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RSW Living Magazine

Arrr!! Cruising with Florida’s Pirates: Find Adventure Aboard Pieces of Eight

It’s like living out your own real-life Pirates of the Caribbean fantasy, except you don’t even have to leave Southwest Florida to set sail on an unforgettable journey of history, suspense and adventure. 

Since 1999, Salty Sam's Waterfront Adventures has offered its famous Pirate Cruise, setting sail from Salty Sam's Marina on Fort Myers Beach. These days, the Pirate Cruise is hosted on board a ship aptly named Pieces of Eight, a reference to Spanish currency that was once highly sought after (and for good reason!). 

“Pirates plundered many Spanish galleons in search of pieces of eight,” explains David Kastan of Salty Sam’s. “Just a handful would have been worth a small fortune to any pirate!”

When you step on board Pieces of Eight, you’ll find more than treasure. You’ll experience a world where pirates make the rules, and if you break them, you’ll walk the plank! 

Built in 2005, Pieces of Eight is a replica Spanish galleon, measuring 65 feet long and 25 feet wide, weighing 79 tons, and powered by twin diesel engines. The ship is big enough to fit 100 hearty pirates. 

During each 90-minute cruise, passengers can interact with the pirate crew, explore the upper and lower decks of the ship and partake of snacks and beverages. The family cruise offers face painting, dancing, limbo and pirate games.  

Each cruise is also a lesson about Southwest Florida’s rich history and strong connection to pirates, the bandits of the sea. “Two of the most famous pirates in Southwest Florida were Henri Caesar, known as, ‘Black Caesar,’ and Jose Gaspar, known as ‘Gasparilla,’” says Kastan, adding that Captiva Island is so named because Gaspar is said to have held female captives for ransom there. 

“Southwest Florida was a staging area for Spanish ships, filled with untold quantities of gold, jewels, exotic woods, spices and tobacco,” explains Kastan. “They were ultimately bound for Spain. The stories of wealth being plundered from the Americas and Caribbean attracted the interest of brigands, with dreams of their own wealth.” 

That love of treasure is reflected in the nicknames of the Pieces of Eight pirates, such as “Pickpocket Pete,” who together with his shipmates creates an atmosphere of fun, excitement and inclusion aboard the pirate ship, making sure pirates of all ages enjoy the experience. 

Prices for the 90-minute cruises are $29.95 for adults and $24.95 for kids. Salty Sam’s also offers adults-only cruises and private charters aboard Pieces of Eight. When it comes to paying your way, modern payments are preferred. “We accept cash or credit, but not your children!” says Kastan. 



Salty Sam’s Pirate Cruise
2500 Main Street, Fort Myers Beach

Written by Nick Ciletti, a contributor to TOTI Media. He spent three years in Southwest Florida and now lives in Phoenix, Arizona.