It's no secret that pirates enjoyed carousing during their precious time ashore at any number of pirate havens including Port Royal, Tortuga Island, New Providence, and Madagascar (see Chapter 16). Their riotous behavior while imbibing in various on-land exploits is part of what has earned them their wild reputation over the centuries. Pirates worked hard and played hard, and the mere thought of setting two feet on solid ground with their pockets heavy with coin sent most pirates into a feeding frenzy.

Pirates didn't often save their riches, instead choosing to splurge on food, excessive drink, and prostitutes — luxuries that were obviously lacking aboard a pirate ship. More often than not, what ensued on-land was rampant drunkenness, whoring, gambling, fighting, and even the occasional duel, and there were plenty of career gamblers, tavern owners, and whores who were happy to exploit pirates primed for debauchery. Unfortunately for most pirates, once their hard-earned money was spent on what most God-fearing people would consider evil deeds, they would be forced to once again take to the seas in search of plunder.

Eat, Drink, and Be Merry

As described in Chapter 9, pirate cuisine while onboard ship was something only a starving individual could possibly desire. When a pirate ship put to shore, proper food was a high priority, especially anything that was insect-free with nary a maggot in sight. Given that pirates were typically desperate for a hot meal, they were often happy with whatever food, or belly timber, a tavern or inn might be serving at the time. After months of drinking fetid water aboard ship, pirates were primed for proper drink, and this included wine, beer, and liquors such as rum and gin served in tankards. The oft-heard term grog typically refers to alcohol, usually rum or watered-down rum. The modern-day act of feeling groggy finds its origins in pirate vernacular, especially in regard to the morning after a night of drinking.

In the Caribbean during the seventeenth and eighteenth centuries, a popular concoction was Bumboo, or Bombo, a sweet and potent mixture of water, nutmeg, sugar, and rum that was favored by many sailors given that it was much tastier than the grog provided by the British Navy. Another pirate favorite was rumfustian, which featured sugar, beer, gin, sherry, and raw eggs blended together and served hot.

The pirate haven of Port Royal was known for a particularly lethal rum punch appropriately called kill-devil. Yet another mind-bender was flip, a hot mixture of a small or light beer combined with sugar and brandy. With all of these drinks at a pirate's disposal, it would seem appropriate that after long drinking binges a pirate would have a bad taste in his mouth. This unfortunate by-product of drunkenness was aptly described as “the cat has kittened in my mouth.”

Girl Crazy

Most pirate havens were swarming with prostitutes who were more than happy to take money from pirates and sailors who'd spent months at sea with nary a wench in sight. The act of catting, or pursuing these sexual mavens, was high on a pirate's list of priorities. This meant visiting taverns, any low-class areas that served drink, or brothels disturbingly known as punch houses. In Port Royal, one visitor famously touted that these establishments featured “such a crew of vile strumpets and common prostitutes that 'tis almost impossible to civilise.”

Port Royal was particularly overrun by working girls. One whorehouse teeming with treachery was that owned by John Starr, who featured twenty-one Caucasian women and two African-American women. Among Port Royal's wenches was the infamous Englishwoman Mary Carleton, dubbed “The German Princess.” Her self-proclaimed status as a German princess came about as a result of fraud, after she married John Carleton in London during the 1660s. After a trial and subsequent acquittal, she wrote and acted in a London theatrical play about herself.

Carleton's ruses, however, endured for the next decade as she continued her fraudulent portrayals in order to lure and rob various men of their money. Eventually sentenced for bigamy and various thefts, she was transported to Port Royal in 1671. Not a woman to sit still for long, she found pirates and other scoundrels to be easy prey. Sources describe Mary as “common as a barber's chair: no sooner was one out, but another was in.” Carleton's wicked ways eventually caught up with her and after returning to England without permission in 1673, she was finally captured and summarily hanged.