When the European merchant vessels sailed out to trade with India, less they knew about the unexplored world. They assumed that entire southeast Asia is part of a gigantic India, hence named it as Farther India while the islands that consist of today's Indonesia, Singapore, Malaysia, Brunei and Timor-Leste, became East Indies. A similar logic may have been applied to the Caribbean islands, hence the name West Indies. It's interesting to know that neither of the two Indies had anything to do with India, although both have considerable influence of India in them. The tiny islands of Trinidad and Jamaica were once settled with Indian migrants shipped from British India back in the 19th century, as labourers to European sugar farms. It's strange that to date the names have been stuck to it, the best example to prove this would be the explanation of the West Indies Federation - a short-lived political entity combining all the islands of the Caribbean which were once dependent on the United Kingdom. The federation existed between 1958 to 1962, having its capitals at Chaguaramas (in Trinidad) and Port of Spain (in Trinidad).
But these names weren't the original ones. Explorers from the kingdoms of Spain, France, Portugal and Great Britain sailed to these islands since the beginning of the 15th century and named them either after their rulers, or a religious figure, or how they described the local indigenous people living there. Certain names have been prominent all throughout the ages - Cuba, Jamaica being the two of them, while the term Hispaniola (also spelt as Spaniola) was used to denote the entire island made up of the Dominican Republic and Haiti. Another interesting thing to note here is that both Dominica and Dominican Republic share the same etymology, but are separated by various islands.
Today, none of the islands carries their indigenous names, lost all due to colonisation. But as the Europeans had arrived in the Caribbean, tribes such as Arawak, Kalinago, Taino and Galibi were the inhabitants that called their islands by totally different names. European explorers changed the entire pronunciation and christened European names that are in use today. Here's a list of all the islands of the Caribbean with their European names in italics while the indigenous names in bold dark red. The years in brackets are the first contact of Europeans to these islands.
- Cuba - Juana de Cuba / Fernandina (1492) Cobao
- Jamaica - San Iago (1494) Yamaye / Hamaica
- Bahamas :
- Watling Island - San Salvador (1492)
- Ragged Islands - Islas de Arena (1492)
- Rum Cay - Santa MarÃa de la Concepción (1492)
- Crooked Island - Isabela (1492)
- Grand Bahama - Islas Lucayos (1513)
- Grand Abaco - Lucayoneque (1565)
- Eleuthra - Eleutheriah (1647)
- Turks and Caicos Islands (UK) (1492)
- Haiti - Île de la Tortue et Côte de Saint-Domingue (1664)*
- Dominican Republic - Santo Domingo (1496)**
- Puerto Rico (USA) - Isla de San Juan Bautista / Porto Rico (1493) Borikén / Borinquen
- Virgin Islands (UK) - Las Islas Once Mil Virgenes (1493)
- St. Croix (part of Virgin Islands, USA) - Isla de Santa Cruz (1493) Ay Ay
- Anguilla - Isla de Anguila (1500) Malliouhana
- St. Kitts and Nevis - Isla de San Jorge / Saint-Christophe / Isla San Martin (1493) Liamuiga & Oualie
- Saint Martin (Fr.) - Isla San Martin (1493) Soualiga / Oualichi
- St. Barthelemy (Fr.) - Isla de San Bartolomeo (1493) Ouanalao
- Antigua and Barbuda - Isla Santa MarÃa de La Antigua / Antego / Antegoa / Antigoa (1493) Waladli & Wa'omoni
- Guadeloupe (Fr.) - Isla de Santa MarÃa de Guadalupe de Extremadura (1493) Karukera / Kalaoucera
- Dominica - Isla Dominga / Dominoco (1493) Wai'tukubuli
- Martinique (Fr.) - Isla Martinica / Martinico / Mittalanea (1502) Jouanacaeira / Madinina
- Montserrat (UK.) - Isla de Santa MarÃa de Montserrate (1493) Alliouagana
- St. Lucia - Isla de Santa Lucia / Sainte-Lucie (1502) Hewanorra / Iyanola
- St. Vincent & the Grenadines - Isla de San Vicente / Saint-Vincent (1498) Hairouna & Becouya / Kayryouacou / Cannouan
- Barbados - Isla de los Barbados / Ilha Barbados / Isla de Beruados / Barbadoes (1500) Ichirouganaim (pronounced as Ichi-rougan-aim)
- Grenada - Isla de Concepción (1498) Camerhogne
- Trinidad & Tobago - Isla La Santissima Trinidad (1498) Kairi / Iere
- Netherlands Antilles :
- Bonaire - Isla de Palo Brasil (1499)
- Curacao - Isla de los Gigantes / Captaincy of Curaçao (1499)
- Aruba (Neth.) - Oro Hubo (1502)
- Sint Eustatius (Neth.) - Isla de Santa Anastasia (1493) Aloi
- Sint Maarten (Neth.) - Isla San Martin / Soualiga (1493)
- Bermuda (UK) - La Bermuda (1503)
- Learie Constantine (Diego Martin, Trinidad & Tobago)
- Sir Isaac Vivian Alexander Richards (St. John's, Antigua & Barbuda)
- Brian Lara (Santa Cruz, Trinidad & Tobago)
- Courtney Walsh (Kingston, Jamaica)
- Shivnarine Chanderpaul (Unity Village, Guyana)***
- Daren Julius Garvey Sammy (Micoud, St. Lucia)
- Chris Gayle (Kingston, Jamaica)
- Dwayne John Bravo (Santa Cruz, Trinidad & Tobago)
- Denesh Ramdin (Couva, Trinidad & Tobago)
- Ramnaresh Ronnie Sarwan (Wakenaam Island, Guyana)***
- Carl Hooper (Georgetown, Guyana)***
- Daren Ganga (Barrackpore, Trinidad & Tobago)
- Jason Omar Holder (Bridgetown, Barbados) etc.

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