Calypso Sailing | Florida Yacht Charters | Key West Sailboat Charter. Calypso Sailing was established in 1988 with locations in both Key Largo and Key West that specialize in luxury sailing vacations on Leopard catamarans. Calypso Sailing charters day, sunset and overnight sailing adventures in the Florida Keys.. Florida Yacht Charters,Sunset Cruise Key Largo,Key West Sailing Charters,Sailboat Charter Key West,Sailing Charters Key West,Sailboat Charter Flordia Keys,Key West Sailboat Charter,Catamaran Rentals Florida Keys,Catamaran Rentals Florida,Florida Catamaran Charter,Florida Keys Sailing Charters,Key Largo Sunset Cruise,Bareboat Charter Florida,Catamaran Charters Florida,Bareboat Charter Florida,Key West Boat Charters,Key Largo Snorkeling