The Real Pirates of the Caribbean

Take a look at the Caribbean hots spots once frequented by real pirates, including Edward Teach (Blackbeard), Calico Jack Rackham, Roberto Confresi and Jon Boysie Singh.

Photo By: By Raychristofer (Own work) [CC BY-SA 4.0], via Wikimedia Commons

Photo By: goldistocks/Getty Images

Photo By: Wikimedia Commons

Photo By: By Pascalou petit (Own work) [GFDL or CC BY-SA 3.0], via Wikimedia Commons

Photo By: Noel Hendrickson/Getty Images

Photo By: By Bryce Edwards from San Jose, CA, USA (Bahamas GazeboUploaded by Tomer T) [CC BY 2.0], via Wikimedia Commons

San Juan

Roberto Cofresi aka El Pirata Cofresi was shot by a firing squad in San Juan, Puerto Rico. Confresi commanded a crew to attack primarily cargo vessels responsible for exporting gold.

Port Royal

Pirate history buffs believe Port Royal, Jamaica, is a must-see Caribbean destination. It was once the pirate capital of the Caribbean. The British, based at Fort Charles, actively encouraged and even paid buccaneers based at Port Royal to attack Spanish and French ships in the 1600s. Fort Charles is the last of 6 forts that still exist as a tourist attraction.

Emerald Falls

Enjoy the lush surroundings of the Emerald Pool on Dominica, a famous pirate haunt in the Caribbean. Most of the movie Pirates of the Caribbean was filmed in Dominica and Nassau.


Aruba is a great place to watch the sun set while having dinner with the one you love, but you can also take a cruise on Aruba's Jolly Pirates Ships with the family. Get a quick pirate history lesson and enjoy snorkeling in old pirate hot spots.


Edward Low, one of the most brutal and vicious pirates in the 1700s, was hanged in Martinique. He captured over 100 ships, and he and his crew murdered, tortured and maimed hundreds of people.

Pirate-Themed Sailing

You can't understand a pirate until you've sailed a mile on his boat. Take a cruise with Windjammer or Star Clipper, both offer pirate-themed sailing adventures. It's OK to drop anchor and take a swim, too.

Port of Spain

John Boysie Singh, known as 'the Rajah,' was born and later hanged in 1957 in Port of Spain, Trinidad, for the murder of his niece. Singh had a long career as a gangster and gambler before turning to piracy and murderer, terrorizing and killing 400 people on boats that traveled between Trinidad and Venezuela.


Don an eye patch, down some rum and yell 'Ahoy, me hearties!' Hundreds of travelers head to the Georgetown harbor in the Cayman Islands for the Pirates Week Festival. The fun festival includes street dances, music, treasure hunts and parades.

New Providence

Several years ago, we're sure pirates passed by this entrance to the Nassau harbor in New Providence, Bahamas. New Providence was a haven for nefarious pirates including Charles Van, Calico Jack Rackham and Edward Teach aka Blackbeard. A walking tour in Nassau is a great way to explore real pirate history.

Sunken Shipwrecks

Several tour companies and cruise lines offer shipwreck tours or snorkeling excursions to travelers who want to explore sunken ships in key Caribbean destinations, including Aruba, Roatan Island (Honduras), Buck Island (St. Thomas) and Barbados.

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