History has recorded acts of piracy at sea as early as the 14th century BCE. Piracy was a fairly commonplace way to make ends meet, and most countries that border water (I see England, I see France…) have, at some point, indulged in a little ship-to-ship goods borrowing. And sure, pirates may have been bloodthirsty nomads, but they did get one thing right: location, location, location.

The fact that so many pirate havens were located in the Caribbean might have had more to do with the islands’ proximity to Spanish outposts than with any desire for a tropical holiday. But why not mix business with pleasure? We’re certain the Caribbean’s turquoise seas, soft breezes and all those fruity cocktails only helped sweeten their swindles. (They did have fruity cocktails in ye olden days, did they not?).

Inspired by the epic, the daring and the extraordinary journeys undertaken by pirates throughout history, Playboy brings you a list of fantastic journeys to follow in the wake of the best pirate adventurers around the globe. These pirate escapades are as fun for landlubbers as they are for the aquatically inclined. Come as you are with your yo-ho-ho and a bottle of hooch. Get your swashbuckle on (or just your regular buckle) and follow the intrepid adventures of the lawless rumrunners of yore.


JAMAICA © 2014 Hilton Hotels & Resorts

JAMAICA © 2014 Hilton Hotels & Resorts

A beautiful island ideally positioned off the southern tip of Cuba and just west of Haiti, Jamaica was the perfect home base for pirates hoping to plunder Spain’s New World gold. So appealing, in fact, that pirates had the run of the place: an entire contingent of buccaneers, privateers and pirates operated out of Port Royal, on Jamaica’s southern coast. Once it started to gain fame as a pirate haven, the town boasted such establishments of ill repute as brothels, taverns and drinking halls. Largely manned by pirates and buccaneers, Port Royal was one of the busiest, and most infamous, ports in the Americas. Although Port Royal never really recovered its grandeur after a 1692 earthquake, there is still a town there today. Some old buildings remain intact, and it’s worth a trip for history buffs. You’ll definitely want to see all Jamaica has to offer, from Kingston’s roaring nightlife to Negril’s party beaches…and beyond! But be sure to make time for a few historic stops.

WHAT TO DO:Book a table at the Bloomfield Great House and linger over a long meal. Once part of a coffee plantation, today this restaurant serves one of the island’s best-orchestrated menus. Smoked marlin with black caviar? Yes, please.

WHERE TO STAY: Luxury meets history at Rose Hall Plantation. Nestled between the scenic mountains and turquoise Caribbean waters of Jamaica, the all-inclusive Hilton Rose Hall Resort & Spa inhabits an exclusive oceanfront location on the edge of Montego Bay. Their contemporary beachfront accommodations set on the legendary 18th century Rose Hall Plantation evoke the colorful charm and hospitality made famous by the island, and all rooms feature a private balcony or terrace. Look out for the ghost of Annie Palmer, known as the White Witch, who they say haunts Rose Hall… Book it HERE.

Punta Cana: Gabi Beach

Punta Cana: Gabi Beach


When you think pirates, you think blue oceans, tropical islands and coconut palms. Lucky for you, then, that walking in the footsteps of notorious pirate Captain Kidd will take you to the sunny Dominican Republic. William Kidd was born in not-so-sunny Scotland in 1645 and actually began his naval career as a pirate hunter before being accused of piracy himself, tried and executed in England. But for hundreds of years, his ship, the Quedagh Merchant, was never found…

WHAT TO DO: …until 2007, when the wreckage of Kidd’s ship was discovered off the coast of the Dominican Republic. The shipwreck has been turned into an underwater museum near Catalina Island. Strap on your diving gear and check out the notorious pirate’s ship among the coral. Get the intel HERE.

WHERE TO STAY: You’re not exactly hurting for hotels in the Dominican Republic, a small country that features any number of all-inclusive resorts. Our choice: The Reserve at Paradisus Palma Real in Punta Cana. Located on Bavaro Beach, one of the finest beaches in the world, this resort has every luxury amenity you could ask for. Find out more HERE.

"Pirate Museum," © 2009 Greyloch, used under a CC Attribution license

“Pirate Museum,” © 2009 Greyloch, used under a CC Attribution license


The first recorded history of the Bahamas is when Christopher Columbus set foot on the island in 1492, on his first voyage across the ocean blue. Seeing much the same history as Jamaica, the Bahamas became overrun with pirates. At least 20 pirate captains based their operations out of Nassau or other towns in the Bahamas during the 18th century, provoking brutal attacks by the French and Spanish. Today the locals engage in far more prosaic pursuits, but the island breathes history.

WHAT TO DO: Nassau was the epicenter of piracy during its golden age. Learn more about Nassau’s pirate history at the Pirates of Nassau Museum, where you can board a replica pirate ship and even meet fearsome female pirate Anne Bonny herself. Get all the details HERE.

WHERE TO STAY: The Tiamo Resort is located in a sheltered cove any pirate would have loved as a home base, but it provides a level of luxury they could never have dreamed of. It’s accessible only by boat or seaplane, which makes it the perfect hideaway. This is one tropical island you’ll be dying to get marooned on. Book your stay HERE .

© 2014 Calabash Cove

© 2014 Calabash Cove


You must see the beautiful Saint Lucia for yourself. One of the Caribbean’s Windward Islands, it is so lovely it was fought over by the English, French, Spanish and Dutch for 26 years, which gave it the name La Belle Helene, after Helen of Troy. The island’s very first European resident, Francois Leclerc, was—you guessed it—a pirate. Not just any pirate, but a pirate with a proper wooden leg, which is why he was called “Jambe de Bois,” or in English, Old Peg Leg. He hid out on Saint Lucia’s historic Pigeon Island, a 40-acre islet located on the island’s northernmost point, using it to target Spanish treasure galleons. Today a national landmark with the Saint Lucia National Trust, Pigeon Island is home to the Saint Lucia Jazz Festival and makes for an idyllic historical tour—visit the ancient fortifications and canons and get a feeling for Saint Lucia’s vibrant history.

WHAT TO DO: Saint Lucia is gorgeous enough to just enjoy for its own sake. But if you want to up the ante, pirate style, why not charter a sailboat and weave your way through the Windward Islands? Book your adventure HERE.

WHERE TO STAY: Just because Old Peg Leg didn’t care for fancy digs doesn’t mean you have to follow in his, er, footstep. We recommend you stay at the luxury boutique hotel Calabash Cove. Tucked away on the northwest coast of the island, Calabash Cove sits on a hillside that looks out to the Caribbean Sea and views of Walcott Island. Its private beach, sheltered by a nearby coral reef, provides the perfect destination to rest and dream of the pirate life. Book your stay HERE .