Pirates in Paradise
Key West, FL -Created for pirate and seafaring aficionados of all ages, the festival commemorates Key West's colorful maritime heritage. The island city was settled as a salvaging outpost in the early 1800s, and later became home to seafarers ranging from 19th-century fishermen to rumrunners to modern-day shipwreck salvors.

Top-name quality entertainment and historic re-enactors, improvisational actors, and combative stunt men from around the country will invade Key West. As you stroll the streets of Old Town and visit Fort Zachary Taylor during the Festival, don't be surprised if you run into the likes of Anne Bonny, Cascabel, Sir Henry Morgan, The Pirates of the Coast and other nefarious Brethren of the Coast.
Each day the public can join Captain Finbar and his scurvy crew of pirates aboard the schooner Wolf for Tall Ship Sails and Pirate Attacks. Docked at the Historic Seaport, the Wolf, Flagship of the Conch Republic will be offering afternoon and sunset sails. The schooner Liberty will also be offering sails during the Pirate Fest with His Majesty's Redcoats on board and the Jolly Rover will also be taking passengers on pirate sails.
Once again Fort Zachary Taylor will be the location for the Village Thieve's Market and Pirate Fest which gives us all the chance to live a pirate's life with living history encampments inside the fort itself. Pirates will be repelling invaders along the ramparts while vendors sell wares in the makeshift town. Occasional fights are bound to break out as braggarts solve their disagreements with swords and daggers in true piratical style; and various pirate entertainers add to the festive nature that fills the township. The historic reenactment of the Pirate Trial of Anne Bonny and Mary Read, based on the original transcripts of the trial, as found in Tamara Eastman's book, will be held on Saturday morning inside the fort at 11 a.m.
One of the highlights of this year's festival will be the Pirate Tavern in the fort itself, which will be open afternoon/evening on Friday, Saturday and Sunday, Dec. 5- 7. There, you'll hear tall tales and spirited chanteys while downing a pounder of ale or some sweet honey mead. It'll seem so real to you that you'll be sure you've been transported back some 350 years to the time when pirates ruled the Caribbean.
The community of Key West will once again gather to celebrate the Official End of America's Hurricane Season Party at the USS MOHAWK CGC (WPG-78) Memorial Museum's Truaman Annex Pier. Festivities begin with the Walk the Plank National Championships aboard the Schooner WOLF and will be followed with a special ceremony featuring NOAA's weather forecaster Matt Strahan and his weather crew who will ceremonially burn the Hurricane Flags, signifying the end of this year's Hurricane Season. The party continues with the Conch Republic Shipwreck Pirate's Ball which features the big band sounds of Mike Emerson and the Southernmost Brass Band, with special guest, Queen of Swing Norma Miller.
For those aspiring writers and artists wishing to get their inspiration from the sea, the Festival's annual Artists', Historians' and Authors' Sail and the Literature & the Sea Caribbean Pirate's Buffet at El Meson de Pepe on Mallory Square will feature participating artists, historians and literary luminaries include Janny Wurts, Don Maitz, Carol Shaughnessy, Cynthia Zeuli and "Queen of Swing" Norma Miller (who will be celebrating her 89th B-day during the festival.)
Looking for lodging accommodations and reservations for our nautical excursions? We can help. Just give us a call at 305-296-9694
For festival highlights and a schedule
of events Click Here.
For the most recent info on this event and others,
check our Key West Special Event Calendar.
















