Skylar was in the process of getting her inherited plantation ready for sale when she discovered an old sea chest in the attic. It was full of vintage clothes, but since Skylar didn't have any use for the old clothes, she sold the sea chest to a young woman named Savannah.

Later, when Savannah emptied the chest, she discovered a false bottom containing an ornate box and some ancient documents wrapped in an oilcloth. Thinking this might be some family heirlooms, Savannah contacted Skylar to share her discovery. The small decorative chest was full of jewels and the ancient documents included a map leading to an island somewhere in the middle of the ocean. Once they found out that the sea chest apparently belonged to a famous female pirate, Skylar, Savannah and Savannah's daughter Annie decided to travel to the island. They wanted to see if the map might lead them to a pirate treasure.