Captiva Island History

Captiva Island is one of our favorite places in the world. So here’s a little Captiva Island history, providing you with a bit more background on the place we love so much.

What’s in a name?

Legend has it Captiva Island was a respite for pirates in the 1800’s. One of those pirates, Jose Gaspar (also known as Gasparilla), allegedly held his female prisoners captive on the land that would become, you guessed it: Captiva Island.

Like many stories, this appears to be just another tall tale; the Gasparilla legend is more fiction than fact and the tie to Captiva’s name can only be traced back to a real estate pamphlet.

Early Captiva Island History

Captiva is located next to Sanibel Island, with the two islands connected by a short causeway. When the area formed nearly 6,000 years ago, the two islands, along with North Captiva, were believed to be one, larger island.

The Calusa people were the first known inhabitants on the islands 2,500 years ago. They used natural materials provided by the island and surrounding area, eating seafood and using leftover shells to create useful tools.

European Discovery

Spanish explorer Juan Ponce de Leon is said to have been the first European to visit Sanibel Island in 1513. Attacks from the Calusa prohibited any permanent Spanish settlement on the islands. By the close of the 18th Century, diseases such as tuberculosis, measles, and yellow fever all but wiped out the Calusa.

Spain claimed what we now know as Florida during the Age of Exploration and until the end of the Seven Years War when Britain took possession for a brief period of time. Following the Treaty of Paris in 1783, which ended the American Revolution, Florida was transferred from Britain back to Spain.

The Spanish would control Florida until 1821.

Statehood to Settlement

Florida became a territory in 1822 which lasted until it joined the union as the 27th state in 1845. It wasn’t until after the Civil War and Seminole Wars that settlement of the greater Fort Myers area began. Agriculture brought the first settlements to the island.

At one time, a key lime plantation made up the northernmost two miles of Captiva. That land is now South Seas Island Resort. Coconuts were grown at what is now Jensen’s Twin Palm Resort and Marina. Agriculture attracted residents until nature intervened.

President Theodore Roosevelt once fished in the area. His dedication to preserving nature led to the creation of the Pine Island National Wildlife Refuge in 1908. The waterway between Pine Island and Captiva is named after President Roosevelt.

Storms Define Island Geography

Hurricanes are no stranger to the area. In 1921, a hurricane hit, separating Captiva into two islands (now Captiva and North Captiva) at Redfish Pass. The 1921 storm devastated the island, causing an end to much of the agriculture on the island. Sanibel Island suffered only minimal damage. But in 1926 another storm would put an end to agriculture on that island as well.

Iconic and Historic Buildings

One of Captiva Island’s most iconic buildings is the Island Store, located at Andy Rosse Lane and Captive Drive. The building, first constructed in 1915, has seen a variety of uses and owners. Cartoonist and conservationist, J.N. Ding Darling, once owned the store and is rumored to have removed the second level, making it the iconic structure it’s known as today. In late 2020, the store reopened after a significant renovation and is now managed by Bailey’s General Store of Sanibel.

In 1924 a beachside dressing room was built just off the Gulf at the Captiva Fisherman’s Lodge. This property was purchased by the Wightman family who turned their family home into the Gulf View Inn. Vacationers know this site today as The Mucky Duck Captiva.

During the Great Depression, Price’s Cottages on Captiva Island opened for business. J.N. Ding Darling recommended a new name for the cottages that has become synonymous with Captiva Island for generations: ‘Tween Waters Inn (known today as ‘Tween Waters Island Resort & Spa). While the resort has evolved over the decades, several of the original buildings still stand today. In 2011, ‘Tween Waters became listed in the National Register of Historic Places. 

More Information

The Captiva Island Historical Society is a great resource to learn more about the island. For more in-depth background on Captiva Island and the surrounding area, check out the Sanibel Captiva Chamber of Commerce.

Capturing Captiva