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Sailing Sojourns

Prepare for Adventure! The Pirates are crafting tall ship adventures you won’t find anywhere else. First up — our pirate-themed sail in The Bahamas. Learn the pirate life, island-hop, drink rum, learn sword play, search for treasure, and become one with the real pirates of the Caribbean.


Inaugural Sail, February 3-12, 2023

ALL-INCLUSIVE

The Pirates will set forth on our inaugural sail in early 2023 and we invite you to join us. We will set sail from Nassau, The Bahamas, aboard the Liberty Clipper, a gaffe-rigged schooner, and explore the islands as the pirates did in the 18th Century. This will be an amazing sail full of authentic pirate experiences, island-hopping, and crew reenactments to bring you the real lives of the pirates of the Caribbean. Led by renowned pirate historian Rebecca Simon, Ph.D., the crew will sail across the Bahamas for a week, island hop, visit different islands, learn about the lives of pirates and how they lived, explore old pirate haunts, and become one with legendary pirates.


Tentative Itinerary

  • February 3: Fly into Nassau, check-in at the Courtyard Nassau Downtown/Junkanoo Beach, enjoy a group dinner at the nearby Tiki Bikini Hut, meet Dr. Simon, and get acquainted with your crew mates.
  • February 4: Breakfast, visit the Pirates of Nassau museum, dive into the Blackbeard’s Escape group experience, lunch at Smuggler’s, visit at least one historic fort (Forts Charlotte, Fincastle, Montagu), board the Liberty Clipper, and have dinner in Nassau.
  • February 5: Get underway on the Liberty Clipper. Learn about the different roles on pirate crews and receive your assignment! You’ll play that role onboard the entire voyage. From cook to captain, every person plays a vital role in helping the ship function. After dinner, learn about real pirates, who became pirates, and what life was really like on a pirate ship.
  • February 6: After your pirate chores, it’s Fighting Like a Pirate, Part 1! Watch demonstrations and join in with sword fighting lessons using one of the most common pirate weapons, the cutlass. In the evening, regale in tales about pirate battles, infamous pirates, and their dramatic ends.
  • February 7: Love those sea shanties? So did the pirates! Pass the time away onboard by learning and singing authentic pirate songs. Pirates also loved their stories — and hear some of the best! The after dinner chat will be all about myths and superstitions at sea.
  • February 8: Today is all about pirate food and drink. Prepare some classic pirate meals to prepare yourself for a day of pirating. Make your own bumbo, the pirate drink of choice. It’s grog, but better! Discover the joys (and horrors) of eating and drinking like a pirate at sea. After dinner, hear how crews tried to stay safe and healthy while onboard.
  • February 9: Fight Like a Pirate, Part 2! Time to engage in a battle to destroy another ship and steal booty. The captain will assign you to your fight positions. Engage a reenactment of a fight battle. After dinner, listen in about pirate persecutions, captures, trials, and public executions.
  • February 10: Today, prepare to sell your booty ashore! In teams, examine your pirate “treasure” and determine how much to try to sell it for. Make sure you distribute the money evenly based on your ranks and jobs on the ship! Don’t forget whose job is it to record all of the goods and money. After dinner, hear the tale of Pirates on the Land: Taverns, Women, and Relationships.
  • February 11: Enjoy the final full day of sailing and vote for the best Pirates of the week’s sail!
  • February 12: Return to Nassau. We will assist your disembarkation and any transportation that you need to the airport.

Scavenger Hunts and Rewards!

On many of our islands stops across The Bahamas, join in on scavenger hunts for pirate items, and compete to be the Best Pirate on the sail. The reward? Something a pirate would love — stay tuned for more details, matey!


Where Will We Sail?

The sail onboard the Liberty Clipper will begin and end in Nassau, The Bahamas. Sails generally head east and south to visit different islands each day. While the exact sail route depends on the weather and the Captain, typical destinations include Eleuthera Island and Exuma. Expect to visit a different island each day. If we are fortunate, we will visit islands where real pirates trod in the Bahamas!


What’s Included?

Your pirate adventure is all-inclusive! This includes: chartered tall ship; accommodations; all onboard meals and drinks; your host (Pirate Historian, Rebecca Simon, Ph.D.); the pre-sail hotel room, pre-sail lunch (1) and dinners (2); museum admissions and activities; your very own uniquely-designed pirate pendant to celebrate our inaugural voyage; and other surprises we’re scheming for you! Airfare to Nassau is not included.


How Much Does It Cost?

Coming soon! We’re busy working on all the details to share with you as soon as possible.


Read Dr. Simon’s book and get ready to sail!


Bookings Begin August 1, 2021!


Sign Up Now

Bookings for all Pirates will be first-come, first-serve. Only 22 lucky Pirates will share on this very special adventure. Bookings will be available beginning July 1, 2021. Those showing a willingness to serve will get preferential treatment, so sign up now and let us know you want to sail with the Pirates.


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