Weigh Anchor and Hoist the Mizzen for These Bonny Caribbean Pirate Experiences

  • 01 of 10

    Avast Ye! Here There Be Pirates!

    Pirate flag

    Piracy and the Caribbean go together like parrots and pirates, so the next time you venture down to the islands, be sure to spend a little of your vacation booty on one of these freewheeling buccaneer adventures!

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  • 02 of 10

    Pirates Week Festival, Grand Cayman

    © Don McDougall

    Can’t get enough pirates? For all the swashbuckling fun you could possibly ask for, check out the 11-day long National Pirates Week Festival in Grand Cayman, featuring a mock “pirate invasion,” as well as displays, demos, and fireworks! 

    A one of a kind Caribbean event, the Pirates Week Festival invites all guests to dress up in their best pirate gear and compete in various competitions and events to prove that they are the rightful rules of the Seven Seas! Combining history with fun, this festival highlights the history of pirates in the Caribbean and lets all participants channel their inner Jack Sparrow. 

    Festival takes place in November and spans 11 days, featuring both adult and family-friendly events each day and evening, and features on-land and off-land events, for sea-lovers and landlubbers alike.

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  • 03 of 10

    Pirates of the Caribbean Fun Tour, Dominica

    Trafalgar Falls, Dominica
    Photo by Anthony Quintano/CC by 2.0

    Want to feel like you’re a part of the Pirates of the Caribbean cast and crew? Look no further than Dominica, a past real-life pirate port and a verdant tropical oasis that served as the set for much of the Pirates of the Caribbean film series. 

    Sheppee Fun Tours meets you dockside in Roseau for incoming cruise ships to take you on the “Pirates of the Caribbean Fun Tour,” a walking tour that takes travelers through several areas featured specifically in Pirates of the Caribbean: Dead Man’s Chest, including Ti Tou Gorge, Trafalgar Falls, and Champagne Beach. Throughout the tours, guests will also learn about Dominican culture and history, and be able to spend some time exploring Dominica’s diverse terrain, including mountain region, downtown, and the Botanical Gardens.

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  • 04 of 10

    The Pirates of Nassau Museum

    Iron maiden at the Pirates of Nassau museum
    © Daniel Dudek-Corrigan/CC by 2.0

    For a comprehensive look at the Caribbean’s epic pirate history and lore, check out the Pirates of Nassau museum in the Bahamas. Sure, the settling looks a little cheesy, and you can buy ti-cornered hats and plastic cutlasses in the gift shop, but the museum itself is actually quite well done, with some cool interactive displays and unvarnished research on what the real lives of pirates were like. The setting makes sense, too: Nassau was a major pirates haven during the 18th and 19th centuries for one very important reason: the harbor was deep enough for most pirate boats but too shallow for the big warships that chased them. The museum is an easy walk from Nassau’s busy cruise port, and the price — $13 for adults, $6.50 for kids — is less than the high-seas robbery you’d expect at most tourist traps.

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  • 05 of 10

    Tropical Pirates Eco Tours, Puerto Rico

    Statue of pirate Roberto Cofresi in Puerto Rico

    Another popular site in the Pirates of the Caribbean series, Puerto Rico is a country with a history that is heavily endowed with pirates and piracy, especially at the height of sea travel and trade. 

    When visiting Puerto Rico today, tourists can explore the island and its pirating history by boat with Tropical Pirates Eco Tours, led by “Captain Carlos,” or choose to paddle their own kayaks for an individual pirate experience in a group setting. On this tour, visitors not only see Puerto Rico from a unique, in-boat point of view, but they also learn about the history of pirates throughout the West Indies, especially the notorious Puerto Rican pirate Robert Cofresi (“El Pirata Cofresi”), and his various conquests across Caribbean in the 19th century. And, since it is rumored that Cofresi’s treasure is still buried somewhere in Puerto Rico today, travelers may just find more than they bargained for as they explore the native waters and the caves that Cofresi once walked himself.

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  • 06 of 10

    Fort Charles Maritime Museum, Port Royal, Jamaica

    Fort Charles, Port Royal, Jamaica
    Photo © Raychristofer/CC by SA 4.0

    Known as the pirate capital of the Caribbean, Port Royal, Jamaica is a must-see sight for any landlubbers looking for an experience that will make them shiver their timbers. 

    To learn about the history of piracy in Port Royal, visitors can check out the Fort Charles Maritime Museum and Fort Charles itself, one of the last standing forts in the Caribbean and a prime location for spotting incoming pirate ships in the Golden Age of piracy in the 17th and 18th centuries. 

    The Maritime Museum, which is open from 10AM to 4PM daily, details the history of Port Royal, the “Wickedest City on Earth,” including the rise and fall of pirates in the West Indies as well as the devastating earthquake that shook Jamaica and nearly knocked out pirating in the region for good. 

    History buffs and pirate lovers alike can also explore Fort Charles during museum hours, and revel in the artifacts of the Royal Navy and the old British naval headquarters from the time when the world was ruled from the sea and pirates lived to challenge the power of their fellow captains and sea-dogs.

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  • 07 of 10

    Captain Jon Blac Pirates of St. Kitts Tour

    treasure island

    An island tour that focuses on the history of pirates, from the early years, through the Golden Age, to the present, the Captain Jon Blac Pirates of St. Kitts Tour offers a unique learning experience about the impact of pirates on the economy and society of the West Indies. For literary types, this tour lets visitors see the setting of the recently released book by John Amrhein, Jr. entitled Treasure Island: The Untold Story, a novel that focuses on the history facts and events that would have surrounded Robert Louis Stevenson’s famous pirate story, Treasure Island. 

    Hosted by Culture House Accommodations in St. Kitts & Nevis, the Captain Jon Blac Pirate of St. Kitts Tour tour meets daily in Conaree Bay and allows visitors to experience the island of St. Kitts from a personal perspective via walking tour.

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  • 08 of 10

    Blackbeard’s Revenge Pirate Schooner, St. Thomas

    capture of blackbeard

    Set sail on your own pirate adventure with the Blackbeard’s Revenge Pirate Schooner, a 65-foot ship with all the swashbuckling fun and excitement of a real pirate’s rig. Designed to replicate the pirate ships of the 17th and 18th century, this schooner makes its way around St. Thomas’s Caribbean waters, traveling through destinations including Buck Island, Turtle Cove, Shipwreck Cove, and St. John’s National Park waterways. On the journey, travelers will hear pirate stories and learn about island history, while the signature red sails are hoisted and the pirate adventure begins! 

    While on board, visiting crew members will have the opportunity to get their own (temporary) pirate tattoos, take a swig of some rum bunch, and snorkel in the Caribbean waters alongside turtles and fish. Who knows, maybe they will find some buried treasure along the way!

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  • 09 of 10

    The Jolly Pirates of Aruba

    Rope swinging with the Jolly Pirates
    © Jolly Pirates

    There's room in our pirate soul for a "pirate ship" experience that's mostly about fun, and that ship belongs to Aruba's Jolly Pirates. Setting sail from popular Palm Beach, these scalawags will get you dancing on the deck with your best mateys in no time, with lots of grog (even if you've already found your sea legs, they ply you with enough potent rum punch to turn your swagger into stagger in no time), snorkeling stops, and the opportunity to "walk the plank" aided by a rope swing -- big style points for the best leap!

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  • 10 of 10

    Pirates in Paradise, Key West

    © Monroe County Tourist Development Council

    Set sail for jolly Key West this (and every) December for the annual Pirates in Paradise festival. Key West knows how to do theme parties right — there’s even one dedicated to Ernest Hemingway that attracts Papa look-alike from around the world — so you know this free-spirited town embraces the pirate mentality whole-haaaarrtedly. Dress up as your favorite swashbuckler to enjoy a weekend of themed sailings, an invasion of Fort Zachary Taylor, a Walk the Plank contest, and — this being Key West — a competition for Most Buxom Wench and Bad Ass Pirate.