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The African Queen is available for your private event and has her own trailer if you would rather have her as a centerpiece on land at an event instead of in the water.


Dealing with large charter groups is our specialty. Whether you want to form part of the crew or just lie back and relax we can provide a trip that will appeal to the whole group. Our captains are happy to provide instruction on Navigation, hoisting the sails and general seamanship. We will also help you catch and prepare seafood as well as advise you on swim, snorkel and dive etiquette.


  • Provide email flyers that you can send to help with informing people on the nature of our charters
  • Work with you on itineraries and arrange shore time where you can visit local tourist hotspots
  • Provide menus and work with you on special food requests
  • Arrange snorkel and fishing equipment


Calypso Sailing can help organize your corporate event or party. We work closely with our clients to come up with themes and itineraries that accommodate your groups needs. We can then help plan your menus and provide beverage options. Our vessels can depart from Key West, Key Largo or Marathon in the Florida Keys and can accommodate groups from 6 to 42.

  • Make your guest and honorary Captain with Hat, Certificate and Personalized bottle of Rum or Wine
  • Menus tailored personally for your event
  • Full Bar with Cocktails, Captains Rum Punch or special requests
  • Team building/ Regattas - we will organize your group into teams that help navigate, hoist sails and drop anchor aboard our vessels


Charter one of our vessels for a Romantic Wedding. Getting married on board with the Atlantic Ocean surrounding you creates a magical experience that you and your guests will treasure forever. Our vessels can be chartered just for the ceremony or as a package with accommodations. We can help you organize everything you require from flowers, cake and delicious menus to music, photography and the actual ceremony itself to ensure your special day comes off without a glitch.