Before Useppa Island separated from the mainland, the area was visited by
Paleo-Indians, who were present in Florida by at least 8,000 BCE. Soon after the sea level had risen enough to separate the island from the mainland, around 4500 BCE, Indians of the
Archaic period began living on the island for part of the year, primarily during the spring and summer. Oyster shells were deposited in
middens from this time. Tools made from seashells during the period from 4500 BCE to 3000 BCE show a cultural affinity with
Horr's Island to the south. The
Second Seminole War began in late 1835. Henry Crews, the U.S.
Customs officer on Josefa Island (Useppa), was killed in late March 1836, possibly by Seminoles or by Indians working at the
rancho. Crews had been at odds with the Spaniards at the fishing
rancho, believing that they were using fishing as a cover for large scale smuggling. After the death of Crews, the "Americans" living around Charlotte Harbor, which probably included Spaniards and
rancho Indians, fled to the
rancho operated by William Bunce on Passage Island in
Tampa Bay. In late 1836 the
ranchos around Charlotte Harbor, including the Caldez
rancho on Useppa, were reported to be abandoned and "largely destroyed."
Rancho Indians, including those who were married to Cubans or were half-Cuban, were gathered up by the Army and sent west to
Indian Territory. The area around Charlotte Harbor and Pine Island, including Josefa Island, remained sparsely inhabited for several decades. The U.S. Army established
Fort Casey on, renamed, Useppa Island early in 1850, but abandoned it before the end of the year. Union troops and refugee Union sympathizers occupied the island in December 1863, and mounted a small raid into Charlotte Harbor and up the
Myakka River, which resulted in some skirmishes with Confederate troops and irregulars. The troops on Useppa Island moved to
Fort Myers after it was established in January, 1864. The
Census of 1870 found two residents on the island. It was reported to be uninhabited in 1885, and to have one family in residence in 1895. The
Atlantic tarpon fishing focused Izaak Walton Club opened on Useppa Island in the early 20th century. Chicago businessman John Roach built a hotel on Useppa Island in 1896.
Barron Collier bought the island in 1911, and developed the resort, enlarging the hotel and adding tennis courts and a 9-hole golf course. Collier made the island his official residence, from which he directed his real estate empire. Collier died in 1939, and the resort was closed during
World War II. Hurricanes in 1944 and 1946 damaged the hotel, and it was torn down. The island opened again as a resort in 1946, continuing until 1960. In 1960, Useppa briefly served as a
CIA training base for
Cuban exiles in preparation for the
Bay of Pigs Invasion. ==Archaeological investigations==