According to local folklore, Captiva got its name from pirate captain José Gaspar (Gasparilla) holding his female prisoners on the island for ransom (or worse). However, the supposed existence of José Gaspar is sourced from an advertising brochure of an early 20th-century developer, and may be completely fabricated.

Around 3000 B.C., the sands of Captiva started to erode, resulting in the eventual formation of Sanibel Island. At that time, the waters of the Gulf of Mexico were eight feet lower than they are today. It is said that the first inhabitants of Captiva were the Calusa Indians, and they were described as a war-like people (“Calusa” means “fierce people”). The Calusa Indians were not particularly hospitable to outsiders and attacked any explorers who wandered into their territory. Calusa Indians built their houses on stilts without walls, and they wove palmetto leaves together to build roves (twisted strands of fibers). The Calusa Indians were not active farmers, instead fishing for their food along the coast, bays, rivers, and waterways. “The men and boys of the tribe made nets from palm tree webbing to catch mullet, pinfish, pigfish, and catfish. They used spears to catch eels and turtles. They made fish bone arrowheads to hunt for animals such as deer. The women and children learned to catch shellfish like conchs, crabs, clams, lobsters, and oysters.” The Calusa Indians used the shells on the island for utensils, jewelry, tools, weapons, and ornaments. By the late 1700s, most of the Calusa Indians had died out.

In the 19th century, an Austrian by the name of Binder (b. 1850) was traveling on a German freighter headed to New Orleans when the ship crashed and he was shipwrecked off Boca Grande. He ended up washing ashore on what has been Upper Captiva since 1921. He lived for several weeks on what the unoccupied island had to offer, built a makeshift raft, and eventually got himself to Pine Island, where he received help returning home. In 1888, due to his service in the U.S. Army, Binder became naturalized at the age of 38 and was allowed to homestead on Captiva. For 10 years he was Captiva’s first and only inhabitant. He died in 1932 and is buried in a tiny cemetery next to the Chapel by the Sea.

Today half the island is privately owned, with luxury homes making up “Millionaire’s Row” on Captiva Drive. There are roughly 500 year-round residents. Today, Captiva can be accessed by vehicle via Blind Pass Bridge, which connects Sanibel to Captiva. North Captiva is a separate island without cars and can only be accessed by boat or small plane via a grass airfield.