Trail of the Pirates is a travel series exploring maritime history, culture and lore between Key West and St. Augustine on the east coast of Florida.
Skeleton and Caribbean Pearl strike a pose for Trail of the Pirates.
Trail of the Pirates came full circle this month when I covered the Pirates in Paradise Festival and the Fort Taylor Pyrate Invasion on the first weekend of December. I couldn’t attend last year as the Key West event runs back to back to the St. Augustine Pirate Gathering and I had already been on the road for days interviewing, researching and learning as much as I could about pirate and maritime history on the east coast of Florida.
PIRATES HIT BONE ISLAND AKA "CAYO HUESO"
It doesn't get better than this. Sailing in Key West with pirates singing sea shanties and firing weapons with gun powder!
Pirates in Paradise is a week-long festival with costume contests, storytelling competitions, musical performances, pirate sailing trips, walk-the-plank competitions, a pirate pub, pirate tours of Key West and more. The main festival grounds are at the Truman Waterfont Annex.
Next door at Fort Zachary Taylor you’ll find the Pyrate Invasion, which features a more traditional encampment recreating the Golden Age of Piracy (1675-1825). Over three days, the fortress becomes an English stronghold where British Red Coats battle against pirates with real cannons and gun powder. Living history demonstrations allow visitors to meet well-established captains and crews.
When you arrive at the encampment, you'll see reenacters, sword fighters, antique weapons experts, musicians, a blacksmith and even a surgeon living in authentic tents. These performers take their roles very seriously for your edification on maritime history and lore. And they look stunning!
Guests can watch this battle from high above in the fort, which is surrounded by a moat. That's Lily Alexander duking it out with the guys.
The encampment as seen from the second story of the fort.
These pirates didn't shop at IKEA. No electricity or Coleman lanterns here. Everything is authentic looking.
Commodore Cutter from the gulf coast has articles of piracy for little ones to sign. Both events are kid-friendly.
You can also observe the battle from ground level, but heed park ranger warnings about where it's safe to sit.
You never know who's going to win. British or pirates? Miss Felicity of the Dark Rose crew with Spike Pierce from Key West.
Captain Budd is also a fishing guide and has been sailing all his life. He was demonstrating rope and knot works. That morning, he told me, he had caught grunts from shore for an authentic Key West grits and grunts breakfast.
Left to right: Pirates of the Treasure Coast, Cannibal Chrispy, Skeleton and Pirate Louie participated in the Key West Holiday Parade.
You've seen this incredible artist's work before if you like Captain Morgan rum. Don Maitz was painting watercolors and oils on site.
The Viceroy, a member of royalty, is also a real cannon maker based out of Key Largo. I can't remember the last time I saw such an impressive "gun" from a man.
Red Beard caused quite a stir with his furry pets.
Cascabel preparing for "fire in the hole" aboard the schooner WOLF.
Hot dogs and burgers cooked over wood, pirate style. If you nosh here, order the delicious, tangy coleslaw on the side.
Captain Crudbeard of the Dark Rose crew with a beautiful African raven that says "arrrrrgh" like a pirate.
This pirate chose to swan dive off the plank.
Michelle Murillo and her performing partner Joe Catalano taught the audience what it was like to live on a pirate ship in an interactive presentation just before the battle.
More photos on Flickr
Trail of the Pirates doesn’t really end here. I made many new pirate friends and will be exploring the gulf coast of Florida next year and hopefully the east coast of the United States north of Florida – the Beaufort invasion in North Carolina beckons!
IF YOU GO
Pirates in Paradise and the Fort Taylor Pyrate Invasion typically take place the first weekend of December. Reserve your hotel early.
As if I needed to give you yet another reason to visit the beautiful Florida Keys, I can’t think of a better time to explore Key West than when the pirates are in town. You can enjoy all the wanton and lazy pleasures of this southernmost city and learn a thing or two about pirates.
Make a day of it. Explore both festivals. Sail on the flagship schooner WOLF with Admiral Finbar of the Conch Republic and musical, gunpowder-firing pirates. Bring a picnic to enjoy after the battle at gorgeous Fort Zachary beach, a state park where you can swim in turquoise blue Caribbean waters.
Oh and did you know? The fort is said to be haunted by a ghost named Wendell. Learn more about preserving this precious heritage at Friends of Fort Taylor.
And don't forget to stop at the Rum Barrel on Front Street for some great pirate-y rum drinks.
Visit the updated Trail of the Pirates itinerary for a full list of experiences.
Trail of the Pirates is an on-going documentary series on Sex and the Beach and has benefited from businesses and organizations that see value in this fun way to educate readers on Caribbean and Florida history.
This segment of Trail of the Pirates was generously supported by GM Southeast (Chevy), Pat Croce and staff from The St. Augustine Pirate and Treasure Museum, Admiral Finbar of the schooner WOLF as well as the fine folks who run Pirates in Paradise and The Fort Taylor Pyrate Invasion. Special props go to Michelle Murillo, my friend and mentor in all things pirates. She reenacts the the trial of Mary Read -- the subject of an interview from last year.