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The privateer Captain Leatherwing and his trusty first mate Alfredo board a Spanish ship known as the Santa Corazon. Leatherwing captures the crew and rescues the island slave girl Princess Quext'chala. Sailing back towards the Cayman Islands, Leatherwing's vessel the Flying Fox stops at Kingston Harbor. A street urchin known as Robin Redblade stows away on Leatherwing's ship.
Meanwhile, a rival pirate captain known as the Laughing Man attempts to find Leatherwing's hidden harbor, Vespertilio Cay, also known as the Bat's Cay. The Laughing Man scuttles a ship and interrogates its captain as to the Bat Cay's location.
The Flying Fox brings Princess Quext'chala back to her father King Hapa. To show his gratitude, Hapa offers Leatherwing his daughter's hand in marriage. Leatherwing accidentally accepts a ceremonial marriage bracelet before realizing the full ramifications of receiving such a gift. Leatherwing and Alfredo board the Flying Fox and sail off. Leatherwing discovers Robin Redblade's presence on his ship and provides him with food and a cabin.
Meanwhile, the Laughing Man finds a vivacious female pirate named Capitan Felina. The two conspire with one another to find Bat's Cay. The Laughing Man pretends to force Felina off the plank into a sea of hungry sharks. As the Flying Fox approaches, Leatherwing sees what is taking place and dives into the water to save Felina. He brings her aboard his ship and becomes immediately infatuated with her. Felina is discouraged however as Alfredo indicates that his captain only recently took a bride. With Felina on board, Leatherwing sails for Bat's Cay.
The Laughing Man follows in his own ship the Pescador. He enters Bat's Cay and fires his cannons at the Flying Fox. Capitan Felina decides to betray the Laughing Man and takes Leatherwing's side in the fight. Leatherwing boards the Pescador and delivers a fatal stab to the Laughing Man's chest with his sword. He then professes his love to Capitan Felina.
Some time later, Admiral Cobblepo ambushed the Catspaw, Capitana Felina's ship, taking her and Robin prisoners, Robin sent a carrier bird with the message for Leatherwing, who then attacked Cobblepot's ship with the Flying Fox. The defeated admiral was dropped in a longboat which ended at the South Pole. Admiral Cobblepot was never seen again.