During the Golden Age of Piracy, Windward Islands played the important role in life and work of many pirate crews who preyed on merchant ships traveling on the outer reaches of Caribbean, often traveling to and from to Africa and Asia. The islands that are part of this grouping represents the biggest islands of Lesser Antilles, a small part of West Indies territories. They are all located south of the big group of Leeward Islands (from Puerto Rican Virgin Islands in the northwest all the way to the Dominica on the southeast) and cover everything from Dominica to Grenada. Alternatively, Windward Islands are all set between 12th and 16th northern parallel and 60th to 62nd western meridian longitude. Although very close, islands of Trinidad and Tobago are not part of Windward Islands.
The name Windward Islands was coined by the early visitors to the New World who noticed that prevailing West Indies trade winds that blew from west to east often put ships on the path somewhere between the Leeward Islands and the Windward Islands. This made the island of Dominica dividing line between two group of islands, enabling ship captains easier time to pick whether to sail toward the northern or southern set of islands. Several centuries later after first exploratory ships formed standard sail path toward the Caribbean, slave traders from Africa established a new way to approach the Central America seas. They arrived from the south, first encountering shores of the most southernmost Windward Islands like Grenada and Saint Vincent, continued toward the more crowded seas of Caribbean and eventually reaching their target of Central and North America.
The Windward Islands consist of over 90 islands of varying sizes, but the five largest ones are:
Dominica (not to be confused with the Dominican Republic on the isle of Hispaniola) – Largest of them all, discovered by Christopher Columbus. This island had a rich history of piracy because if was often a stop on travels of Spanish treasure fleets. One of the ship from such fleets sank near it in a storm, which fueled the myths of the secret treasure that was buried on small islands around Dominica by local (cannibal) natives.
Martinique – Small 436 square mile island that is today inhabited by less than 400 thousand inhabitants. During the Golden Age of Piracy, Martinique hosted one of the many Caribbean ports that were used for illegal trade. Near it shores famous Blackbeard managed to defeat two French military ships which were sent to capture him. Also, one of the most successful pirate captains of all time Bartholomew Roberts managed to evade authorities near Martinique. He showcased his displeasure toward Martinique by naming one of the skulls on his Jolly Rodger flag “A Martiniquian's Head”.
Saint Lucia – This small Island (283 square miles) entered history by being a base of French pirate François le Clerc in late 1550s, even before any other settlement was established on the island (this happened in 1643 after several failed attempts at settlement by both English and French).
Saint Vincent and the Grenadines – Small Windward Island that was often targeted by pirates, including the famous Blackbeard. Today, this islands closest connection to pirates are the beautiful scenic locations were several of the Pirates of the Caribbean movies were filmed.
Grenada – Seas around Grenada were hunting ground not only for the 17th-century pirates but also modern pirates who sometimes attack merchant and cruising ships between Grenada and Trinidad.