Pirates, freebooters, and buccaneers spent a great amount of their time on land partying and planning their next mission. Trips ashore allowed pirates to get off of their pitching, stinking ships, sell their stolen booty, and enjoy the fruits of their labors in local taverns. Some pirates, fresh from a profitable raid, took their money and invested in plantations and businesses. Others snuck back to their homes in England, France, or Spain. But most wasted their money in a few weeks and were soon back on the high seas looking for more loot.

Favorite Pirate Haunts

Buccaneers lived in dozens of towns and villages in the Americas. But their favorite haunts were the islands of Jamaica, Hispaniola, and the tiny isle of Tortuga. The pirates were easily spotted among the more law-abiding citizens of the Caribbean. They were often seen rampaging up...