Second citizenship, Caribbean property, and the structure that holds both.

Every family that reaches this practice already has advisors. A capable accountant, a lawyer of fifteen years’ standing, a private banker, a realtor. Each is competent. None of them is wrong. The plan they collectively produce still has a hole in it, because every one of them is optimizing the only piece they can see.

I work the layer above that, so the citizenship file, the property, the entity and the account are not four decisions taken by four people who have never spoken. My team and I are real-estate professionals, investment-migration agents and lawyers, working from five offices — Four Seasons Nevis, Marriott St. Kitts, Jolly Harbour in Antigua, Castries in St. Lucia and Portsmouth in Dominica — so a site visit here is a drive, not a flight.

The costs are concrete. A citizenship application funded from an account nobody cleared in advance, and the file stalls. An approved property bought in a personal name because the ownership question came up after contracts were signed, so the succession plan and the program’s holding requirement now disagree.

None of that is a scandal. It is ordinary, expensive, and a question of order — cheap to get right at the time, costly to unwind afterwards.

As I put it in my piece on why mobility is a portfolio: citizenship governs where you can go, residency governs where you are taxed, and capital governs where your assets sit. Structure sits between the last two, deciding who owns what and what a creditor can reach.

Citizenship is the slowest to obtain and hardest to reverse, so it sets the outer boundary of where a family may live. Residency decides the tax result. Structure is built around the tax position, not the reverse. Capital comes last. Buy the property first, ask about the program second, and the development may never have been approved for it. No family has to use all six — it has to know which piece is load-bearing before anything is signed.

Investment migration comes first. Five Eastern Caribbean nations grant citizenship for a qualifying investment; the comparison page and costs and timelines carry the numbers. On the residency half the day count eliminates more shortlists than price does: Anguilla’s High Value Resident program asks 45 days a year on-island, the Cayman Islands residency certificate 30, Puerto Rico’s Act 60 183.

Real estate here is a paperwork business before it is a property business: a non-citizen generally needs the government’s permission to hold land — 5–10% of the price, three to six months — usually waived on citizenship-approved real estate. Two identical villas at US$800,000 on different islands can land a buyer six figures apart at closing. I walk the projects I represent, say when a deal is wrong, and represent the buyer.

Tax carries the largest financial consequence of the six, and almost every lever has a date attached. I flew out of Canada in 2020 and was taxed in 2021 as though I had sold nearly everything I owned; by then most of the moves that would have shrunk the number had expired — what that actually cost.

Trusts and foundations answer what a creditor can take; companies decide which entity holds the villa, settled before contracts are signed. Banking is considered last and fails first, because a company no bank will take on cannot hold or move anything. Above the account, wealth management and fund management route to regulated partners, and family office services sits above all five.

US citizens remain taxed by the United States on worldwide income regardless of a second citizenship — none of the five Caribbean programs has a US income tax treaty. A jurisdiction levying no local income tax is telling the truth about itself and saying nothing about a US person’s global position: a second citizenship is insurance, not a tax play. These arrangements usually add reporting and deliver no relief. If the objective is to pay less US tax, this is the wrong page.

It begins with one conversation, diagnostic rather than promotional. I read every inquiry myself. I want to know what the family is solving for — mobility, tax base, protection, succession or a transaction — and what already exists: which advisors, which countries, which deadlines. What comes out is a sequence rather than a proposal, and occasionally the honest answer is that nothing should happen for eighteen months.

What this practice owns is the plan every one of those specialists is working to. Where a family needs the work executed rather than coordinated, the introduction goes to a dedicated specialist private-capital practice, and I stay in the chair beside the client. There is no product to place and no fund to fill.