Ahoy, mateys! Did you know it’s National Talk Like a Pirate Day? Our friends at CheapCaribbean sure do, as they’ve just dropped the details of their new Pirate Tour of Panama and Colombia.

Running December 6th through December 11th, the trip is a unique opportunity to experience tropical adventure, learn pirate history, lodge at fantastic resorts and, like a prosperous pirate, enjoy plenty of good food and drink.

We got a chance to sneak preview this sojourn recently, and it rocked. Spy some highlights and trivia below—#8 will shock you—and remember, it’s all fun and games even when someone loses an eye.


Our adventure began at Dreams Delight Playa Bonita Panama, a delightful resort located right next to the water. We’re not huge tropical cocktail fans, but the piña coladas by the pool are tough to beat. Cocktail Party Fact #1: The resort has some great local rums to get you in a pirate frame of mind, too, most notably Ron Abuelo.


One of our first stops on the tour was the charming coastal town of Portobelo. Not only is it home to a kickass seafood restaurant and lodge called Coco Plum, but it’s also loaded with pirate history, thanks to visits by guys like Francis Drake and Captain Henry Morgan, who was, in fact, a real person—with a sweet mustache to boot. Cocktail Party Fact #2: After a wildly successful pirating career, Morgan spent the last few years of his life getting blitzed on rum before cirrhosis of the liver finally sunk his ship. Very on brand! The major claim to fame of Portobelo, however, is the famed Black Jesus that people travel from miles around to visit and festoon with fancy outfits on special occasions. No word yet whether he was the inspiration for Madonna’s “Like a Prayer” video.


One of our favorite things about Panama was a visit to the old city, which is quite lively on a Saturday night. We hit several cool bars, made lots of new friends and took a series of photos of such low quality they aren’t really worth sharing here. Cocktail Party Fact #3: American money is legit currency here, although you may occasionally receive change in Panamanian coins. During the day we paid a visit to La Taberna Morgan (because of course), which is a bit like the Tilted Kilt but with more pirate memorabilia. The ribs there are about as big as a peg leg, too.


You can’t visit Panama without checking out the Panama Canal, and it’s really quite a marvel to behold. While big ships must pay literally millions to pass through it, you can take a small sailboat through for as little as two grand. Score! Cocktail Party Fact #4: Panama hats actually come from Ecuador, but got their name in part because President Teddy Roosevelt was photographed wearing one whilst inspecting the construction of the Canal in the 1900s.


After a few blissful days in Panama, we were off to Colombia, where we stayed at the absolutely stunning Conrad Cartagena. With majestic rooms, a killer breakfast buffet and pools of all different depths and temperatures, you’ll have to drag yourself off the property, but it’s worth it because the city of Cartagena and the surrounding area is a blast. Cocktail Party Fact #5: For less than $100 USD, you can rent a fun little motorcycle for a day, ride to and bathe in an actual volcanoWe know because we tried.


Like most big cities, Cartagena is home to some excellent restaurants, the most impressive of which has to be La Vitrola. The eatery’s shrimp dishes are truly spectacular, and the desserts are tasty, too. Cocktail Party Fact #6: Club Colombia is the beer of the realm, available just about anywhere. Yes, it tastes a bit like Budweiser, but it’s quite refreshing on a balmy day—or night.


Cartagena is a great place to see an impressive pirate ship replica, in this case El Galeón Bucanero. This particular ship also serves food and drinks, puts on a colorful pirate-themed dance performance and houses a decidedly wacky pirate museum on the lower deck that we kinda loved. Cocktail Party Fact #7: The real upside of Drake’s 1586 capture of Cartagena? The birth of the mojito, whose ingredients were picked up in Cuba slightly after the raid and combined into a fever remedy known as El Draque. It proved… effective.


One final highlight of the Cartagena leg was a boat tour of several defensive fortifications dating back centuries, including the Castle of San Felipe, Fort of San Fernando, Fort of San Jose and more. Just strolling around these spots and imagining what it must’ve been like to do battle nearly 500 years ago is a real head trip. Oh, and the warm blue water makes for quite a refreshing swim, too. Cocktail Party Fact #8: Legend has it, not all patch-wearing pirates were actually missing an eye. Some merely used them to adjust to light changes when commandeering another vessel and descending into the darkness below decks. 

To plan your own buccaneering adventure, visit legendsofpiratespast.com.


Photos: Panama Canal, Getty Images/Marian Stoev/EyeEm; El Galeón Bucanero, Getty Images/User10095428_393