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Sailing parties, events and outings in Key West

78' Gaff Rigged Topsail Schooner

49 passengers for day charters, 20 for overnight
For a truly unforgettable experience, step aboard the only Square-Rigged, Topsail Schooner in the Historic Seaport of Key West, Florida!

  • Relive the days of old seafaring adventurers!
  • Hoist the red sails!
  • Steer the ship!
  • Fire the cannon!
  • Sail back in time and cruise the emerald green waters of the fabulous Florida Keys

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Have an adventure on the only square rigged, topsail Schooner sailing out of the Historic Seaport of Key West. Eighty feet long and able to hold 49 day passengers or 20 overnight passengers, sailing schooner is available for any of your Key West sailing needs, whether it’s a romantic sunset sail, a snorkeling adventure to the Dry Tortugas, or a wedding to remember on the beautiful waters of the Florida Keys.

Your ship features plenty of seating, amazing crew, and of course our signature red sails. Ignite your passion for sailing and for life on board this traditional sailing ship, and experience the best in Key West sailing adventure and romance.

Bring your own food and drinks, and let us transport you to a time when sailors were one with the ocean. Join the crew and hoist the sails, or just sit back, relax and take in the experience. Revel in the moment as our magnificent red sails capture the wind and the Rover sails off to a place time forgot.

While we’re sailing, be on the look out for all the amazing Key West attractions and wildlife. See dolphins, turtles, and man o’ war jelly fish as we sail near Fort Zachary Taylor, picturesque Sunset Key, and the world famous Christmas Tree Island from the decks of the pride of Key West sailing ships, then watch, wave and smile as other vessels sail in close to give their passengers a glimpse of our magnificent sailing ship with it’s distinctive red sails and tall square rig.We'll pass by famous Mallory Square under full sail.

Finally, as you sail into the glorious Key West sunset, scan the horizon for the world renowned Key West Green Flash!

A Pirate’s Life for Me!
Find your inner pirate while sailing the emerald waters of Key West. Join the crew and show your muscle hoisting the sails! Grab the wheel and prove your salt steering the ship! Let your intrepid spirit shine and fire the cannons!

Built as a mercenary vessel, our schooner sails back in time to capture the bygone days of a highly romanticized, infamous period in Key West sailing history when merchant ships, smugglers, and pirates plied the very waters we sail today.

Experience the excitement and anticipation of a real life sailing adventure as the crew trains the cannons and prepares for a broadside cannon fire exchange with a rival tall ship!

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