Anguilla

Anguilla’s human story begins far earlier than the age of European sail. Archaeological evidence — shell middens, pottery shards, and ceremonial objects unearthed at sites across the island — confirms that Arawakan-speaking peoples inhabited Anguilla as early as 1300 BCE. This makes Anguilla one of the oldest continuously settled islands in the entire Caribbean archipelago, predating the pyramids of ancient Egypt’s New Kingdom. These first inhabitants were skilled fisher-farmers who navigated the Caribbean by outrigger canoe, cultivating manioc, fishing its translucent waters, and leaving behind a rich material culture now partly preserved at The Fountain, a remarkable Arawak ceremonial site on the island’s north shore.

The Arawak called their island “Malliouhana” — an Amerindian word commonly translated as “arrow-shaped sea serpent.” The name Malliouhana lives on today in one of Anguilla’s most celebrated luxury hotels — a rare instance of a modern brand genuinely honouring an ancient indigenous name rather than merely appropriating it.

Christopher Columbus, during his second voyage in 1493, is believed to have sighted Anguilla from the sea but made no record of landing. The name “Anguilla” comes from the Italian and Spanish word for “eel” — referring to the island’s long, low, flat profile visible from passing ships.

The Fountain Cavern represents the most significant Arawak ceremonial site in the Caribbean region. Deep inside the cave, a stalagmite carved into the figure of Jocahu — the supreme deity of the Taino-Arawak tradition, a god of cassava and the sea — was discovered by archaeologists in the 1970s. It is currently protected as an Anguillian national treasure.

The English established the first permanent European settlement on Anguilla in 1650, making it one of the earliest continuously occupied British colonies in the Caribbean. The colonists came primarily from St Kitts — the “Mother Colony” of the British Caribbean — and were joined by a mix of indentured Irish labourers and enslaved Africans. This founding ethnic mix — British, Irish, and African — shaped Anguillian identity in ways still visible today in surnames, in musical traditions, and in a distinct cultural resilience.

Unlike virtually every other Caribbean island of consequence, Anguilla was never successfully colonised by France or Spain. The island has no deep natural harbour suitable for large trading vessels. Its soil is thin limestone-based coral, largely unsuitable for plantation agriculture. What made Anguilla strategically worthless in the colonial era would later prove to be an extraordinary asset: its beaches, its coral reefs, and its people’s intimate relationship with the sea.

Anguilla was largely ignored by the Colonial Office in London throughout the 17th and 18th centuries. This neglect, while economically painful, fostered a strong sense of self-reliance and communal independence among Anguillians — qualities that would prove decisive in the extraordinary events of 1967. Anguillians learned early that they could not count on Britain to look after their interests; they would have to look after themselves.

If Anguilla could not grow sugar, it could harvest salt — and for much of the 18th and early 19th centuries, the island’s salt ponds were its primary source of income. The main Salt Pond and Road Salt Pond at Sandy Ground were the heart of this industry. Enslaved workers and later free labourers harvested crystallised sea salt from these shallow coastal ponds, raking it into mounds and loading it onto small vessels for export to North America, where it was used to preserve fish and meat.

Unlike the great plantation islands of Jamaica, Barbados, or Trinidad, Anguilla never developed the massive sugar estates that defined and distorted Caribbean social development for centuries. This absence of large-scale plantation agriculture is one of the most important facts about Anguillian history.

What the island lacked in plantation wealth, it compensated for in maritime culture. Anguillian boatbuilders developed a distinctive tradition of wooden racing sloops — fast, shallow-drafted, built without ballast and requiring extraordinary athleticism from their crew. These boats, known as A-Class racing sloops, became the basis of a competitive tradition that continues to this day. Anguillian boat racing, centered on the August Monday festival at Sandy Ground, is the national sport.

Fresh fish — snapper, grouper, lobster, and conch — remain the culinary heart of the island. The tradition of small-scale, independent fishing families who owned their boats and sold their catch directly gave Anguilla a social structure more akin to a community of small proprietors than the stratified plantation societies of larger Caribbean islands. This independence of spirit would prove consequential in 1967.

Slavery was abolished throughout the British Caribbean in 1834, with a transitional apprenticeship period ending in 1838 when full freedom was granted. For Anguilla, emancipation changed the legal status of the island’s African-descended population but did not transform the underlying economic realities. The colonial government showed minimal interest in providing infrastructure, education, or economic opportunity to the newly free community.

The post-emancipation period was marked by profound poverty and frustrated petitions to the British colonial authorities. Anguillians repeatedly wrote to the Colonial Office requesting improved roads, schools, medical facilities, and economic support — and were repeatedly ignored. The Colonial Office’s indifference was so thorough that when, in 1875, the British attempted to amalgamate Anguilla with St Kitts for administrative efficiency, Anguillians resisted fiercely. That anger lay dormant for nearly a century before erupting spectacularly in 1967.

In the early and mid-20th century, large numbers of Anguillian men emigrated to work in the oil refineries of Aruba and Curaçao. Others went to Trinidad. These emigrants sent remittances home, supporting families on the island and building a tradition of transnational community — Anguillian identity stretched across geography without being diluted by it.

The events of 1967 constitute one of the most remarkable episodes in Caribbean decolonisation history — a small island of 6,000 people successfully resisting the combined will of the British government and the new nation of St Kitts-Nevis, and winning. In 1967, Britain granted internal self-government to the associated state of “St Kitts-Nevis-Anguilla” — a political construct that bundled three islands with very different histories under one government based in Basseterre, St Kitts.

On May 30, 1967, Anguillians expelled the St Kitts police force stationed on the island and held a referendum on separation. The result: 1,813 votes in favour of separation from St Kitts, and just 5 against. Ronald Webster, a quiet, principled building contractor and politician, emerged as the movement’s leader and the voice of Anguillian self-determination on the world stage.

In March 1969, 35 British police officers accompanied by 315 paratroopers landed on Anguilla in what was immediately dubbed by the world’s press as the “Bay of Piglets.” The assembled force was met not by armed resistance but by Anguillian women bearing flowers and children waving and singing. The paratroopers had come prepared for combat and found a garden party.

In 1971, the Anguilla Act was passed by the British Parliament formally separating Anguilla’s political status from St Kitts. The Anguillian Revolution stands as a unique case: the only Caribbean independence movement that fought to remain under British rule.

The Anguilla Act of 1971 formally separated Anguilla from St Kitts-Nevis, and in 1980 Anguilla’s separate status as a British Overseas Territory was definitively confirmed. Anguilla is one of the very few places in the Caribbean that has actively and repeatedly chosen to remain under British sovereignty rather than pursue independence. Anguillians concluded that the benefits of remaining British — security, legal stability, currency strength, passport access — outweigh the symbolic appeal of full sovereignty.

Ronald Webster served as Chief Minister in multiple terms, joined later by Emile Gumbs, who would become the longest-serving Chief Minister in Anguilla’s history. Under these administrations, the foundations of modern Anguilla were laid: stable governance, investment in basic infrastructure, the beginnings of a luxury tourism policy, and the establishment of an offshore financial services sector.

Anguilla’s offshore finance sector — established in the 1980s and 1990s — made the island a significant international financial centre. The combination of British legal frameworks, no direct taxation, and political stability attracted offshore banking, insurance, and company registration from around the world. By the 1990s, financial services rivalled tourism as a contributor to Anguilla’s GDP.

The government made a series of deliberate policy choices: no cruise ship pier, strict building height restrictions, no casinos, and a focus on attracting ultra-high-end resort development. Cap Juluca, with its iconic white Moorish domes facing Maundays Bay, opened in 1988 and immediately established Anguilla as a seriously luxurious destination on the world stage.

The island’s 33 beaches — every single one accessible to the public, by law — are consistently ranked among the finest in the world. Shoal Bay East, a 2-kilometre arc of white coral sand framing water of extraordinary clarity and colour, appears on virtually every authoritative global beach ranking.

The luxury hotel roster that Anguilla has assembled is astonishing for an island of 18,000 people. Belmond Cap Juluca, Malliouhana (relaunched under Auberge Resorts Collection), Four Seasons Anguilla at Barnes Bay, Zemi Beach House, Kismet Anguilla, Quintessence Hotel — the island’s roster of ultra-luxury accommodation reads like a survey of the world’s finest hospitality brands. Rates at these properties can reach $3,000–$12,000 per night in peak season.

The property market places Anguilla among the most expensive real estate markets in the entire Caribbean. Luxury villas adjacent to Shoal Bay West, Cap Juluca, and Meads Bay can command $5 million to $30 million or more. International buyers — primarily from the United States, United Kingdom, Canada, and increasingly from Europe and the Middle East — are attracted by Anguilla’s political stability, British legal system, low taxation, and the sheer beauty of the island.

However, modern Anguilla faces challenges: Anguillians with Belonger status are increasingly priced out of property markets on their own island. Affordable housing is a serious policy concern. The island’s offshore financial services sector faces growing international pressure from the OECD and the EU regarding tax transparency. And the physical vulnerability of low-lying coral islands to sea-level rise and increasingly intense Caribbean hurricanes — Hurricane Irma in 2017 devastated Anguilla — makes long-term resilience planning an existential priority.