The waters around Little San Salvador have a long memory for disaster. In September 1883, a Category 3 hurricane tore through the Bahamas. Captain Dorsey of the Carleton, sailing from Nassau with 14 passengers, steered into the island's harbor to wait out what he believed was a thunderstorm. By 10 pm, the barometer had fallen four tenths, and the captain informed his passengers that a hurricane was upon them. The ship was blown out of the harbor; several passengers died, including Reverend J.S.J. Higgs, the rector of San Salvador Island's parish. Two decades later, in 1901, the British sloop Lizzie Culmer wrecked on the island's shore, killing one woman. The schooner William F. Campbell, loaded with pineapples, rescued the survivors. On New Year's Day 1902, the fruit trader Frascati struck a reef just offshore and sank. Little San Salvador collected ships the way a net collects driftwood.

Franklin D. Roosevelt visited twice. In 1935, aboard John Jacob Astor IV's former yacht Nourmahal and escorted by the USS Farragut, he cruised the Bahamas on his annual fishing trip. Off Little San Salvador, the presidential party launched small boats to capture tropical fish for the tanks aboard the Nourmahal. Roosevelt returned the following March on the presidential yacht USS Potomac for swimming and fishing. In 1940, he met with Edward VIII to discuss potential sites for a new U.S. naval base in the Bahamas - Little San Salvador made the shortlist, alongside Eleuthera and Long Island. Dwight Eisenhower continued the presidential tradition in 1957, visiting to troll for fish. Between the presidents came the scientists: in 1907, Dr. Nathaniel Lord Britton, director of the New York Botanical Garden, led an expedition hoping to find new plant specimens. In 1972, a team from Boston University arrived for an ecological survey. The island kept drawing people who wanted something from it - fish, plants, strategic advantage.

The most improbable chapter in the island's history arrived in 1987. In the wake of the infamous Mobro 4000 garbage barge incident - when a load of New York trash sailed up and down the East Coast looking for a dump - someone proposed turning Little San Salvador's lagoon into a landfill, then building condominiums and restaurants on top. The Bahamas rejected the idea. The island's fortunes took a more conventional turn when Knut Kloster, founder of Norwegian Cruise Line, began negotiating to buy it in 1979. He wanted a guaranteed beach stop, "an afternoon of swimming and lazing on the beach." NCL acquired the island, and on May 30, 1980, the SS Norway became the first large cruise ship to visit. But NCL's tenure was temporary. In December 1996, Holland America Line purchased Little San Salvador for $6 million and invested $16 million in new facilities, renaming it Half Moon Cay when it opened in December 1997.

Beneath the corporate ownership lies a more tangled history. In 1863, Joshua Newbold owned one-eighth of the island. His will left his share to his wife Jane for life, then to their eight children - Edward, Joshua, Hezekiah, Dorsett, Josiah, Zephaniah, Elijah, and Georgiana - for life, and then to their children. By 1930, the Bahamas Supreme Court had to sort out who owned what, ruling that each of Joshua and Jane's children held an equal per-capita share of the original eighth. Little San Salvador, LLC began buying shares from the Newbold grandchildren, accumulating thirteen-sixteenths of the island by 1960. A competing claim surfaced in 1987 when Island Sanctuary Ltd asserted it had purchased shares from Newbold descendants back in 1966. The family that once held this distant land in trust for their children could hardly have imagined it would become a beach playground for cruise ships carrying thousands.

Today, Holland America develops just 50 of the island's 2,400 acres, maintaining the rest as wildlife habitat. Waterfowl nest on the undeveloped land. Cruise passengers arrive by tender - the island lacks deep-water docking - to find swimming, snorkeling, scuba diving, parasailing, horseback riding, and glass-bottom boat rides waiting on the developed strip. In December 2024, Carnival announced a massive expansion: a new pier to accommodate its largest Excel-class ships, reducing the need for tenders and rebranding the destination as RelaxAway, Half Moon Cay. The expansion aims to compete with Royal Caribbean's CocoCay. Whether the island's waterfowl and remaining wild acres survive the next round of construction remains an open question. Little San Salvador has weathered hurricanes, garbage proposals, and ownership disputes. A bigger pier may prove to be the most transformative challenge yet.