Inside the Caribbean island that’s becoming a secret AI hub
Anguilla is where high-rolling lawyers from New York go to work remotely in tranquillity. It is also becoming an unlikely world-leading beacon for AI due to one lucky coincidence. Adam Bloodworth went in search of answers
The Sunset Bar on St Maarten’s Maho Beach is one of the weirdest tourist attractions in the world. Go at any time and hundreds of cruise ship passengers will be posing with their arms in the air as jumbo jets fly metres above their heads.
The beach is right at the end of the runway, and while sunbathing is permitted, it hardly induces zen to look up at the belly of an A380 that’s close enough to see the nuts and bolts. Tour guides shout to round up their passengers back to the ships, but they cannot be heard over the jet fuel and general hysteria. In the bar, cocktails are called Liquid Viagra and women drink for free if they’re topless. Everyone’s burnt. Taylor Swift is on. Loud. There are more American retirees than there are grains of sand.
A 20 minute boat ride away from this tourist hellscape and I’m somewhere I’m sternly told to keep secret by people on the boat ride over. No one’s joking. “Leave one star reviews,” one New Yorker jokes. That secret? The island of Anguilla.
No cruise ships can get to Anguilla and there’s a ban on fast food and casinos. It is St Maarten’s snobby neighbour and that’s exactly how the expats who move here like it. There are around 15,000 Anguillans on the 16 kilometre-long island, and a small cohort of incredibly high-net-worth Americans who take the one international flight down from Miami. While loads of Caribbean islands extol the benefit of privacy, Anguilla is on another level. Brad Pitt and Jennifer Aniston escaped the paparazzi to come here for crucial break up talks, and Paul McCartney is a regular. “You hear him walking about whistling,” one local tells me. Beaches are immaculate, deserted, and chunky, for those who think bigger is better, and the sand is so fine it’ll give you an endorphin rush just thinking about running your toes through it.
Anguilla: holidays here offer another level of privacy to high-rollers and A-Listers
Lawyers on sabbatical from New York are the sorts who are drawn here – but the island’s radical change in fortunes means its demographic is set to change. Anguilla’s domain name is dot ‘AI’, a coincidence from years ago that has come up trumps for the island in light of the rise of AI. Put simply, businesses wanting a ‘.ai’ website address need to pay Anguilla for the privilege, registering their website on the island. A spike in companies purchasing new websites netted £32m in 2024 for domain name sales. “We want people to understand that AI belongs to Anguilla,” says Lanston Connor, registrar of companies on the island.
Until recently, Anguilla’s only town, The Valley, only had bumpy stone roads. Driving on them hurt the backs of drivers. Flat concrete ones have now been laid using the AI money distributed by the government, and darkened streets are now walkable at night due to new solar lighting. “The Valley feels more like a town” for the first time, one taxi driver tells me. There are still kilometres of shrubland at the centre of the island reminding that Anguilla’s development is still in its infancy: away from the handful of posh hotels, there’s not much here, and that is how the locals and esteemed guests like it.
Inside the Anguilla AI rise: the Caribbean island being revamped thanks to one lucky AI coincidence
Land at the airport and you’ll be met by walls of builders constructing a huge new terminal; drive out of the carpark and you can see a Kardashian-style villa with blackened glass windows, a new private jet airport set to open this spring, anticipating a huge rise in digital nomad and leisure visitors. In front of the new airport, a billboard displaying a picture of a perfect palm fronded beach reads: “Anguilla: The Home of AI.” Three new hotels and a marina are also in construction. It’s an arresting if perplexing new vision of a tech utopia. Could this really be the new home of AI? And what does that even mean?
During my visit, I meet tourist board reps who say the government wants to “grow, grow, grow” its visitor footprint. Others attend conferences in Asia and the Americas to promote Anguilla’s AI identity, although no one seems to know the specifics. When I ask what they are promoting, they say strategy meetings are ongoing.
There is a paradox in growing paradise: you risk ruining the DNA of the place. Isn’t Anguilla’s whole thing that it is totally empty? “The high rollers will leave,” says one Manhattan solicitor when I ask about the influx. Enjoying the remoteness as a contrast to the city, he joins court proceedings digitally from the beach during the weeks he spends working from his condo. He says on a typical day he speaks to no one, and that’s how he likes it.
On a mission to meet Anguillans, I end up on a hike with Boston, who leads walks through the arid heart of the island, showing visitors some of the 100 indigenous plants, including one that foams into a natural soap, and Candlewood that burns when wet. An essential when he was growing up in the 1960s and 70s when electricity was scarce, his hunter-gatherer approach was the only way. As a child, he’d collect Candlewood for his parents, “especially in the morning when they were baking, they needed to have that fire going if it was raining.”
He says the younger generation are reengaging with the island’s biodiversity, which seems partly down to suspicion of modern medicine and partly because of food cost hikes. Despite the little fishing boats pointed out by tourist board representatives, the island imports most of its food and with Trump, tariffs are going up. “A lot of young people are into the natural way, how we used to be a long time ago,” says Boston. How come? “They see the results of it,” he says. “We pass it on, we learn from our parents, those who were here before us.”
Later I meet Sam, the barman at the Tranquility Beach Anguilla hotel on the island’s West End, who makes a killer rum punch. He uses fresh ginger and mint from his own herb garden, fresh lime juice and a little bit of cane sugar. Tranquility Beach lives up to its name, featuring a series of privately owned condos that are rented out to guests, each with a private hot tub, most with sea views. The beach never has more than three or four groups on it, so they don’t have to wait long on their sunloungers for their rum punch. Like Boston, Sam is of an advancing age, and defaults to nostalgic reflections of Anguilla pre-tourism in the 70s and 80s, when much of the island was off-grid. No locals care about the beach: he tells me the only times he swam as a child was when it rained, when he’d play in the sea.
What do they think of AI? Boston says he doesn’t know too much about it. “I heard about it but I’m not too much into it. The year before last I listened to a programme with this guy who developed it. I listened a bit, but I still ain’t into it.”
Other locals share a similar sentiment, but Lanston Connor is trying to change that. He’s registrar of commercial activities at the Anguilla Commercial Registry, which provides financial services to national and international businesses, so he’s tasked with enticing entrepreneurs to Anguilla to buy AI domain names and – ideally – to register their companies here to exploit the tax free business privileges. “Locals are not as aware of the prevalence of the domain name as they should be,” says Connor. “And the fact that they themselves can become speculators, buy the domain and have it for reselling.”
We’re speaking from a fintech conference being held in an air-conditioned tent on the grounds of the Aurora Hotel, which has a family waterpark in its backyard, featuring loads of multi-coloured slides. At the event, local government officials are miced up so they can be heard over the hum of the AC unit. On the agenda, the usual threat of money laundering, but also AI.
We’re very disconnected to most of the Caribbean. We’re drifters and people of the sea, fishermen, hard working people
“Anguilla is an international financial centre,” says Connor. “We have no corporate taxes, we are a well regulated British overseas territory with that same credible regulation. We’re established in the financial services industry. People can [register] their company anywhere in the world, so we’re just one of many choices, but with the package we’re hoping to put together, including inviting you to visit the island, we’re hoping we can attract high net worth individuals and really high quality companies, including AI start ups. We’re trying to become the home of AI.”
Buy the domain from Anguilla – as Connor says, “it’s ours, it’s unique” – and once you’re registered, the country is preparing a whole lifestyle for you. “We’re hoping they’re already satisfied with their domain and may look to see what other AI services you can have. We have a lovely location with beautiful beaches, beautiful hotels, very nice people, and a very low crime rate. Anguilla is a paradise so we’re just trying to make it a complete paradise, one that includes all the financial services necessary for high net worth individuals to come and live and flourish and feel good. The hope is AI continues to grow, becomes a sustainable revenue generator for the government and we can piggy back on other services, other attractions.”
There is a worry that the money being made – $30 million in 2023, with $100 million projected for 2024 – isn’t reaching people like Boston and Sam. I meet one teacher who asks to remain anonymous. They tell me they’ve seen social issues getting worse due to a lack of funding in education. “There’s a lot of social decline, a decline in values, morals,” they say. “We need more counsellors at the school, we have a lot of social issues – we need programmes for that.” The government says they have been funding local schools, including new campuses, but “what they say and what they do are not necessarily the same. We don’t hear much about where it goes. I’ve seen a lot of children struggling with mental health issues.”
Sleep is a huge part of life in Anguilla – its an attractive prospect for stressed NYC lawyers
Sleep is a big thing in Anguilla – overworked lawyers down from NYC presumably hope a little of that low-stress way of life will rub off on them. Many locals work until 5pm, go to bed, then wake up at 9pm to shower before going back to sleep. That’s not just for oldies; Gen Z schoolkids admit this is the way things go here.
Pride is also big. One hope is that the AI money means Anguilla can stop taking handouts from the British government. The island is still an overseas British territory, despite how increasingly uncomfortable that feels (one of the island’s former plantations is currently being renovated into a museum; locals say it is a “good question” when I ask whether it will educate about how Britons enslaved Anguillans). “We have to pay our way,” Boston tells me, “not just wait on handouts.”
We’d finished our walk, passing an inland lagoon and ending on a gorgeous, empty beach. There are so many, you’ll easily find a whole one for yourself, but even at the hotels in peak season, sunloungers are only a third full. Metres in front of me there’s a decapitated shark’s head; Boston tells me it’s been mauled by a bird.
Bankie Banx, a local reggae singer known as the ‘Anguillan Bob Dylan’, and has laid down tracks with the folk icon, echoes Boston’s sentiment. “We’re very disconnected to most of the Caribbean, we had to survive via our wits and our minds,” he says. “Most of the people are drifters and people of the sea, fishermen, hard working people. They plant crops to keep themselves alive. People built 100 foot boats and pulled them down manually, just like the Egyptians. We’ve been that way for years.”
National pride has led to disappointment at the way the government has handled things. The Anguillan government leased the management of the AI domain to US company Identity Digital, who are operating on a revenue share. The firm is reportedly taking 10 per cent of profits from every domain name sale, with the rest going to the Anguillan government. Patrique, the head chef at the Serenity Beach hotel on the north-east coast (most of the hotels are in the more touristic West End) hoped Anguilla would keep autonomy over the management of their AI domain. “It’s disappointing,” he says from an open kitchen looking out to snorkellers and people lazing over long, late lunches of conch salad and lobster. “We have all that money but I don’t really see where it’s going. I would like it to go into the community, the schools, the future generation.”
An election in February heralded a new era. The Anguilla United Front, promising to reduce tax hikes instated in 2020, were voted in, pushing out the Anguilla Progressive Movement. Their mission, they say, is to put people first. How much of the AI money will be seen by the average Anguillan remains to be seen, but what is a near certainty is that an impending increase in flights will raise the international profile of these beguiling little stretches of sand. Visit right now – don’t leave it too long – and you’re fairly certain to be the only Brit for miles.
Visit Anguilla yourself
Go to ivisitanguilla.com. Flights from Heathrow to St Maarten via Paris or Amsterdam are bookable through airfrance.com or klm.com. Take a Calypso Charters boat from St Maarten to Anguilla with calypsochartersanguilla.com; Tranquility Beach Anguilla rooms are from $490 per night and Zemi Beach House has rooms from $625 per night; tranquilitybeachanguilla.com and zemibeach.com
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