Flat tax programs in the Caribbean.

A flat annual tax is the cleanest tax story available to a globally mobile family. One figure, agreed in advance, in place of the entire apparatus of assessment — no filing built around worldwide income, no annual negotiation over what a portfolio is worth, no disclosure games played against a moving target. You know what the year costs before it begins, and so does the jurisdiction.

That is the regional promise, and this page maps who offers it. Anguilla anchors the top of the ladder; Antigua & Barbuda sits quietly in the middle; Roatán opens the bottom; Barbados runs a related but different logic. I work across all of them, and the answer is usually decided by scale rather than preference — at some income levels I will tell you the fee costs more than it saves.

Anguilla's High-Value Resident program is the arrangement the rest of the region is measured against. An approved applicant pays a flat annual tax of US $75,000, holds a qualifying property of US $400,000 or more, and keeps to a minimum presence requirement of 45 days a year on the island. Because Anguilla levies no income, capital-gains, wealth or inheritance tax, nothing is ever computed against earnings — the flat fee is the entire predictable cost of tax residency in a British Overseas Territory.

The work sits in two places: an application file — identity, source of funds, the property — prepared with the care of a private-banking onboarding, and a clean exit from your current tax system, where days, ties and timing decide whether the new residence actually holds. Dan runs both sides alongside island counsel and your home-country advisors.

The arithmetic rewards substantial, mobile income — the higher it runs, the harder a fixed fee is to argue with. Where earnings are modest or anchored to one country, the fee can cost more than it saves, and Dan says so early. The island itself — the villa market, the quiet of Meads Bay, arrival via St. Maarten — has its own full jurisdiction guide on the Anguilla page; the two are best read together.

Dan calls Antigua & Barbuda's version the unadvertised option: a permanent-residence route with a flat annual tax of US $20,000 — an established arrangement that almost nobody markets, inside a jurisdiction most families encounter only through its citizenship program. It reaches clients through advisors rather than advertising.

It fits families who already hold Antiguan citizenship, or are acquiring it: the passport does the mobility work, and permanent residence anchors a clean tax story on an island where the family already keeps a home. The day count is modest enough that families who already own on Antigua rarely change how they live; I confirm the current presence and filing requirement in writing before you spend anything on the file.

At the other end of the ladder sits Roatán, the largest of Honduras's Bay Islands, where Dan cites a flat-tax residency in the region of US $5,000 a year. For a first offshore base — a trial of island life before committing serious capital — it is the most accessible arrangement on this page, on an island with an English-speaking heritage and direct flights from North America.

The honest note: Roatán is not a British Overseas Territory, and the difference shows — infrastructure, banking depth and institutional maturity sit well below Anguilla's, and the legal framework is Honduran rather than British. Dan presents it as exactly what it is: the right first rung for some families, the wrong permanent base for most of his private clients.

Barbados earns its place for a different reason: it runs no flat tax. New tax residents can instead be taxed on a remittance basis — foreign income is taxed only when brought into the island, while what stays offshore stays outside the net. The discipline is managing remittances rather than paying one agreed figure, but the effect for a family whose wealth works abroad is similar in spirit: a contained, predictable relationship with the local tax system.

For families who want a full-service island — established professional services and direct long-haul connections — it belongs in the comparison. The mechanics are on the Barbados residency page.

None of this is a Caribbean invention. Switzerland's lump-sum — forfait — taxation lets qualifying foreign residents negotiate a fixed assessment with their canton in place of tax on worldwide income. Italy offers new residents a flat annual tax that stands in for tax on foreign-source income. Greece runs a non-dom regime doing similar work for new tax residents. The model is global — and the Caribbean versions are simply closer to home for North American families: same time zones, short flights, and a property the family will actually use.

A flat-tax residency is rarely the whole plan. Dan's sequencing settles the tax residency first — the family's base is where the arithmetic lives — then layers a second citizenship on for mobility, and lets the real estate carry both, as Anguilla's property requirement is built to do. For US citizens who prefer to stay inside the US system, Puerto Rico's Act 60 is the alternative he prices against all of the above.

The American caveat runs through every arrangement on this page: US citizens are taxed on worldwide income wherever they live, so a flat tax does its full work only alongside the far larger step of renouncing US citizenship — never first, and never lightly. Non-US families can generally put these arrangements to work directly. For how the region's residency programs compare more broadly, start with residency by investment.