Pirates in Paradise - Pirate Festival in Key West, Florida

Download the complete schedule of sailings

Schedule of Sails

Sail aboard historic vessels during your visit to Pirates in Paradise

The Topsail Schooner WOLF plays center stage for this colorful, swashbuckling festival, featuring Adventures on the High Seas.

Awash with Historic Re-Enactors bedecked in colorful Pirate garb hanging from the yardarms. Captain Finbar and the WOLF will attack unsuspecting vessels in Key West Harbor.

Sailing Schedule
Topsail Schooner WOLF will sail from her homeport of Safe Harbour Marina on Stock Island thru Thanksgiving Weekend (Thursday, Friday & Saturday, November 22, 23, 24 & 25) and then will sail from Old Town (Wed, November 28 thru Sunday, December 2.)

We strongly recommend advance reservations, as seating is limited.

Note: Some sailings fill up early, especially the sea battles with the fort. Book early!

All WOLF excursions are $50 + tax per person (children under 12 $25 + tax.)

ach day throughout the Pirates in Paradise Festival, WOLF will be offering afternoon and sunset cruises that promise to nurture the ‘inner pirate’ in kids of all ages! The WOLF will also be offering several specialty sails including a CRN SHOOT & SAIL (11/26) and LITERATURE & THE SEA SUNSET SAIL (11/29.) For more info, please call 305.296.9694 or email Info@PiratesInParadise.com.

We also offer ferry excursions to the Dry Tortugas, Deep Sea, Flats and Backwater Fishing Trips, Eco Adventures, Snorkeling, Dive Trips to the Coral Reef and Wrecks, Jet Skis and other water and air based excursions.

Throughout the rest of the year, the WOLF is available for private charters and nautical excursions of all types. The ship can travel throughout the Bahamas, Caribbean and East Coast and Gulf Coast of the US. The WOLF is currently finalizing plans for her 2012 East Coast Ambassador Voyage, which will include stops in Savannah, GA, Charleston, SC, Hampton, VA, Annapolis, MD, Boston, MA, New London, CT and New York City. We invite one and all to join us in this tall ship extravaganza that will commemorate the Bicentennial of the War of 1812.

Download our sponsor packet.

*photos by Tony Callahan, Callahan Digital Art, Mike Cuffin/Barefeet Photography, Anita Mixon, Wendy Wellman, Jan Minutti and Angelina Morgan.