Pleasure Island runs about 17 miles along the southeastern North Carolina coast, varying from two miles wide at the far north to barely a half-mile in the middle. Its southeastern tip is Cape Fear itself, the headland that gives the river and the region their name. Off that point, the Frying Pan Shoals reach 30 miles into the Atlantic, fed by the long shore currents of Onslow Bay and Long Bay colliding with the river's discharge. These shoals have wrecked ships for as long as ships have come this way. The northern boundary, Carolina Beach Inlet, did not exist before 1952, when a group of Wilmington businessmen hired a dredge to cut it. Captain Skippy Winner piloted the first commercial vessel through.

After the Civil War, the river started to dry up. New Inlet, which had been the preferred route into the Cape Fear for nearly a century, was bleeding so much water out of the river that the main shipping channel to Wilmington was at risk of becoming impassable. So between 1870 and 1881, the Army Corps of Engineers built a mile-long stone dam from Zeke's Island to the southern tip of Federal Point, then extended it two more miles south. They called it The Rocks. The work cost over a million 1880s dollars, an enormous figure, and required moving stone by the trainload to a place that had no roads. The dam closed off New Inlet, restored the river's flow, and saved the port of Wilmington. The enclosed water behind it, still called The Basin, is now a kayaker's paradise.

Around 1850, Alexander and Charity Freeman, described in the records as "free colored persons" of mixed African and Native-American heritage, bought 250 acres of swampy land on the lower Federal Point Peninsula. Their son Robert Bruce Freeman, born 1832, would eventually own nearly 5,000 acres. In the early 1920s, his descendants founded an African-American beach resort called Seabreeze on family land, with an oceanfront strip they named Freeman Beach, later known as Bop City. Through the Jim Crow era, when most North Carolina beaches were closed to Black families, Seabreeze and Freeman Beach were where Black North Carolinians vacationed. Dance halls, juke joints, hotels like the Lofton and Ruth & Joe's. Then a man-made inlet in 1952 caused erosion. Hurricane Hazel in 1954 destroyed nearly every Bop City building. Desegregation in the 1960s removed the resort's reason for existing as a segregated space, and Hurricane Fran in 1996 took the last cottages. The oceanside strip survives as Freeman Park, a public beach inside Carolina Beach. What was lost was a Black community space built across generations on land Black families had owned for over a century.

Confederate Fort Fisher, the largest earthwork fortification in the Confederacy, sat at the island's southern end and fell to Union forces in January 1865 after the largest amphibious assault in American history to that point. With Fisher gone, Wilmington fell, and the war's last major supply route collapsed. The site became a National Historic Landmark in 1961, the first in North Carolina. A century after the battle, the same headland produced a different kind of fame. In 1955, Robert E. Harrill moved into an abandoned World War II bunker at the Fort Fisher end of the island and lived there for the next seventeen years. He became known as the Fort Fisher Hermit, dispensed homemade philosophy to visitors, and at one point was the second most-visited site in the state, behind only the Battleship North Carolina. He died under unclear circumstances in 1972. The bunker is still reachable by a short trail from the Fort Fisher Ranger Headquarters.

The island sits between two major estuarine reserves: Masonboro Island to the north and Zeke's Island to the south. Loggerhead sea turtles nest on the beach each summer; green, leatherback, Kemp's ridley, and hawksbill turtles turn up less often. The Pleasure Island Sea Turtle Project tracks every nest. Ospreys hunt the shallows, pelicans line the pier railings hoping for handouts, and in winter the occasional whale rolls through offshore. Sugar Loaf, a sand dune once 110 feet high and now half that, sits inside Carolina Beach State Park, the same hill Confederate troops fortified to block Union access to Wilmington.