Jamaica Homes News · Caribbean Island Guide
Cayman Islands
Zero Tax. World’s Best Diving. Caribbean’s Financial Capital.
Chapter One
Discovery
1503 — 1670s
On May 10, 1503, Christopher Columbus — blown off course on his fourth and final voyage to the Americas — sighted two small islands and named them Las Tortugas, “The Turtles,” for the vast numbers of sea turtles swarming the surrounding waters. These were Cayman Brac and Little Cayman. Grand Cayman was documented shortly after.
Unlike most Caribbean islands, the Caymans had no indigenous permanent population. The absence of native settlements meant there was nothing to draw Spanish colonists, and the islands remained largely empty for over 150 years after discovery. What they offered instead was an extraordinary abundance of marine life: turtles, fish, and fresh water from natural wells on Grand Cayman.
Pirates and privateers understood the strategic value immediately. Sir Francis Drake passed through in 1586, and the Caymans became a regular waypoint for ships crossing the Caribbean. Figures associated with Blackbeard and Sir Henry Morgan used these islands as sheltered anchorage and fresh-water sources. By the mid-1600s the islands had a rough population of mariners, woodcutters, turtle hunters, and wreckers.
Columbus found so many turtles he could barely see the water — which is why these islands are named what they are.
Historical record, 1503Chapter Two
British Settlement
1670s — 1800s
Following the 1670 Treaty of Madrid, which formalised British control of Jamaica, the Cayman Islands came under British jurisdiction as a dependency. The first permanent settlers were British soldiers, their families, and a mixture of freed Africans, shipwrecked sailors, and deserters who found refuge on the uninhabited shores.
What distinguished Cayman from every other British Caribbean colony was its economy. There was no terrain suitable for large-scale sugar cultivation. Instead, the Caymans developed around turtling — an industry in which Caymanian mariners became acknowledged masters of the Caribbean. They ranged as far as Nicaragua and Cuba, supplying turtles to Jamaica and beyond. Green sea turtle was the protein that fed plantation populations across the British Caribbean, and Caymanians controlled much of that supply chain.
A second strand was wracking — salvaging ships grounded on the treacherous reefs. The complex navigation required produced extraordinarily skilled pilots. Legend holds that King George III granted the Cayman Islands exemption from conscription and taxation in 1788 after Caymanians rescued survivors from the “Wreck of the Ten Sail.”
Caymanian turtlers were among the finest mariners in the Caribbean — they had to be. The reefs that wrecked others were their home waters.
Maritime historyChapter Three
Self-Governing Colony
1800s — 1962
In 1863, the Cayman Islands were formally annexed as a dependency of Jamaica under British colonial administration. The relationship was administrative rather than cultural — Caymanians thought of themselves as distinctly Caymanian, not Jamaican, and 150 miles of open sea reinforced that separation.
The defining feature of 19th and early 20th-century Cayman was its seafaring tradition. Denied the land wealth of larger islands, Caymanian men went to sea. By the early 1900s, Caymanian sailors crewed vessels across the globe — renowned for skill, reliability, and discipline. The “ships of shame” was a term applied in solidarity — Caymanian seamen sending remittances home that sustained their island communities.
When Jamaica moved toward independence in 1962, Caymanian leaders faced a defining choice: independence with Jamaica, or remaining British. They chose Britain — a quiet decision that, in retrospect, would prove one of the most consequential in Caribbean economic history.
When Jamaica left, Cayman stayed. It was a quiet decision that would define the next half-century.
Caymanian political historyChapter Four
Financial Revolution
1960s — 2000s
The decision to remain British opened a window of opportunity that Caymanian leaders seized with remarkable foresight. In the late 1960s, the government passed a series of laws — the Banks and Trust Companies Law (1966) and associated financial legislation — designed to attract Eurodollar deposits and offshore banking. There were no income taxes, no corporate taxes, no capital gains taxes. None at all.
The timing was perfect. The global Eurodollar market was booming. International banks needed offshore booking centres free from the growing regulatory burden of US and UK financial rules. Cayman offered confidentiality, stability, a common-law legal system, and zero taxation — a package no rival could match.
By the 1980s, the Cayman Islands had become the world’s fifth largest banking centre by assets. More than 600 banks operated from George Town. The hedge fund industry followed in the 1990s — Cayman hosted more hedge funds per capita than anywhere outside New York and London. A small island of turtle hunters and merchant seamen had become the financial infrastructure for a significant portion of the world’s capital flows.
Cayman didn’t stumble into offshore finance. It was engineered — a deliberate legal architecture built on one of history’s most elegant propositions: zero tax.
Financial historyChapter Five
Modern Cayman
2000 — Present
On September 11–12, 2004, Hurricane Ivan struck the Cayman Islands as a Category 5 storm — the most destructive hurricane in Caymanian history. Ivan damaged or destroyed 83% of properties on Grand Cayman. The rebuilding process transformed the islands: construction standards were raised dramatically, and the market that emerged was built at a higher standard and larger scale than anything before it.
Seven Mile Beach became one of the most valuable coastal real estate strips in the Caribbean. The Ritz-Carlton opened in 2005. The Grand Hyatt Seven Mile Beach opened in 2025. In 2025, residential real estate sales topped US$1 billion for the first time in Caymanian history. Q2 2026 set a single-quarter record of $412 million. Active listings reached $3.54 billion.
But success brought tensions. Construction costs are the highest in the Caribbean. Locals face a severe affordability crisis as international buyers dominate a market priced beyond the reach of most residents. The 1990s planning framework has struggled to keep pace. With 60% of the population comprising expatriates, the question of what it means to be Caymanian has grown more urgent with every record quarter.
The Cayman Islands went from Category 5 devastation to a $1 billion property market in twenty years.
Real estate analysis, 2025Economy
The Zero-Tax Financial Capital
The Cayman Islands operates one of the world’s most distinctive economic models — no income tax, no property tax, no capital gains tax — and has built a global financial services industry on that foundation while simultaneously creating the Caribbean’s most active luxury property market.
Island Life
Culture & Character
From the world’s best wall diving to the last turtle centre in the Caribbean — Caymanian culture is shaped by the sea, built by mariners, and increasingly shared with the world.
Real Estate
The Cayman Islands Property Market
No taxes on property purchase, ownership, or sale. A stable British Overseas Territory with a common-law legal system, English language, and USD currency. Caribbean’s most expensive real estate per square metre — and its fastest-growing market in 2025–26.
People
Notable Caymanians
With 60% of its population comprising expatriates, the Cayman Islands is one of the Caribbean’s most international communities. The islands have produced remarkable figures in politics, law, and tourism development — the architects of a transformation without parallel in the region.
From Jamaica Homes News
Cayman Islands in the News
Our coverage of the Cayman Islands — record property sales, the Grand Hyatt opening, the affordability crisis, and new commercial investment.
Buyer’s Guide
Frequently Asked Questions
Key questions about buying property, taxation, and living in the Cayman Islands — answered.
Explore the Caribbean
The Cayman Islands is one of our Caribbean island guides. Return to the hub for Jamaica, Barbados, and beyond.