Best places to live in the Caribbean
The cities we compare in the Caribbean, ranked for a couple who want a safe, stable, mild and fairly priced place to live. The order comes from our match model, the one that ranks a couple's results after the quiz, run with the answers a typical couple might give. 11 of the 188 best-known cities we rank qualify; these are the top 11.
12 questions, about 4 minutes, no account needed. Taking the quiz is free, and so is seeing your #1 city. Full results for both of you are a one-time US$12 (€12 in Europe).
The ranking
1. Bridgetown, Barbados
70% match- Safety index
- 68/100
- Healthcare index
- 70/100
- Est. cost
- €3,205/mo
- Avg temp
- 27°C
2. Saint John’s, Antigua & Barbuda
69% match- Safety index
- 65/100
- Healthcare index
- 65/100
- Est. cost
- €3,007/mo
- Avg temp
- 27°C
3. San Juan, Puerto Rico
68% match- Safety index
- 55/100
- Healthcare index
- 68/100
- Est. cost
- €3,210/mo
- Avg temp
- 27°C
4. Castries, St. Lucia
68% match- Safety index
- 62/100
- Healthcare index
- 62/100
- Est. cost
- €2,742/mo
- Avg temp
- 26°C
5. Basseterre, St. Kitts & Nevis
68% match- Safety index
- 68/100
- Healthcare index
- 64/100
- Est. cost
- €2,819/mo
- Avg temp
- 27°C
12 questions, about 4 minutes, no account needed. Taking the quiz is free, and so is seeing your #1 city. Full results for both of you are a one-time US$12 (€12 in Europe).
6. The Valley, Anguilla
67% match- Safety index
- 78/100
- Healthcare index
- 66/100
- Est. cost
- €3,360/mo
- Avg temp
- 27°C
7. Providenciales, Turks & Caicos Islands
66% match- Safety index
- 78/100
- Healthcare index
- 68/100
- Est. cost
- €3,444/mo
- Avg temp
- 27°C
8. Kingstown, St. Vincent & Grenadines
65% match- Safety index
- 62/100
- Healthcare index
- 60/100
- Est. cost
- €2,644/mo
- Avg temp
- 27°C
9. Nassau, Bahamas
64% match- Safety index
- 55/100
- Healthcare index
- 68/100
- Est. cost
- €3,713/mo
- Avg temp
- 26°C
10. Saint George's, Grenada
64% match- Safety index
- 65/100
- Healthcare index
- 62/100
- Est. cost
- €2,560/mo
- Avg temp
- 27°C
11. George Town, Cayman Islands
64% match- Safety index
- 80/100
- Healthcare index
- 78/100
- Est. cost
- €3,892/mo
- Avg temp
- 28°C
Source: the datasets behind our city pages. Cost is our model estimate (a country-level cost index scaled for city size); temperature from the Open-Meteo archive (2019 to 2023 averages); rainfall from TerraClimate (1991 to 2020 normals); safety and healthcare are our own country-level estimates; internet from the Ookla Speedtest Global Index; English from the EF English Proficiency Index; residency from our hand-reviewed residency dataset (not legal advice).
How this list is ranked
This ranking is our match model, the same one that ranks a couple's shortlist after the quiz, run with the preset answers in the table as if one person had given them. Each answer sets a target on that factor, every city is scored on how close it comes, and the importance levels weight those scores: each step from Minor to Essential counts three times the one before. The match is the weighted average, from 0 to 100%.
| Factor | Answer | Importance |
|---|---|---|
| Cost of living | Balance cost & quality | Major |
| Climate | Mild all year | Major |
| Urban density | Mid-size & walkable | Minor |
| Religion & tolerance | Open & secular | Some |
| Political climate | Strong, stable democracy | Some |
| Safety | Very safe | Some |
| Healthcare | Top-tier care | Some |
| Infrastructure & internet | Fast & reliable, always | Minor |
Skipped, so they do not move the order: taxes, geography & region, language & culture, proximity to home.
Safety, healthcare, political climate (the EIU Democracy Index), religion and tolerance, English and internet speed are country-level figures, so every city in a country shares them. Climate, distance to the coast, terrain relief and city size are measured per city, and cost is a country-level index scaled for city size. In the driest places (under about 250 mm of rain a year), terrain relief and a mild, four-season or cold climate count for less, down to half where it never rains.
With no passport to go on, the model treats residency as neutral, and the lists leave out countries our residency rating calls hard to obtain for most foreigners (under 40 out of 100). In the quiz, each partner's passport and your household budget decide this instead, moving cities you could not get residency in to a separate list.
The lists also leave out cities in a country or region under a US State Department "Level 4: Do Not Travel" advisory, since our safety figures are country averages. The quiz leaves them out too.
Only cities with a location in the Caribbean are ranked.
We rank each country's three best-known cities with full country data, the ones most read about on English Wikipedia over the past year, so lesser-known towns do not lead on figures their country shares. A city under 100,000 people counts only if it is its country's best known, since island and city states belong on this list; any other is passed over for the next best known.
Suburbs are folded into their main city, as in the quiz and on our comparison pages: a city within 25 km of a larger one in the same country (30 km in the same state or province) is left out, and so is any city within 15 km of a national or state capital, so Zapopan counts as Guadalajara and Quezon City as Manila. A national capital or seat of government is never folded. At most three cities per country make the list, so one country cannot fill it.
Costs are our model estimate, in euros, of what a couple spends a month living centrally. They start from our own country-level cost-of-living index (New York = 100) and rise with city size. They come from our city dataset (last rebuilt June 2026), not a survey of current prices, so use them to compare cities rather than to set a budget.
Temperatures are 2019 to 2023 annual averages from the Open-Meteo archive; rainfall is the TerraClimate 1991 to 2020 annual normal.
Every figure here is the same one shown on the city's own page.
Your answers will differ from these. Take the quiz with your own answers and the same model ranks the cities for the two of you.
Can you get residency there?
This list does not know your passports. Whether a couple can actually live in one of these places depends on both partners' nationalities and on your household income and savings, which set the residency routes open to you. Each city's page lists the routes we track for its country, and our visa income table sets each country's income bar next to a couple's monthly costs.
The OurNextCity quiz asks for each partner's passport and your household income and savings, and moves cities where residency looks out of reach for the two of you into a separate list.