1492 - 1493
Christopher Columbus leads his first voyage to the Indies, intending to reach Japan by a Western route.
1493 - 1496
Columbus' second voyage reaches the Leeward Islands, Jamaica, Puerto Rico and Hispaniola.
1493
Columbus brings sugar cane to the Americas, where it grows easily. This marks the foundation of the sugar industries in Jamaica, Haiti and Cuba.
1496
A Spanish colony is established at Santo Domingo in Hispaniola.
1498 - 1500
Columbus' third voyage reaches contemporary Trinidad, Tobago, Venezuela and Hispaniola.
1502 - 1504
Columbus' fourth voyage reaches contemporary Puerto Rico, Hispaniola, Cuba, Nicaragua, Costa Rica and Panama.
1509
A Spanish colony is established on Jamaica.
1511
Spanish colonisers establish coffee, sugar and tobacco plantations on Cuba.
1513
Juan Ponce de Leon sails from Puerto Rico and is the first European to reach the Gulf Stream.
1531
The Spanish cultivate tobacco in San Domingo.
1552
Bartolomé de las Casas' Short Account of the Destruction of the Indies is published.
1555 - 1563
John Hawkins enslaves people in the place we now know as Sierra Leone and transports them to the Caribbean.
1567 - 1573
Francis Drake embarks upon a series of voyages to the West Indies, intended to disrupt and capture Spanish shipping.
1579
Francis Drake captures a Spanish treasure ship carrying 26 tons of silver and 80 lbs of gold.
1585 - 1604
Anglo-Spanish War breaks out following the capture of English merchant ships in Spanish harbours. Though much of the conflict took place in Europe, England launched repeated expeditions against Spanish territories in the New World.
1585
Ginger grown in Jamaica is imported into Europe.
1592
Spanish colonists establish a colony on Trinidad.
1605
An English colony is established on the island of St Lucia. The indigenous Kalinago resist the colonisation and drive off the colonists.
1607
England establishes a colony in Virginia. Due to prevailing trade winds, the Caribbean becomes an important stopping point for ships sailing to the new colony.
1609
A flotilla travelling to Jamestown is struck by a storm. One ship is stranded at Bermuda, perhaps inspiring William Shakespeare's The Tempest. Its passengers establish a colony on the island before sailing on to Jamestown.
1609
British colonists attempt to colonise Grenada. They are driven off the island by the indigenous Kalinago.
1612
Bermuda is incorporated into the charter of the Virginia Company. A permanent colony is established at St George.
1615
First record of Dutch colony on Tortola.
1615
Operation of the colony at Bermuda is passed to the Somers Isles Company.
1616
Essequibo is colonised by Dutch traders.
1620
A colonial parliament, the House of Assembly, is created to govern the colony at Bermuda.
1624
An English colony is established on the island of St Christopher (St Kitts).
1625
Spanish forces sack the Dutch colony on Tortola.
1625
A French colony is established on St Kitts.
1625
English and French colonists from St Kitts establish a colony on Tortuga, off the coast of Hispaniola.
1625
English and Dutch colonists establish colonies on St Croix. Disputes between the colonies lead the Dutch colonists to abandon the island.
1626
A joint force of British and French colonists on St Kitts massacre a significant number of the indigenous Kalinago.
1627
Henry Powell lands on Barbados with a party of 80 colonists and 10 enslaved people to establish a colony.
1627
Berbice is colonised by the Dutch West India Company.
1628
Colonists from St Kitts establish a colony on Nevis.
1628
Dutch colonists attempt to establish a colony on Tobago, but are driven off by the Indigenous population and attacks by Kalinago from Grenada and St Vincent.
1629
An English colony is established on Providence Island.
1629
The English and French colonies on St Kitts and Nevis are destroyed by Spanish forces. The colonies return following the Spanish departure in 1630.
1629 - 1630
The French and English colonies on Tortuga are sacked by Spanish forces.
1631
The English colony on St Croix is sacked by Spanish forces.
1631
English and French colonists make a second attempt to establish colonies on Tortuga. The island becomes an important base for buccaneers.
1632
Colonists from St Kitts establish a colony on Antigua.
1632
Predominantly Irish colonists from St Kitts establish a colony on Montserrat.
1634
Dutch forces occupy the Spanish colony of Curaçao.
1635
A French colony is established on Martinique.
1635
A French colony is established on Guadeloupe.
1635
A Spanish attack on the English colony on Providence Island is repelled.
1635
Spanish forces sack the English and French colonies on Tortuga.
1636
A Dutch colony is established on St Eustatius. The island changes hands some 21 times between the 17th and 19th centuries.
1636
The legal basis for slavery is established by statute in Barbados.
1637
English colonists attempt to establish a colony on Tobago, but are ousted by the indigenous population.
1638
Spanish forces occupy Tortuga.
1638
English colonists make a second attempt to colonise St Lucia. This colony is again repulsed by Kalinago.
1639
A locally elected House of Assembly is formed in Barbados.
1641
The colony on Providence Island is sacked by Spanish forces.
1641
English slave traders begin importing enslaved people to Barbados.
1641
French forces take possession of Tortuga.
1642 - 1651
English Civil War.
1642
The first sustained European colony on Tobago is established by Courlanders from modern-day Latvia.
1645
English colonists return to St Croix.
1648
English colonists from Bermuda establish a colony in the Bahamas, on the island of Eleuthera.
1648
A French colony is established at Saint-Barthélemy.
1649
A French colony is established at Grenada.
1649
Enslaved people on two plantations on Barbados rise against the slaveholders over the lack of food.
1650
Spanish forces sack the English colony on St Croix. The island passes to French control and is subsequently ceded to the Knights of Malta.
1650
An English colony is established in Suriname.
1650
Colonists from St Kitts establish a colony on Anguilla.
1650
As Barbados is controlled by Royalists, Parliament issues an act halting all trade with the island.
1651
The Navigation Acts restricted the use of foreign ships in trade between Britain and her colonies.
1651 - 1666
Saint-Barthélemy is administered by the Knights of Malta.
1652
Barbados, held by Royalist forces, is captured by the Parliamentarian commander, George Ayscue.
1652 - 1654
First Anglo-Dutch War breaks out as England attempts to prevent Dutch trade in English colonies.
1654 - 1660
Anglo-Spanish War. Though the war ends with the restoration of Charles II in 1660, the conflict in the Caribbean continues until the 1667 Treaty of Madrid.
1654
Spanish forces occupy Tortuga for the final time.
1654
The Western Design, an English expedition against the Spanish West Indies, is launched with the objective of capturing Hispaniola.
1655
An English attack on Hispaniola is repulsed. The English forces instead turn to Jamaica, capturing the island.
1655
Groups of enslaved people escaping from plantations in Jamaica establish settlements in the Blue Mountains and in Cockpit Country. These groups come to be called 'Maroons'.
1659
The Dutch take control of Tobago.
1660
Restoration of Charles II.
1660
France and England agree not to colonise Dominica and St Vincent, islands occupied by Kalinago.
1660
French colonists agree a treaty with the Indigenous peoples of St Lucia, allowing the French to establish a colony on the island.
1660
A second Navigation Act is passed to promote English commerce and protect it from European competition in colonial trade.
1660
The Royal African Company is founded and is given a monopoly over the British slave trade.