The strategic location of the Sea Islands is reflected in the history of conflict in the region. Port Royal Sound is the deepest and most accessible harbor on the east coast south of Chesapeake Bay; consequently, Spanish, French, and English colonizers all competed for control of the area. Fierce resistance by the indigenous Yemassee peoples made stable European settlement on the southernmost islands impossible until the early eighteenth century. Early British planters came from Barbados, bringing with them a plantation system based on monocrop agriculture and African slavery. The original cash crop, indigo, was replaced by long-staple cotton after the American Revolution. This Sea Island cotton produced huge fortunes for the White planters and the region developed a reputation for wealth and luxury.
All this came to an end on November 6, 1861, when the federal fleet, moving north to blockade Charleston, attacked the two small Confederate forts on Hilton Head. The planters evacuated inland, leaving behind their slaves and the year's cotton crop still in the field. This constellation of events set the stage for the famous "Sea Island Experiment" (or Port Royal Experiment), a federal program to determine whether or not ex-slaves could function as free, small-holding citizens. The experiment, sponsored by the secretary of the treasury and administered by a young abolitionist lawyer from Boston, envisioned freed slaves working for wages on government-owned cotton plantations while being prepared for eventual citizenship. Missionaries, teachers, and agricultural specialists were provided by northern benevolent societies, bringing an influx of young, well-educated, fiercely abolitionist men and women from the North behind the battle lines of the Civil War. As the Reconstruction promise of "40 acres and a mule" was revealed as a myth throughout the rest of the South, Sea Islanders, working with northern advisers, managed to gain legal title to most of the land they had formerly worked as slaves. In the words of Willie Lee Rose, the Sea Island Experiment was indeed a "rehearsal for reconstruction" and one of the few places in the South where African Americans emerged from the war with a secure land base.
Although many researchers have stressed the physical isolation of the Sea Islands and imply that their people have been "cut off" since the nineteenth century from mainland U.S. history, this is clearly not the case. In actuality, the islands have never been fully self-sufficient, and periodic male labor migration has been an important source of income since boll weevil infestations at the turn of the century destroyed small-holder cotton production. Sea Islanders have historically produced and sold agricultural products in the markets of cities like Savannah and Charleston, and the men have worked as commercial fishermen and longshoremen up and down the eastern seaboard for generations. What is unique to the island communities is not their geographic isolation but their economic and cultural autonomy. The ownership of land appears to be the crucial variable in Sea Islanders' ability to choose what off-island work they will accept and for how long. Many of the islands instituted their own legal and criminal codes, administered through the churches, allowing them to bypass the White-controlled "unjust law" of the mainland. Since the 1950s, much of the traditional land base has been eroded by out-migration, rising property taxes, forced sheriff's sales, and other coercive practices employed by White developers. As a result, the remaining African American population is increasingly dependent upon wages earned in the service sector of the seasonal tourist economy.