Bloody Pirate

The Bloody Pirate is a beautiful schooner sailboat in the luxurious Florida Keys. She is named after the famous Code Rum cocktail drink. Enjoy an exciting Keys sailing adventure and watch us hoist her red sails on a true tall ship.. She can accommodate intimate private parties or large groups up to 38 people for day charters or 24 overnight. With her classic lines and open interior you'll feel right at home. Her professional crew will enable you enjoy a relaxing cruise or you may try a real hands-on sailing experience. She is the perfect vessel to take you to the abundance of tropical reefs in the Florida Keys to snorkel and explore. She is particularly suited to large group charters.


Calypso sailing offers a provisioning service to help get your charter off to a great start. With a little prior organization you can arrive to a vessel that is fully provisioned to your own tastes. We can provide food shopping lists, food and cocktail menus to  ensure that all your necessary and favorite items are all onboard and ready for your charter. We are happy to arrange any of your vacation essentials for you so you don't have to waste valuable vacation time shopping. 

Feel free to contact us about shipping some items to us ahead of time also we will make sure they are waiting onboard for you.

Please call for all departure times or for further information.

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