Sail the Caribbean in search of fame and fortune
For a map of the Caribbean visit Shawn Brown's website. Jamaica, Tortuga and Hispaniola are all marked. Laguna de Terminos would be in the top left corner, just about where the arrow says "To Vera Cruz".
Hispaniola is the name for the large island which is now divided between Haiti and the Dominican Republic. The early buccaneers went there to hunt wild cattle for "boucan" (smoked or dried beef) and that's where the name comes from (because they were "boucaniers"). In Pirates you can sail to Hispaniola to gather provisions. If you hang around for long the Spanish will turn up and try to chase you away.
Laguna de Terminos
In the early years of the buccaneers there was a thriving trade (but illegal) logging trade on the coast of Belize, Honduras and Yucatan, and Laguna de Terminos was one of the major sources of logwood. In Pirates you can sail to Laguna de Terminos to cut logwood for cargo. If you hang around for long the Spanish will turn up and try to chase you away.
The voyage across the Altantic is a long and dangerous one, especially for smaller vessels, but goods from the new World fetch higher prices in Plymouth than in the Caribbean, so the trip might well be worthwhile. Espeically with a bigger ship and a big cargo.
In the time of the buccaneers Port Royal was the major base in Jamaica, the largest and most important of the Caribbean islands not controlled by Spain. It was famous for all the things you'd expect of a port full of pirates and described as the "richest and wickedest city in the world". In Pirates it's safe to use Port Royal if you're a merchant or a privateer, but it's very risky for a pirate.
The Azores are a group of Portugese-held islands in the Atlantic Ocean. On a modern map they seem very close to Europe but they're actually slap-bang in the middle of the most sensible route if you want to sail to the Caribbean (if you go via the Azores you get reasonably reliable winds: the crossing further north is less reliable and much more dangerous. And colder.
Throughout the period the buccaneers maintained a base on the island of Tortuga. It was often attacked by Spanish expeditions, but even when their attacks were successful it would soon be returned to former ways. There are no customers men in Tortuga, and if you're a pirate you'll need Tortuga as a base.