07/14/2026
There is a mangrove island in Pine Island Sound, a mile long and reachable only by boat, that has been, in order: a shell-mound fishing camp, a Cuban smuggling station, a Union outpost, a fishing club for some of the richest men in America, a secret CIA base, and a private club for the wealthy. All of it happened on one square mile of ground called Useppa. Boats pass it every day with no idea what happened there.
This is the story of a single mile of ground that kept ending one life and starting another. It lies just north of Naples, and one of the men who eventually called it home gave his name to Collier County.
TEN THOUSAND YEARS
Useppa was not always an island. During the last ice age the sea around Florida sat a hundred feet lower than it does now, and Useppa was high ground on the mainland, a set of old stabilized sand dunes. Paleo-Indians were moving through the area by around 8000 BCE. The sea rose and cut the high ground off from the mainland around 4500 BCE, and soon after that people began coming out to it by water, mostly in spring and summer, to fish and gather shellfish. They left their oyster shells behind in heaps.
Those heaps are still there. A conical shell mound about thirty feet tall stands near the south end of the island, built one meal at a time over thousands of years. This is the country of the Calusa, the people who ruled Southwest Florida from towns they raised out of shell, with the capital at Mound Key across the water. Useppa sat inside their world as a seasonal camp and a place to work shell into tools. Occupation ran on and off until about 1200, then trailed away. The island holds enough of this deep past that it was placed on the National Register of Historic Places in 1996 for its archaeology alone. A pair of ancient burials found on the island were reconstructed into faces the museum now calls Useppa Man and Useppa Woman.
THE RANCHO
The next people to settle in came from Cuba. Around 1784 a Cuban fisherman named Jose Caldez set up a seasonal rancho on Useppa, a fishing station where crews caught mullet along the coast and salted and dried it to ship to Havana. Caldez hired both Cuban and Native American workers, and by the 1830s the rancho had grown to nearly twenty palmetto-thatched houses and about sixty people. Men from the rancho married local women, and some of their children were sent to Cuba to be baptized.
The island carried Caldez's mark in its name. Through the early 1800s it was known as Caldez Island, and as Josefa, after the schooner he sailed. The name Useppa did not appear on a chart until 1855, and it is most likely just Josefa worn down by time and English-speaking tongues.
The rancho did not end quietly. A U.S. customs officer stationed on the island, Henry Crews, suspected the fishing trade there was cover for large-scale smuggling. Crews was killed in 1836, around the start of the Second Seminole War, and the fishing stations around Charlotte Harbor emptied out soon after.
THE PIRATE THAT WASN'T
There is a more famous version of how the island got its name, and it is worth telling because so many people believe it. The story goes that the pirate Jose Gaspar, Gasparilla, captured a Spanish noblewoman named Josefa, fell for her, and killed her in a rage when she refused him, then buried her on the island in remorse, so that Josefa's Island became Useppa.
It is a good story, and it is not true. Historians have found no record of it, and the pirate Gaspar himself may never have existed. The tale has done real harm over the years, used to sell fake treasure maps and to justify illegal digging into the island's Native American burial sites. The plainer explanation, Caldez and his schooner, is the one the record supports. Gar Beckstead, who owned Useppa for decades and did not believe the legend either, still gave his first daughter the middle name Joseffa.
THE UNION ISLAND
Florida seceded with the Confederacy, but Useppa spent the Civil War on the other side. The U.S. Army had built a small post called Fort Casey on the island in 1850 and abandoned it within the year. When the war came, local men who stayed loyal to the Union took refuge on Useppa and the islands around it, out of reach of the Confederate mainland.
They did not sit still. They guided Union ships through the shallow passes of Pine Island Sound, where the Navy was blockading the coast to choke off cattle shipments to the Confederate army. They took part in capturing Confederate supply vessels, and in 1864 they were organized into the 2nd Florida Cavalry, a Union regiment raised in a rebel state, which helped take Fort Myers. For a few years a rebel state's coast had a small, stubborn pocket of Union fighters working out of a mangrove island.
THE SILVER KING
In the 1880s, sporting magazines up north started running stories about the tarpon of Pine Island Sound, the silver king, a fish that could run six feet and jump like nothing a northern angler had ever hooked. Wealthy sportsmen began coming south to chase it, and Useppa sat in the middle of the best water.
A Chicago streetcar magnate named John Roach bought the island in the 1890s, by the Useppa museum's account in 1894, and built a winter home that he expanded into a twenty-room lodge, the Useppa Inn. In 1906 a room with a bath, all your meals, and a tow for your fishing skiff out to the pass ran three dollars and fifty cents a day. Men fished in three-piece suits.
Then in 1911 Barron Collier bought the island for a hundred thousand dollars. Collier was a New York advertising magnate on his way to becoming the largest private landowner in Florida, and the man Collier County would be named for, and he made Useppa his Florida home. He enlarged the inn until it held seventy-one rooms, added a nine-hole golf course, dredged sand for beaches, and turned the place into one of the most exclusive fishing clubs in the world. He named the club for Izaak Walton, the seventeenth-century author of The Compleat Angler. Its members were early in the American habit of catch and release: they let the tarpon go and kept only one scale from each fish, dried and marked with the weight, the date, and the angler's name, then hung on the club walls.
The names on those walls, and in the guest cottages, ran to the top of American wealth and fame. Theodore Roosevelt fished here. So did Herbert Hoover. The Vanderbilts, the Rockefellers, and the Rothschilds came. So did the writers Zane Grey and Mary Roberts Rinehart, and the movie stars Gloria Swanson and Shirley Temple. For a stretch of about three decades, this island a mile long was one of the most desirable addresses of the winter season.
THE SECRET BASE
Barron Collier died in 1939, and the island's glory went with him. The resort closed during the Second World War, hurricanes in 1944 and 1946 wrecked the grand inn, and it was torn down. Useppa went quiet.
Then, in 1960, it went quiet in a different way. The CIA leased the island, under the name of a Cuban businessman as cover, and turned it into an early screening and staging ground for the operation that became the Bay of Pigs. On June 2, 1960, the first ten Cuban exiles stepped off a boat onto the same dock where the Vanderbilts had once arrived for the fishing. Over that summer around seventy men passed through. They stayed in the old Collier house, by then called the Collier Inn, while the CIA ran its office out of a separate building beside it and put the barracks at the far end of the island. The island was chosen for its isolation. Reachable only by boat, it was easy to keep secret at a time when Castro had informants all through Miami's exile community.
Each recruit went through physical, intelligence, psychological, and aptitude testing, along with a lie detector examination. One CIA man said that before they were done, they knew more about these men than their own parents did. Some were trained as radio operators who memorized secret codes; some slipped into Cuba as infiltrators weeks ahead of the landing. These men became the leadership core of Brigade 2506, named for the identifying number of a recruit who died in a training accident. On April 17, 1961, roughly 1,400 of them stormed the beaches at the Bay of Pigs. The operation collapsed in three days. More than a hundred were killed and over eleven hundred were captured and held in Cuban prisons for twenty months, until the United States paid for their release in food and medicine. Veterans of the brigade have come back to Useppa over the years, walking the same low hill where they once talked about being home for Christmas.
THE ISLAND NOW
After the CIA left, Useppa passed through a run of owners. William Snow bought it in 1962 and started fixing the decaying buildings. A Tampa dairyman named Jimmy Turner bought it in 1968 and ran it for a while as an adults-only club; the sign that said so now hangs in the island museum. Mariner Properties bought it in 1973.
Then in 1976 one of the Mariner partners, Garfield Beckstead, bought the island for around two and a quarter million dollars, and this time it held. Beckstead found the place a jungle, and his first job was figuring out what to clear and what to save; he hired a horticulturist to help him tell the difference. He restored the old structures, wrote strict rules so new houses matched the old ones, and turned Useppa back into a private club. Electricity did not reach the island until 1981. Beckstead ran it until he died in 2021. He guarded its history as much as its beauty, and it was Beckstead who paid to research and preserve the archaeology and build the Barbara Sumwalt Museum that now tells the whole story.
In September 2025, for the first time in almost fifty years, the island changed hands again. A group of ten longtime homeowners, Useppa Island Partners, bought it for sixteen million dollars and began a restoration expected to run to thirty-five million, rebuilding the marina and the aging buildings. Through all of it, one building has stood the whole time. The house John Roach built and Barron Collier lived in, the house where the CIA screened the men of Brigade 2506, is still there. It is the Collier Inn, and it is being rebuilt right now, wood panel by wood panel, so that guests can once again sleep in Barron Collier's old house and eat lunch over the same water the Calusa once fished.
One square mile, reachable only by boat, has been a shell-mound camp, a smuggling station, a Union outpost, a millionaires' club, a spy base, and a private retreat. Through all of it, the land never moved. Everything else did.
