Pirate Paradise: 8 Essential Stops for Buccaneers in Florida

No lesson on Florida’s maritime history is complete without mentioning the pirates that once prowled its coastline. From museums packed with centuries-old artifacts and underwater shipwrecks to pirate cruises along the coast, the Sunshine State is a prime spot for a swashbuckling good time for the whole family.

1. Pirate & Treasure Museum – St. Augustine

Buccaneer’s Bounty

One of the nation’s oldest settlements, and once a pirate stronghold, is the perfect start to any Buccaneer-themed itinerary. This collection of pirate artifacts, curated by entrepreneur and self-described “pirate scholar” Pat Croce, is considered one of the world’s largest and most authentic. Guests wander through life-size replicas of a ship’s cannon deck, pretend to steer the vessel behind a massive captain’s wheel, and play interactive games. Don’t miss a look at infamous pirate Blackbeard’s blunderbuss (that’s a pirate’s firearm to all of you landlubbers) and pieces of gold from his ship, a real Jolly Roger flag with its iconic skull and crossbones dating to 1850, and the world’s only known surviving treasure chest, one owned by 17th century pirate Thomas Tew. Take your time and explore more than 800 artifacts on display, with a little fantasy thrown in for good measure.

2. The Pirate Ship at John’s Pass – Madeira Beach

Set Sail

Even the littlest rascals will have a blast aboard the two-level, 46-foot Royal Conquest pirate ship as the crew sets sail in Boca Ciega Bay. This entertaining-not-scary cruise is hosted by a costumed captain and two friendly mates in full pirate regalia who lead guests in water gun battles, play music, encourage dancing, and paint faces. In true sea rover tradition, the crew tells tall tales about the pirates who once roamed the area. Every child receives a paper hat, beads (even small sailors need some treasure!) and an honorary pirate certificate signed by Captain Driftwood himself.

3. Gasparilla Pirate Festival – Tampa

Pirate Paradise

Inspired by swashbuckling Spanish pirate José Gaspar, sometimes called Gasparilla, who supposedly ruled the waters from northern Florida to Cuba in the late 18th and early 19th centuries, this festival has been delighting revelers of all ages since 1904. Every year on the last Saturday in January, hundreds of boats converge on Tampa Bay, led by the world’s only purpose-built pirate ship, José Gasparilla II. With the ship’s colorful flags flying, its enthusiastic crew of merry misfits, dubbed Ye Mystic Krewe, disembarks to lead a parade of more than 100 festooned floats down Bayshore Boulevard on the way to symbolically retake the keys to the city from the mayor. Each year, this signature event draws more than 300,000 revelers, dressed in their best pirate attire. Though historians have found no evidence that Gaspar existed in the flesh, this piece of Floridian folklore is pure fun.

4. Salty Sam’s Pirate Cruise – Fort Myers Beach

Swashbuckling Sail

Join the crew aboard the 65-foot replica Spanish galleon, Pieces of Eight, for a 90-minute excursion in the glittering Gulf waters off Estero Island. Designed to harken back to piracy’s Golden Age when fierce buccaneers roamed the coast. These days, friendly costumed crew members recount pirate legends, lead a dance party, and direct an on-ship treasure hunt. If you’re lucky enough to visit in the evening, look west for a spectacular sunset over the waves. Note to families: Salty Sams offers adults-only excursions (where the rum-laced grog flows), so be sure to book an all-ages trip for your littlest crew members.

5. Alligator Reef Lighthouse – Florida Keys

Ramblin’ Wreck

Hook up with a local captain and set sail from Islamorada due west in search of the hauntingly beautiful Alligator Reef Lighthouse, four nautical miles offshore. While the waters aren’t inhabited by any ‘gators, the spot is named for the USS Alligator, a Navy schooner built in 1822 and dedicated to patrolling Florida’s waters and recapturing ships pirates had stolen. Shortly after taking to the open water, the ship ran aground on a reef and sank. In 1873 the 133-foot-tall lighthouse was erected to help other sailors navigate the tricky waters. These days, it’s a popular spot for snorkelers and divers to explore its striking turquoise waters where they’re likely to see colorful coral, parrotfish, spiny lobsters, and much more. For those who prefer to see without getting wet, local outfitter Robbie’s of Islamorada offers a tour on a glass-bottomed boat.

6. Captain Memo’s Original Pirate Cruise – Clearwater Beach

Shiver Yer Timbers

This family-friendly pirate ship has been leading swashbuckling sails in Clearwater since 1977. Once on the open water, the littlest mateys can have their faces painted in fierce designs, engage in water gun fights, and search for hidden treasure in the ship’s nooks and crannies. Parents can take turns visiting the adults-only third deck for a tipple from the captain’s bar, and everyone is encouraged to dance to the pirate-approved tropical tunes piping through the thoroughly modern speakers. The two-hour cruise has spectacular views of the Gulf of Mexico and the cheerful (and playfully salty) crew is happy to help guests spot resident dolphins frolicking in the waves.

7. Pirate’s Cove Adventure Golf – Orlando

Mini-Golf Mateys

Encourage some healthy family competition at this pirate-themed miniature golf course. Choose from two 18-hole courses (or go wild and tackle both), named for historic privateers Captain Blackbeard and Captain Kidd. No matter which challenge you accept, you’ll see a replica pirate village full of creative, moving obstacles that make it challenging to get the winning shot. Your family members will putt their way through a massive replica pirate galleon festooned with cannons and barrels of booty, under rushing waterfalls, and over rope bridges.

8. Buccaneer Pirate Cruise – Destin

Salty Dogs Welcome

Live a pirate’s high life aboard the Buccaneer, a majestic 100-foot galleon fit to rule the high seas. You’ll embark on this family-owned excursion in Destin’s HarborWalk Village and experience the excitement of pirate basic training where you’ll learn the lingo and legends, and engage in playful sword battles, water gun fights, and treasure hunts, all led by the costumed crew. Enterprising little plunderers may get tapped to swab the decks in their quest for honorary Buccaneer crew status. Get ready for a big “boom!” when live cannons fire from the ship’s sides as the pirate flag flies.