Currently, American Airlines regional subsidiary American Eagle is the only jet operator flying from Anguilla, and they use small Embraer E175s. And even that has a quirk.
According to Vince Cate, who has lived on the island since 1994 and has run the .ai project since the beginning, direct flights that travel from Anguilla to Miami can’t take off fully loaded with both people and fuel because the runway is not long enough. When the flight is full, the plane has to stop in Antigua, refuel, and then fly to Miami. “It’s annoying,” Cate chuckled.
The primary goal of lengthening the runway is to bring in big planes and direct flights from major international airports.
“I am really looking forward to the direct flights in from places like NYC,” says Rob Willsher, owner of the Anguilla dive shop Vigilante Divers. “Getting to Anguilla can be a challenge and puts people off.”

Source: Christoph Pradel, The Anguilla Tourist Board
Willsher, a British military veteran and part-time officer in the Royal Anguilla Police Force Marine Unit, also thinks it will be helpful for those locals who live on Anguilla; he isn’t worried about more people changing the vibe of the island.
“I do not think that the airlift will ruin the character or charm of Anguilla. We need tourism, it is all we have,” says Willsher.
Change Is Hard
But not everyone is onboard. While the island’s government is looking for growth, among some of its most vocal critics are members of Anguilla’s sizable expat community who fear that the rush towards progress may come at the cost of Anguilla’s coveted hidden gem status.
Plans to expand the runway for larger planes have been met with pockets of resistance.
“Bringing in bigger jets and more tourists will change [Anguilla’s] character completely,” said one expat and property owner who spoke with Skift on the condition of anonymity because they do not agree with the government.
“It will no longer be the peaceful retreat that people, including myself, fell in love with. Anguilla needs to be kept as an upscale, limited destination, not become Jamaica or the Dominican Republic. The day Anguilla gets jet skis and casinos is the day I sell my house.”

Government officials acknowledge the tension. “There is a balance between economic opportunities and maintaining our unique charm,” says Minister Kentish-Rogers, also noting that Anguilla’s structural factors naturally limit large-scale tourism expansions. In other words, with hotel occupancy currently only hovering around 50%, the island has space for approximately double the travelers in its existing hotels.
Anguilla’s tourism ministry echoed this. “Anguilla has a very niche type of tourism. We don’t do cruise ships, casinos, or fast food joints,” says Hughes. “The folks who are really concerned are those who have been coming to Anguilla for 40 years. They didn’t like it when we got electricity or street lights. But we want nice things too — paved roads, educational opportunities, good healthcare.”
‘Keep Taxing the Rich Tourists’
Also at issue: taxes. For an island that has historically been a tax haven, the introduction of the 13% goods and services tax last year fueled public outcry. And with an election on the horizon in 2025, tensions are mounting.
“The government is rolling in money,” one resident said, pointing to the .ai funds. “Why are they taking money out of the maid’s wage, where she’s earning $6 an hour? It doesn’t seem fair to be taking it from somebody who’s just scraping by.”
An expat echoed the sentiment: “People are struggling with basic expenses, and yet, there’s this huge influx of money from .ai that isn’t being transparently accounted for. The locals feel completely duped.”
The frustration is especially evident at Elvis’s Beach Bar, a beloved local haunt and cornerstone of the island’s social scene. “We have yet to see any accounting of these AI funds,” said owner Brett Fetterolf, capturing the mood of many. “We have no idea where the funds have gone or are going.”
Still, some unity remains on one issue – continuing to tax the tourists. “Tourists are spending $2,000 a night on the hotel room. Keep taxing the rich tourists. We’re fine with that,” a resident added.
Amid the financial controversy, Hughes pointed to recent efforts in public welfare. “Last year, we embarked on providing free, comprehensive healthcare for those over the age of 70. Now, we are looking to expand it to include diabetics, the handicapped, and potentially lowering the age threshold,” he said, positioning the windfall as a path toward greater social benefits.
Until the Next Fad
Webster says some of the major tech power players have come to Anguilla and offered to buy the rights to the .ai domain outright. The answer for now is ‘no’. “We see the potential for it for Anguilla,” says Webster. “We’re putting all the building blocks in place.”
“We aim for wholesale changes,” Kentish-Rogers explains. “Our goal is to ensure that everyone feels the net benefit of these funds.”
Webster wants to make Anguilla an AI technical hub, filled with companies and people who are working in the field of machine learning.
“We have good weather. Sun, sand and sea. And hospitable people,” Webster says. The ultimate goal is to further diversify the economy. Anguilla has already opened up a special economic zone so companies can register virtually and offer low or no tax incentives.
“We’re thanking God that back in 1985 when the internet came and the world started giving these codes to different countries that we got .ai,” Webster said with a smile. He wants to make Anguilla an artificial intelligence hub in the Caribbean and turn the island’s good luck into a working economic engine that serves Anguillians well into the future.
“We see the potential for it for Anguilla,” Webster says. “We want to have a continuous revenue stream until some other fad comes along.”
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Publish date : 2024-12-22 01:00:00
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