This is Arr-gust, which also is known as International Pirate Month. It’s a month-long, swashbuckling celebration observed every August, dedicated to pirate lore, fictional sea adventures, historical trivia of the Golden Age of Piracy, and all things “yo ho ho!”
Over the years, Arr-gust has become an unofficially observed global celebration embraced by communities, libraries, and pop-culture enthusiasts. It encourages people to dive into the lore of real-world figures like Blackbeard and Calico Jack, or classic tales like Treasure Island.
Here in Florida, our complex coastlines and heavily trafficked shipping channels made it a prime haven for pirates, privateers, and buccaneers between the 1500s and early 1800s. These outlaws constantly preyed on vulnerable Spanish treasure fleets sailing the Gulf Stream and navigating the Gulf Coast.
Some Famous Privateers
Haunting the Sunshine States shores were famous such as Sir Francis Drake, the famous English privateer famously raided and burned the early Spanish settlement of St. Augustine to the ground. Black Caesar, a legendary African chieftain turned pirate who operated from Caesar’s Rock near Elliott Key in the Florida Keys. He eventually joined forces with the infamous Blackbeard and was captured by the British navy.
Possibly the most famous of the privateers is José Gaspar who based his operations out of Charlotte Harbor. Though modern historians note he is largely a figure of folklore, his legend is celebrated annually at the massive Gasparilla Festival held annually in Tampa.
Set Sail Yourself
For those who want to celebrate the month, there are ample opportunities in the forms of sailing ships, museums and event golf outings. (August also is Golf Month – but more on that later.
For those who wish to set sail, you might try Captain Memo’s Pirate Cruise. Ported at the Clearwater Municipal Marina in Clearwater Beach, the Pirate’s Ransom is a 70-foot galleon replica. Built in 1993, they have a two-hour daytime family adventure. The trip features water gun battles, treasure hunts, face painting and pirate stories.
It includes complimentary beer, wine, or non-alcoholic drinks.
There’s also a Sunset Champagne Cruise. A scenic Gulf of Mexico sunset sail that includes all the daytime pirate activities for families plus free champagne alongside beer and wine.
If you’re up near St. Augustine, Black Raven Adventures might be your ticket.
The Black Raven is described as a “floating pirate theater ship. This cruise provides a live theatrical performance featuring sword fights, cannon firings, sea shanties, and an interactive plot where kids battle Captain Blackbeard to reclaim stolen treasure.
They also feature a two hour “Tropical Sunset Cruise.” This consists of an all-ages, relaxed Caribbean-themed sunset cruise along Matanzas Bay with light games, music, and scenic coastal views.
Additionally, for the adults, there’s the Rum Runner Cruise. It’s an adults-only “booze cruise” featuring crude pirate humor, adult games, live interactive performance, and a full bar.
The Buccaneer Pirate Cruise sails out of the Harbor Walk Village in Destin. This 100-foot, triple deck galleon replica give an interactive pirate cruise that also runs about two hours. This broad-deck family voyage sails through the Choctawhatchee Bay with sword fighting lessons, water cannon battles, treasure hunting, face painting, and dolphin spotting.
They also offer a Sunset Family Pirate Cruise which combines the full interactive kid-friendly pirate show with Emerald Coast sunset views and golden-hour photography.
A bit further south, is Salty Sam’s Pieces of Eight cruise, out of Salty Sam’s own marina in Fort Myers Beach. The Salty Sam – a 65-foot Spanish galleon replica runs a 90-minute family pirate cruise which sails through Matanzas Pass into the Gulf of Mexico. There’s face, water cannon duels, possible dolphin sightings and even a mutiny (don’t worry, you’ll get back OK). For those who want it, there’s a full cash/card bar available onboard.
There’s also a saltier, “Pieces of Eight” Cruise. This is an adult-only, evening party cruise featuring adult-oriented pirate comedy, music, and drink specials.
If you cannot wait for the Gasparilla, the 60-foot Lost Pearl Pirate Ship sails out of downtown Tampa – departing near the Tampa Convention Center / Riverwalk. There’s an All-Ages Pirate Adventure Cruise which navigates the Hillsborough River and Tampa Bay. Passengers become ersatz crew members with interactive swab-the-deck training, water cannon battles against rival pirates, and games.
Watching the sun go down over the Gulf is easy with the Tampa Sunset Pirate Cruise This is an all-ages sunset sail across Tampa Bay featuring pirate games, music, and full cash bar for adults.
Not so very far away is The Royal Conquest. A 46-foot, two level vessel, she sails out of Madeira Beach / St. Petersburg at the John’s Pass Boardwalk. This Pirate Adventure Cruise sails through Boca Ciega Bay. They feature limbo contests, treasure hunts, water gun fights, pirate stories, and dolphin viewing. It includes complimentary soft drinks and water, with optional all-you-can-drink adult beverage packages.
The Pirates of Marco Island are found on the The Black Pearl. It’s a 60-foot custom pirate vessel that sails out of the Rose Marina. Unlike some of the others, this one runs about an hour, and is described as a high-energy, fast-paced 1-hour cruise tailored for younger children where they battle “Pirate Pete” with water cannons to retrieve a sunken key.
For something a bit more relaxing, there’s also the Black Pearl Sunset Cruise. That’s a scenic, relaxed evening sail into the Gulf of Mexico toward the 10,000 Islands, featuring music and a full onboard bar. It runs about 90 minutes.
With any and all of these tours, we suggest you look for sailing times, and special provisions for any of the cruises.
Other Pirate Opportunities
What’s that you say matey? You get seasick? Well Florida also features a wide variety of Pirate Outfitter Shops & Maritime Museums for landlubbers who identify as privateers. For instance, there’s the Antilles Trading Company inHistoric Cocoa Village. Widely known as “The Pirate Store & Museum,” this coastal staple caters to buccaneers of all stripes. It features curated historical weapons, period apparel, nautical antiques, and authentic artifacts alongside costume gear for pirate enthusiasts.
St. Augustine Pirate & Treasure Museum in St. Augustine is situated directly across from the historic Castillo de San Marcos. This interactive museum houses over 800 authentic Golden Age pirate artifacts, including one of the world’s only surviving original Jolly Roger flags and Thomas Tew’s authentic treasure chest.
Tampa Bay History Center at the Tampa Riverwalk offers extensive permanent exhibits detailing Florida’s actual 17th- and 18th-century maritime history, privateers, and the legends surrounding Gulf Coast freebooters like José Gaspar.
If you’re a hungry buccaneer, there’s Orlando’s Pirate Dinner Adventure. A large-scale indoor theatrical show anchored by an 18th-century Spanish galleon inside a 300,000-gallon indoor lagoon—complete with acrobatic sword fights, pyrotechnics, and cannon blasts.
And as we said earlier, August also is Golf Month. You can get a twofer by visiting any of the Pirate’s Cove Adventure Golf locations statewide. A classic landlubber option featuring multi-level mini-golf courses built around waterfalls, pirate ships, and treasure caves.
In any event, Florida gives us multiple opportunities to celebrate Arr-gust, and Highlands County is uniquely situated in the center of the state, making it an easy drive to the Gulf or the Atlantic. Heck, make it an overnighter, and seek ye some buried treasure.
