Book your trip today...

Sailing Charter

The Calypso Gypsy is an 80-foot sailing yacht designed and built for charter. At the time of her building she was the largest fiberglass ketch in the World. The combination of classic lines and reliable technology makes her a remarkable vessel. She contains five spacious staterooms, four forward, a separate crew quarters aft, plus three separate heads. She may take 24 passengers overnight.

She can accommodate intimate private parties or large groups up to forty two for day charters. 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.

The Calypso Gypsy is available to charter privately. Half day, full day or overnight trips can be arranged to snorkel and explore the beautiful Florida Keys and Marquesas Islands. Extended voyages can be arranged for groups of 6 to 24 on an overnight basis.

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