While her early years are undocumented, it is widely accepted that Calypso Jayne bounced around the thousands of islands in the Caribbean, never settling on a permanent home. Like her mother, she was notoriously stunning, permitting only the finest European silks to accentuate her olive skin. As a child, Jayne would request shipments of garments from all over the world be delivered to her so that she and her sister could create a unique wardrobe that became the envy of the entire Caribbean.

At thirteen, Calypso Jayne decided that she needed to pursue other adventures at sea, and would no longer proceed in following her mother’s footsteps. Jayne established herself as a strong, independent teenager and quickly established close relationships with other young women who would become her crew of all-female Pirates.

Specific details surrounding Calypso’s romantic life have alluded historians but rumors suggest that only a few lucky souls have ever been graced with admittance into her private quarters.

Calypso and her gang of all-female Pirates established a brutal strategy to satisfy their need for plunder and fame. Whenever a storm passed through the area, her crew would dress their ship as though it had been ravaged by the rough seas and would plead for aid from nearby ships. When the unsuspecting sailors attempted to assist, Jayne and her crew would board the ships, rob all valuables and murder the sailors. These notorious Pirates were able to amass a great deal of wealth which allowed Jayne and her friends to enjoy a lavish lifestyle. Calypso Jayne’s reputation quickly grew as the Siren of the Caribbean.

The plunder and pillaging continued throughout the Caribbean for nearly three decades and Calypso was never caught. There are rumors that Jayne and her crew were captured by a powerful Costa Rican Pirate who she tried to swindle but no hard evidence of this theory exits. Others swear that after a rough storm Calypso Jayne still appears and lures unsuspecting sailors to their final voyage.