About 6,000 years ago, historians believe that Captiva Island and Sanibel Island were once connected to form one mass. Today, Sanibel rests just south of Captiva. It is believed that a tropical storm swept through the island dividing it in two about 1,000 years ago, according to Sanibel & Captiva Island Real Estate.
The Calusa Indians were the first known inhabitants of the island, having arrived nearly 2,500 years ago.They were talented laborers and turned the island's waterways into powerhouses that produced fresh vegetation and rich foods. The shells were kept and used as foundations for housing. Some of these mounds are still visible today. By the late 1700s the Calusa population vanished because of disease that was brought by the Spanish.
Juan Ponce de Leon discovered the island in May 1513. In 1926, fishermen found a large rock on Pine Island near Captiva Island that is inscribed with his name and the year 1513. According to legend, the island was explored by pirates. The island is rumored to have received its name when pirate Jose Gaspar (aka Gasparilla), held captive wealthy women for ransom.