves the islands' ecosystem as an outstanding example of diversity and natural history. The island is home to a number of endemic species such as the Mona ground iguana and it is an important seabird area.

The Taíno were the Indigenous peoples of the Greater Antilles and surrounding islands. At the time of European contact in the late 15th century, they were the principal inhabitants of most of what is now The Bahamas, Cuba, the Dominican Republic, Haiti, Jamaica, Puerto Rico, and the northern Lesser Antilles. The Lucayan branch of the Taíno were the first New World people encountered by Christopher Columbus, in the Bahama Archipelago on October 12, 1492. The Taíno historically spoke an Arawakan language. Granberry and Vescelius (2004) recognized two varieties of the Taino language: "Classical Taino", spoken in Puerto Rico and most of Hispaniola, and "Ciboney Taino", spoken in the Bahamas, most of Cuba, western Hispaniola, and Jamaica. They lived in agricultural societies ruled by caciques with fixed settlements and a matrilineal system of kinship and inheritance. Taíno religion centered on the worship of zemis. The Taíno are sometimes also referred to as Island Arawaks or Antillean Arawaks. Indigenous people in the Greater Antilles did not refer to themselves originally as Taíno; the term was first explicitly used in this sense by Constantine Samuel Rafinesque in 1836.

Historically, anthropologists and historians believed that the Taíno were no longer extant centuries ago, or that they gradually merged into a common identity with African and Hispanic cultures. Scholarly attitudes to Taíno survival and resurgence began to change around the year 2000. Many people today identify as Taíno and many more have Taíno descent, most notably in Puerto Rico, Cuba, and Dominica. A substantial number of Puerto Ricans, Cubans, and Dominicans have Indigenous mitochondrial DNA, which may suggest Taíno descent through the direct female line, especially in Puerto Rico. While some communities describe an unbroken cultural heritage passed down through the generations, often in secret, others are revivalist communities who seek to incorporate Taíno culture into their lives.

Juan Ponce de León (c. 1474 – July 1521) was a Spanish explorer and conquistador known for leading the first official European expedition to Puerto Rico in 1508 and Florida in 1513. He was born in Santervás de Campos, Valladolid, Spain, in 1474. Though little is known about his family, he was of noble birth and served in the Spanish military from a young age. He first came to the Americas as a "gentleman volunteer" with Christopher Columbus's second expedition in 1493.

By the early 1500s, Ponce de León was a top military official in the colonial government of Hispaniola, where he helped crush a rebellion of the native Taíno people. He was authorized to explore the neighboring island of Puerto Rico in 1508 and to take office as the first Governor of Puerto Rico by appointment of the Spanish crown in 1509. While Ponce de León grew quite wealthy from his plantations and mines, he faced an ongoing legal conflict with Diego Colón, the late Christopher Columbus's son, over the right to govern Puerto Rico. After a long court battle, Colón replaced Ponce de León as governor in 1511. Ponce de León decided to follow the advice of the sympathetic King Ferdinand and explore more of the Caribbean Sea.

La Santa María de la Inmaculada Concepción (Spanish: [la ˈsãn̪.t̪a maˈɾi.a ð̞e̞ la ĩm.ma.kuˈla.ð̞a kõn̟.θeβ̞ˈθjõn] lit. 'The Holy Mary of the Immaculate Conception'), or La Santa María (Spanish: [la ˈsãn̪.t̪a maˈɾi.a]), originally La Gallega (Spanish: [la ɡaˈʝe.ɣ̞a]), was the largest of the three small ships used by Christopher Columbus in his first expedition across the Atlantic Ocean in 1492, with the backing of the Spanish monarchs. Her master and owner was Juan de la Cosa.

In 1492 the ship ran aground on a sand bar near modern day Cap-Haïtien of the island of Hispaniola. The wood of the ship was stripped and used to make a wooden fort at Limonade, and one anchor survives to the present day in a Museum in Haiti. In the 19th and 20th century several replicas have been made of varying nature, as the size and details of the original are unknown.

Most of the Caribbean countries are islands in the Caribbean Sea, with only a few in inland lakes. The largest islands include Cuba, Hispaniola, Jamaica and Puerto Rico. Some of the smallest islands are referred to as a rock or reef.

Islands are listed in alphabetical order by sovereign state. Islands with coordinates can be seen on the map linked to the right.

Haiti, officially the Republic of Haiti, is a country in the Caribbean on the island of Hispaniola in the Caribbean Sea, east of Cuba and Jamaica, and south of the Bahamas. It occupies the western three-eighths of the island, which it shares with the Dominican Republic. Haiti is the third largest country in the Caribbean, and with an estimated population of 11.4 million, is the most populous Caribbean country. The capital and largest city is Port-au-Prince.

Haiti was originally inhabited by the Taíno people. In 1492, Christopher Columbus established the first European settlement in the Americas, La Navidad, on its northeastern coast. The island was part of the Spanish Empire until 1697, when the western portion was ceded to France and became Saint-Domingue, dominated by sugarcane plantations worked by enslaved Africans. The 1791–1804 Haitian Revolution made Haiti the first sovereign state in the Caribbean, the second republic in the Americas, the first country in the Americas to officially abolish slavery, and the only country in history established by a slave revolt. The 19th century saw political instability, international isolation, debt to France, and failed invasions of the Dominican Republic, including a costly war. U.S. forces occupied Haiti from 1915 to 1934, followed by dictatorial rule of the Duvalier family (1957–1986). Following a coup d'état in 1991, a U.S.-led multinational force intervened in 1994; a second coup in 2004 was followed by a United Nations intervention. In the 2010s, a catastrophic earthquake and a large-scale cholera outbreak devastated the country.

Navassa Island (/nəˈvæsə/; Haitian Creole: Lanavaz; French: Île de la Navasse, sometimes la Navase) is an uninhabited island in the Windward Passage of the Caribbean Sea. Located east of Jamaica, south of Cuba, and 40 nautical miles (74 km; 46 mi) west of Jérémie on the Tiburon Peninsula of Haiti, it is subject to an ongoing territorial dispute between Haiti and the United States, the latter of which administers the island through the U.S. Fish and Wildlife Service.

The U.S. has claimed the island as an appurtenance since 1857, based on the Guano Islands Act of 1856. Haiti's claim over Navassa goes back to the Treaty of Ryswick in 1697 that recognized French, rather than Spanish, control of the western portion of the island of Hispaniola and other specifically named nearby islands. However, there was no mention of Navassa in the treaty detailing terms. Haiti's 1801 constitution claimed several nearby islands by name, among which Navassa was not listed, but also laid claim to "other adjacent islands", which Haiti maintains included Navassa. The U.S. claim to the island, first made in 1857, asserts that Navassa was not included among the unnamed "other adjacent islands" in the 1801 Haitian Constitution. Since the Haitian Constitution of 1874, Haiti has explicitly named "la Navase" as one of the territories it claims. It maintains that it has continuously been claimed as part of Haiti since 1801.

Jamaica is an island country in the Caribbean, covering 10,990 square kilometres (4,240 sq mi). It is the third-largest island in the Greater Antilles and the Caribbean, after Cuba and the island of Hispaniola. Jamaica lies about 145 km (78 nmi) south of Cuba, 191 km (103 nmi) west of Hispaniola (the island containing Haiti and the Dominican Republic), and 215 km (116 nmi) southeast of the Cayman Islands (a British Overseas Territory). With 2.8 million people, Jamaica is the third most populous Anglophone country in the Americas and the fourth most populous country in the Caribbean. Kingston is the country's capital and largest city.

The indigenous Taíno peoples of the island gradually came under Spanish rule after the arrival of Christopher Columbus in 1494. Many of the indigenous people either were killed or died of diseases, after which the Spanish brought large numbers of Africans to Jamaica as slaves. The island remained a possession of Spain, under the name Santiago, until 1655, when England (part of what would become the Kingdom of Great Britain) conquered it and named it Jamaica. It became an important part of the colonial British West Indies. Under Britain's colonial rule, Jamaica became a leading sugar exporter, with a plantation economy dependent on continued importation of African slaves and their descendants. The British fully emancipated all slaves in 1838, and many freedmen chose to have subsistence farms rather than to work on plantations. Beginning in the 1840s, the British began using Chinese and Indian indentured labourers for plantation work. Jamaicans achieved independence from the United Kingdom on 6 August 1962.

The Treaty of Tordesillas, signed in Tordesillas, Spain, on 7 June 1494, and ratified in Setúbal, Portugal, divided the newly discovered lands outside Europe between the Kingdom of Portugal and the Crown of Castile, along a meridian 370 leagues or 2,100 kilometres (1,300 mi) west of the Cape Verde islands, off the west coast of Africa. That line of demarcation was about halfway between Cape Verde (already Portuguese) and the islands visited by Christopher Columbus on his first voyage (claimed for Castile and León), named in the treaty as Cipangu and Antillia (Cuba and Hispaniola).

The lands to the east would belong to Portugal and the lands to the west to Castile, modifying an earlier bull by Pope Alexander VI. The treaty was created on 7 June 1494, then ratified by Spain on 2 July 1494, by Portugal on 5 September 1494, and by Pope Julius II on 24 January 1506. The other side of the world was divided a few decades later by the Treaty of Zaragoza, signed on 22 April 1529, which specified the antimeridian to the line of demarcation specified in the Treaty of Tordesillas. Portugal and Spain largely respected the treaties, while the Indigenous peoples of the Americas did not acknowledge them.

The Spanish West Indies, Spanish Caribbean or the Spanish Antilles (also known as "Las Antillas Occidentales" or simply "Las Antillas Españolas" in Spanish) were Spanish territories in the Caribbean. In terms of governance of the Spanish Empire, The Indies was the designation for all its overseas territories and was overseen by the Council of the Indies, founded in 1524 and based in Spain. When the Crown established the Viceroyalty of New Spain in 1535, the islands of the Caribbean came under its jurisdiction.

The islands ruled by Spain were chiefly the Greater Antilles: Hispaniola (including modern-day Haiti and the Dominican Republic), Cuba, Jamaica, and Puerto Rico. The majority of the Taíno, the indigenous populations on these islands, had died out or had mixed with the European colonizers by 1520. Spain also claimed the Lesser Antilles including Martinica, but these smaller islands remained largely independent until they were seized or ceded to other European powers as a result of war, or diplomatic agreements during the 17th and 18th centuries.