Cuba
| Pros |
|---|
| High level of personal safety and low violent crime rates compared to other Caribbean nations. |
| Recent legalization of small and medium private enterprises for limited market-driven business growth. |
| Access to a highly skilled, educated workforce at significantly lower costs than international averages. |
| Cons |
|---|
| Pervasive state intervention in all economic sectors and restrictive centralized control over foreign currency. |
| Frequent power grid failures and unreliable telecommunications infrastructure with daily business operations and logistics disruptions. |
| Absence of robust legal protections for private property and high risk of arbitrary state expropriation. |
Long story short: Starting a business in Cuba usually means a forced marriage with the State, which grabs its cut before you sell a single thing.
Since 2021 though, small private outfits have been popping up all over Havana, and a good bribe unlocks plenty of locked administrative doors. The banking system is flat out dead: you'll pay everything in cash, dollars or black market rate.
Beyond that: daily blackouts, roads falling apart, but Vedado and Miramar stay quiet. Food's good, beaches are stunning.
Will your income be taxed?
Long story short: NO.
Cuba doesn't tax personal income, and nobody comes sniffing around when you settle in. No withholding, no tax return, no centre-of-vital-interests trap waiting to snap shut.
Earn what you want: the taxman here simply doesn't know your name.
Will your wealth be taxed?
Long story short: NO.
Cuba keeps its hands off what you hold. No capital gains tax, no annual wealth grab, no inheritance regime.
Your portfolio compounds in peace and leaves the way it came in; nobody's standing at the door with their palm out.
Easy to run a company there?
Long story short: YES.
Cuba is maximum operational chill: no corporate income tax on standard profits, no criminal liability for misuse of corporate assets, and non-public registries.
The state doesn't take a cut, doesn't park a prosecutor over your intra-company flows, and doesn't put your name in a search box.
VAT sits at n/a. Run your thing; nobody's looking over your shoulder.
A good fit for a holding?
Long story short: NO.
Cuba has no treaty network at all, which buries the holding question, full stop.
Every dividend in or out eats the statutory withholding at full rate, and no domestic regime can patch a hole that sits on the source side. Don't park a holding here.
| Country | Status | Dividends | Interest | Royalties |
|---|---|---|---|---|
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| ∅ // no treaties match | ||||
Easy to come and go?
Long story short: SOME.
Cuba taxes your worldwide income while you're resident, but at least the exit is free: no exit tax on the way out.
Leaving costs you paperwork, not money; your unrealised gains walk out the door with you, untouched.
Is your money watched?
Long story short: NO.
Nobody's reading over your shoulder in Cuba. It has joined almost none of the big automatic-exchange machines (CRS, FATCA, CARF, MLI, MAAC), and its corporate registries are non-public.
Your account movements stay out of foreign tax offices; your name stays out of search boxes. Here, discretion isn't a perk; it's the factory setting.
Is it blacklisted?
Long story short: YES.
Cuba sits on an international embargo list (UN, US or EU sanctions). This is not blacklist friction, it's the financial death penalty: correspondent banking is gone, payment rails refuse the corridor, and simply transacting with the country can put you on a sanctions desk's radar.
Whatever the tax math says, the jurisdiction is radioactive. Walk away.
Do you feel free there?
Long story short: NO.
Press freedom in Cuba is locked down (RSF rank #165). Independent media and civic space operate under pressure (when they operate at all), and that kind of grip usually spills over into economic life too.
Small mercy: crypto isn't formally banned.
Connected to the world?
Long story short: COMPLETELY CUT OFF.
Cuba is unplugged from the global money grid: 0/11 of the services we track work here. No Stripe, no Amazon, and almost nothing around them either.
Whatever your plan is, the payment layer gets built from scratch, with local banks and local rules. Come for other reasons; connectivity isn't one of them.
Other jurisdictions worth comparing
Picked by similarity of strategic profile to Cuba. No editorial ranking — neighbours in the same scoring space.