Your first 90 days in the Caribbean: 2026 deadlines

The table below covers the 12 destinations where we track arrival rules. 'Registration deadline' is when you must act relative to your entry stamp; 'tax identifier' is the number that unlocks banking and employment. Each government sets its own rules — the entries reflect the published requirements.

One detail worth flagging before you read on: Curaçao drives on the right, unlike every other destination in this comparison. If you're island-hopping, that's the one that will catch you.

Every country here ties its registration clock to the date the officer writes in your passport — not to your intended stay, not to your visa category, not to what the airline told you. Read that stamp before you leave the arrivals hall.

Three destinations stand out for short or unpredictable windows. In Dominica, the initial stamp can be as short as 21 days — set by the officer, not by your ticket. In St Lucia, 6 weeks is common; people plan for 3 months and get a nasty surprise at departure when they've overstayed. Curaçao adds a second layer: you must register with the Kranshi (Civil Registry) within days of arrival, separately from the residence permit application. Missing the Kranshi step blocks everything downstream.

The Bahamas is the outlier in the other direction — visitors can be admitted for up to 8 months at the officer's discretion, but the Department of Immigration wants the residence permit file in well before that expires, and processing takes months. Starting late is the most common mistake.

For remote workers, three countries offer purpose-built long-stay visas that sidestep the standard permit queue: Barbados's Welcome Stamp (12 months), Bermuda's Work from Bermuda certificate (12 months), and Dominica's WIN visa (18 months). All three are applied for before travel. The WIN and Work from Bermuda certificates are the only routes where the clock doesn't start running after you land.

Most Caribbean destinations have no personal income tax, so new arrivals assume the local tax ID is irrelevant. It isn't. The identifier — whether it's called a TIN, TRN, NIB number, BIR number, or persoonsnummer — is the number banks, landlords, utilities, and employers key off. Without it, account opening stalls.

Jamaica makes this explicit: the TRN is the island's universal identifier, and banks treat it as a hard prerequisite. Get it in the first week. It's free and fast, but nothing else moves until you have it. Trinidad and Tobago's BIR number works the same way — banks routinely ask for it during onboarding, and employment can't proceed without it.

In Curaçao, the persoonsnummer (also called the crib number) is issued through the Kranshi registration. That's why the civil registry deadline matters so much: the tax number, the bank account, and the residence permit all trace back to that first step.

The no-income-tax headline is real across most of these destinations, but it doesn't mean no tax questions at all. Antigua, St Kitts and Nevis, Anguilla, the Bahamas, and Bermuda all levy no personal income tax. Grenada taxes locally sourced income but not foreign income of non-domiciled residents. Barbados exempts Welcome Stamp holders earning only foreign income. What none of these rules change is your home country's position — the US taxes citizens on worldwide income regardless of where they live, and other countries apply their own tie-breaker tests.

Caribbean banking onboarding is consistently demanding across the region — reference letters, source-of-funds documentation, proof of address, and a valid permit are the baseline almost everywhere. The reasons vary: some islands are rebuilding compliance reputations, some host large citizenship-by-investment programmes that attract scrutiny, and all of them operate under international AML pressure.

Two destinations have friction beyond the standard document list. In Trinidad and Tobago, the real problem isn't onboarding — it's what happens after. Access to US dollars is rationed in practice, international card spending faces limits, and a local account won't reliably fund overseas obligations. Arrange the cross-border side before you need it. In the Bahamas, a homeowner's card or residence permit makes the difference between a routine account opening and a refusal — the compliance rebuild is visible in the process.

Several islands share the Eastern Caribbean dollar, pegged at 2.70 to the US dollar — Antigua and Barbuda, Dominica, Grenada, St Kitts and Nevis, and St Lucia all use it. That removes exchange risk within the currency union but doesn't make international wires fast or cheap. Bermuda and the Bahamas use currencies pegged 1:1 with the US dollar, and US notes circulate freely in Bermuda. Curaçao uses the Netherlands Antillean guilder, also pegged to the US dollar, but has exchange-control licensing on some cross-border flows.

The practical answer for most arrivals is a multi-currency account held abroad, used in parallel with the local account. Banking that works before the local account exists covers the options we track. US persons face FATCA screening at every bank in this region — that's not a reason to avoid local banking, but it does mean the process takes longer.

Across most of the Caribbean, the arrival pattern is the same: present a valid foreign licence, pay a fee, and receive a temporary local permit over the counter. That gets you legal immediately. Longer-term residents then convert to a full local licence — sometimes on paper, sometimes with a written and practical test.

Jamaica and Trinidad and Tobago both accept a valid foreign licence or International Driving Permit for a period after arrival — Jamaica specifies up to 12 months — before requiring conversion through the local licensing authority, which involves a written and practical test for most applicants.

Bermuda is the exception that stops people cold: non-residents and most permit holders cannot own or drive a car at all. The island limits households to one vehicle tied to the property. Newcomers get around on scooters, buses, ferries, and taxis. A foreign licence lets you rent a scooter, not a car. If your life plan involves a car, Bermuda isn't the destination.

Almost every destination drives on the left. Curaçao drives on the right. The Bahamas drives on the left but most cars are US left-hand-drive imports — that combination is the local hazard that catches arrivals off guard.

Each destination has a specific trap that the published rules make clear but that arrivals routinely miss. These aren't edge cases — they're the things that change the financial or legal picture for a significant share of newcomers.

• Anguilla: Medical evacuation is the real financial exposure. A single air ambulance off-island runs into tens of thousands of dollars, and standard travel policies cap far below that. Verify the evacuation limit and the receiving hospital network in writing before you rely on a policy. See Anguilla: the full arrival playbook for the full detail.
• Antigua and Barbuda: No income tax does not mean no tax residency questions back home. The US taxes citizens on worldwide income regardless, and several other countries apply tie-breaker tests. Get the home-country position advised before restructuring anything around the zero-tax headline. Full detail: Antigua and Barbuda: the full arrival playbook.
• Bahamas: Annual residence permits are exactly that — annual, discretionary, and renewed at the department's pleasure rather than by right. If you intend to stay long-term, start the permanent-residence route early. Full detail: Bahamas: the full arrival playbook.
• Barbados: The Welcome Stamp does not create residence and does not count toward immigrant status. People plan around it as a first step toward staying; the published rules make clear it is not. Full detail: Barbados: the full arrival playbook.
• Bermuda: Cost of living and the one-car-per-household rule are the two things people most underestimate. The car rule applies to the house, not the person. Budget and transport plans built on mainland assumptions don't survive the first month. Full detail: Bermuda: the full arrival playbook.
• Curaçao: The Dutch connection misleads people constantly. Curaçao is not in the EU, not in Schengen, and a Dutch or EU residence permit buys you nothing at the immigration counter. Plan the file as you would for any non-EU country. Full detail: Curacao: the full arrival playbook.
• Dominica: Hurricane exposure is the planning fact nobody puts in a checklist. Maria in 2017 destroyed a large share of the island's housing stock. Check the building standard of anything you rent or buy, and confirm your insurance covers named-storm damage before the season starts. Full detail: Dominica: the full arrival playbook.
• Grenada: Beryl in 2024 devastated Carriacou and Petite Martinique — the risk is current, not historical. Confirm named-storm cover, the deductible, and whether your policy pays for temporary accommodation before you sign a lease or purchase. Full detail: Grenada: the full arrival playbook.
• Jamaica: Get the TRN in the first week. It's free, fast, and almost nothing else works without it — banking, utilities, employment, even a mobile contract. Personal-security planning by neighbourhood also matters more than the tourist experience suggests. Full detail: Jamaica: the full arrival playbook.
• St Kitts and Nevis: A CBI passport is a travel document, not a tax plan. Your home country's rules on citizenship or residence-based taxation don't change because you acquired a second nationality. Get that advised before the investment, not after. Full detail: St Kitts and Nevis: the full arrival playbook.
• St Lucia: Watch the length of the entry stamp rather than the visa-free headline. Six weeks is common; overstaying is treated seriously at departure. Diary the actual date written in your passport on the day you land. Full detail: St Lucia: the full arrival playbook.
• Trinidad and Tobago: The foreign-exchange squeeze changes daily life — expect limits on USD purchases and on international card spending. Do not plan to fund overseas obligations out of a local account. Arrange the cross-border side before you need it. Full detail: Trinidad and Tobago: the full arrival playbook.

The sequence is roughly the same everywhere: read your entry stamp, register with immigration or the civil registry, get your tax identifier, then open a local bank account. The tax number unlocks the bank account; the bank account unlocks rent and utilities. Trying to do these out of order adds weeks.

While the local account is being set up — which can take weeks in document-heavy markets — a multi-currency card or foreign account covers daily spending. Banking that works before the local account exists covers the options we track for the interim period.

Healthcare enrollment is the step most people defer and then regret. Healthcare enrollment, by country has the country-level detail on what's available to permit holders versus citizens, and what the gaps look like. The Anguilla evacuation trap is the most dramatic version of this problem, but coverage gaps exist across the region.

Each government makes the actual determination on your permit and registration — the published rules are the framework, but officers have discretion on timelines and documentation. Apply early, bring more documents than the list requires, and don't assume the island pace means deadlines are flexible. For the full arrival playbook for any destination, see every first-90-days playbook.