Before the cruise ships, before the lighthouse, before the graves, Great Stirrup Cay belonged to pirates. While the British busied themselves with Nassau and the larger Bahamian islands, the smaller cays in the Berry Islands chain offered perfect cover for ships that preferred not to be found. Old nautical charts labeled the island simply "Stirrup's Cay," and documented settlement did not begin until around 1815. Structures from that era still stand. The island resurfaced during the American Civil War as a provisioning stop for Confederate blockade runners smuggling cotton to Europe, while Union warships patrolled the surrounding waters trying to intercept them. After British emancipation, the plantation on Great Stirrup was abandoned and the island fell quiet. Then, in 1935, President Franklin D. Roosevelt arrived to fish off the reefs, a detail preserved in a New York Times dispatch from April of that year. The fish were apparently worth the trip.

World War II transformed Great Stirrup Cay from a forgotten plantation island into a listening post. The United States military installed submersible cables along the ocean floor to detect enemy submarines approaching the eastern seaboard, and two "cable houses" built for this purpose still stand on the southeastern shore, swallowed by jungle but structurally intact. After the war ended, the island's strategic usefulness did not. The U.S. Air Force constructed a LORAC radio-navigation station - Long Range Accuracy - that provided precision tracking data for early Space Shuttle launches from Cape Canaveral. The facility operated for decades, eventually leased to Motorola and other contractors working out of Patrick Air Force Base in Florida. When GPS technology rendered the station obsolete, it was shut down in 1991 and the antennas, equipment, and radial arrays were stripped and removed. The concrete pads remain, along with the helipad on the island's southern end, marked by a sign that reads "Great Stirrup Cay International Airport" - an ironic touch for a facility that never handled a commercial flight.

In 1863, the Imperial Lighthouse Service erected a lighthouse on Great Stirrup Cay to guide ships through the Northwest Providence Channel. The structure stands nearly 80 feet tall, and its beam reaches more than 20 miles across open water. For years it was a manned station, tended by keepers who lived in isolation on the northernmost island of the Berry chain. Today the lighthouse is fully automated and solar powered, a self-sufficient sentinel that needs no one. It remains one of the few original structures on the island that still performs its intended function - not repurposed, not abandoned, not overgrown. Below the lighthouse, the island's rocky southern shoreline is littered with enormous concrete blocks, remnants of the military installations that came and went. Frigatebirds circle overhead, riding thermals above the rocks. Sanderlings work the tide line. The lighthouse blinks on through it all, indifferent to the cruise ships anchored offshore.

The Belcher Oil Company of Miami held claim to the northern section of Great Stirrup Cay for years, pursuing a mix of real estate speculation, oil exploration, and a possible corporate retreat that never materialized. In 1977, Norwegian Caribbean Lines leased the property from Belcher Oil, becoming the first cruise line to gain exclusive control of a private island. The company bought the island outright in 1986. What had been a pirate hideout, a blockade-runner supply stop, a submarine listening station, and a radio-navigation site became a beach day excursion. Norwegian Cruise Line expanded the facilities in 2017, adding food and drink areas, rebuilding cabanas, and widening the beaches. A two-ship pier opened in December 2025, eliminating the need for tender boats. The island next door, Little Stirrup Cay, is owned by Royal Caribbean. Two rival cruise lines, two adjacent private islands, a shared stretch of turquoise water between them, and beneath the sand, cables that once listened for German submarines.

Great Stirrup Cay is a protected marine sanctuary, and removing anything from the water is strictly prohibited. Coconut palms dominate the landscape, along with sea grape trees whose fruit darkens to purple in the tropical heat. Land crabs scuttle through the undergrowth, and lizards of several varieties bask on the warm concrete remnants of the military era. The island's climate is reliably tropical - daytime temperatures averaging around 75 degrees Fahrenheit in winter and 85 in summer, sea temperatures hovering near 80 year-round. But the real inventory of Great Stirrup Cay is not biological. It is archaeological: abandoned cable houses, military concrete, a functioning Victorian lighthouse, a helipad, graves of strangers, and the footprint of a Cold War tracking station, all layered beneath the palm fronds and cabana roofs. The cruise passengers who wade into Bertram's Cove are swimming in water named for the Royal Navy captain buried a short walk up the hill, though few of them know it.