The Best Caribbean Island to Retire: Top Spots for Relaxation

Why Retire in the Caribbean? 3 Key Benefits

The Caribbean offers a unique blend of advantages that make it an attractive retirement destination. Here are three key reasons why you might consider making the move:

●       Availability of Citizenship by Investment: five of the Caribbean Citizenship by Investment Programmes allow retirees to live freely in the country indefinitely and wide visa-free or visa-on-arrival travel to multiple countries.

●       Climate and Natural Beauty: tropical weather, sweeping beaches and stunning flora and fauna make the Caribbean an ideal retirement location.

●       Relaxed Lifestyle: the Caribbean is rightly famous for its laid-back approach, just right for your golden years.

How to Choose the Best Caribbean Island: Main Factors

​​Each island has its unique characteristics, so it's essential to find one that aligns with your lifestyle, preferences, and needs. Here’s what you should think about.

Taxation

You have earned your retirement, and taxation can have a significant effect on your income going forward. The good news is that all five Caribbean Citizenship by Investment Countries:

●       impose no tax on capital gains and inheritance;

●       only charge personal income tax on income earned in the relevant country. Antigua and Barbuda and St Kitts and Nevis have zero personal income tax.

So far, so good. However, if you retain citizenship in your home country, you will also need to consider the tax implications of dual citizenship to ensure that there is no double taxation. Vago has written an excellent blog on dual citizenship.

Taxation in each country depends on your tax residency status. The general rule is that if you spend more than 183 days in the relevant country, you will become a tax resident of that country, but some jurisdictions have additional rules. Therefore, you will need to consider the tax implications in your home country, particularly if you intend to split your time between the two countries.

Each of the Caribbean Citizenship by Investment Countries imposes taxes on property, including:

●       taxes on property, including stamp duty and/or transfer tax on purchase and/or sale; and

●       annual property taxes (ranging from 0.1% in Antigua and Barbuda to around 1.25% in Dominica for residents).

Finally, each of the Caribbean Citizenship by Investment Countries imposes withholding taxes on non-tax residents for interest, dividends, and royalties derived from the relevant country.

Safety and Security

The safety and security of your chosen retirement spot will make a difference. This can be broken down into two main areas: crime; and natural disasters.

Crime

All countries suffer crime, however, the five Caribbean Citizenship by Investment Countries are all considered to below-risk in terms of crime, generally with rates of crime commensurate or lower than much of Europe and the US. Most crime is non-violent, with low-level the usually topping the list of types of crime committed. Police and criminal justice systems are well-developed and the countries have a significant interest in keeping crime under control as they rely on tourism as a major source of income.

Natural Disasters

Natural disasters can occur anywhere, but the most relevant risk in the Caribbean Citizenship by Investment Countries is the risk of hurricanes. The intensity and risk of hurricanes varies, with a trend for the more northern islands to be at higher risk than those more to the south. The islands are well-prepared for minor hurricanes (if that is not a contradiction in terms!) as they will typically be affected by some each year.

The official season for hurricanes is June through November, with August through October being the highest risk. The Caribbean Citizenship by Investment Countries are on the edge of the hurricane belt, and the strength of hurricanes is generally not life-threatening, provided suitable steps are taken to prepare and take shelter. Given the hurricane risk, insurance for real property is essential and relatively costly.

Cost of Living

Healthcare

All five Caribbean Citizenship by Investment Countries other than St Kitts and Nevis have public healthcare systems which are generally available for no charge to all citizens. St Kitts and Nevis operates a different model under which there is no national health service but medical services (other than eye and dental care and prescription drugs) are heavily subsidised by the government and reduced to zero in the case of citizens under 18 or over 62. The healthcare systems in each of the Caribbean Citizenship by Investment Countries are improving as the countries further develop and are projected to continue improving over the short to medium term with significant investment in training and facilities being made.

Prescription drugs that you may use regularly may not be available on the islands and so those with specific need sin this area should check with the local health authorities and take suitable supplies with them if necessary.

Each country also has private healthcare facilities, which are, as you might expect, of a higher quality and accessibility than state institutions. As such, it is recommended that private healthcare insurance is obtained to ensure access to the best care and to cover transfer to other jurisdictions in the event that the local healthcare system is not sufficient.

Accessibility

Accessibility focuses on two areas: the ability to travel to and from the country of choice and the ease of moving around within the country.

Travel

Each of the Caribbean Citizenship by Investment Countries has an international airport. In addition to flights to local destinations, direct flights to major hubs are available, and a list of such hubs for each country is set out below.

Accessibility in the Countries Themselves

All the Caribbean Citizenship by Investment Countries are relatively small islands. Public transport is inexpensive but also not generally frequent, it doesn’t always cover where you wish to go and taxis are expensive. If you intend to live in an area well-served with amenities, this will be less of a concern. Anywhere else a car is almost a must if you want to get around easily, and this comes at a cost. Import taxes make cars considerably more expensive than you might expect and fuel is also relatively costly.

Road conditions vary among the Caribbean Citizenship by Investment Countries, with St Lucia (especially in the north of the island) and Grenada being the best developed, and Dominica being the least well served. Connectivity by road to the airport and other amenities will be an important factor to consider in choosing both the island itself and the location within the chosen island.

Accessibility for people in wheelchairs or with other mobility issues is not as advanced as in the US or Europe. On the flip side, it is likely that as the countries develop further, accessibility will become more of a priority and should improve. 

5 Best Caribbean Islands to Retire: Your Tropical Oasis

Let’s look country by country at some of the other main areas for consideration when selecting which of the five is the best Caribbean island to retire for you.

Antigua and Barbuda

Climate

Culture

Nature

Governance

Events

Antigua and Barbuda enjoys a tropical maritime climate, characterised by warm temperatures year-round, with an average of 27°C (81°F). The islands have a relatively dry season from January to April, with a wetter season from May to November. The islands have robust infrastructure and emergency systems in place to manage such events.

Originally inhabited by the Arawak and Carib peoples, the islands were colonised by the British in the 17th century. The cultural landscape is a blend of African, British, and indigenous influences. This rich history is reflected in local music, dance, and festivals, with calypso, reggae, and steelpan music being particularly popular. Cricket, a legacy of British rule, is the most popular sport, and sailing is also popular, reflecting the islands' strong maritime culture.

Antigua and Barbuda boasts 365 beaches, one for each day of the year, along with coral reefs, lagoons, and lush vegetation. The country’s landscape is primarily flat, with rolling hills and volcanic rock formations. The islands are also home to rich biodiversity, making them a haven for nature lovers.

Antigua and Barbuda have a stable democratic government based on the British parliamentary system. The country is generally regarded as having a manageable level of bureaucracy, with a reasonably straightforward process for interacting with government agencies. Retirees will find that essential services like renewing a driver’s licence, paying taxes, or obtaining necessary permits are relatively simple, although some processes can be slow due to limited resources. The government has been making strides in digitising services to reduce in-person visits and streamline processes.

Antigua and Barbuda is known for its lively events and festivals, particularly Carnival, one of the year's most anticipated events. Antigua Sailing Week is another major event, attracting sailors and spectators from around the world. These festivals are deeply rooted in the local culture and provide a vibrant social scene for retirees.

Dominica

Climate

Culture

Nature

Governance

Events

Dominica has a tropical rainforest climate, with high humidity and heavy rainfall, particularly on the windward side of the island. Temperatures are warm year-round, averaging 26°C (79°F), with cooler conditions in themountainous interior. The island’s lush greenery is a result of its abundantrainfall.

Dominica's culture is a vibrant mix of indigenous Kalinago heritage, African traditions, and European colonial influences, particularly French and British. The island was originally settled by the Kalinago people, and their influence is still present today, especially in the Kalinago Territory. African traditions have also left a profound mark, particularly in the island’s music, dance, and festivals. Dominica’s outdoor sports are heavily influenced by its rugged terrain, with hiking and diving being popular among locals and expatriates alike, although there is of course cricket for those with more sedentary dispositions.

Known as the "NatureIsland," Dominica is characterised by its rugged terrain, rainforests ,waterfalls, and geothermal activity. The island is home to the UNESCO-listed Morne Trois Pitons National Park, as well as numerous rivers and lakes. Dominica’s unspoiled natural beauty is a major draw for retirees who appreciate ecotourism and outdoor adventures.

Dominica’s government operates under a parliamentary democracy, with a legal system rooted in English common law. While the country’s bureaucracy is smaller and more accessible, some processes can be slow, particularly in rural areas. However, the government is generally cooperative and accommodating, particularly for expatriates. It’s advisable to have local assistance or a legal advisor to navigate more complex processes, such as property transactions or dealing with land registries.

Dominica hosts several unique cultural events, including the World Creole Music Festival and Carnival. The island’s festivals are deeply connected to its Creole heritage, offering retirees a chance to immerse themselves in local traditions and music. Dominica’s Independence celebrations also feature traditional dances, music, and cuisine.

Grenada

Climate

Culture

Nature

Governance

Events

Grenada has a tropical climate with relatively consistent temperatures throughout the year, averaging around 28°C (82°F). The dry season runs from January to May, while the wet season is from June to December. Although Grenada is located on the southern edge of the hurricane belt and is less impacted the another Caribbean islands, it is not immune to these storms as has been seen recently with Hurricane Beryl. The island has since improved its hurricane preparedness and infrastructure resilience and the value of these improvements has led to greater preparedness for such events.

The island was originally inhabited by the Arawak and Carib peoples before being colonised by Europeans. Grenadian culture is characterised by a strong sense of community, vibrant music, and dance traditions, such as calypso and soca. French influence on the island is evident in its place names and culinary traditions. Cricket and football are the most popular sports, and sailing and water sports are also widely enjoyed.

Known as the "SpiceIsle," Grenada is famous for its aromatic plantations, waterfalls, and pristine beaches. The island’s volcanic origin provides a diverse landscape of mountains, rainforests, and coastal areas. Grenada’s natural beauty is complemented by its extensive marine life, making it ideal for snorkelling and diving.

Grenada also follows a British-style parliamentary democracy. The country’s bureaucracy is relatively user-friendly, with many government processes being straightforward and accessible. Retirees generally find it easy to interact with government departments for routine tasks such as registering a vehicle, renewing licences, or paying taxes.

Grenada’s Spicemas Carnival is the island’s most significant cultural event, celebrated with colourful parades, music, and dance. The island also hosts the Grenada Sailing Festival and the Pure Grenada Music Festival, both of which attract international visitors. These events provide a lively social calendar for retirees.

Saint Kitts and Nevis

Climate

Culture

Nature

Governance

Events

Saint Kitts and Nevis has a tropical climate, with temperatures ranging between 24°C (75°F) and 31°C (88°F) throughout the year. The islands have a dry season from December to April and a wet season from May to November. Located within the hurricane belt, Saint Kitts and Nevis is vulnerable to hurricanes, especially between June and November, but the islands have strong building codes and disaster response plans in place to reduce the impact of the senatural events.

The cultural heritage of Saint Kitts and Nevis is shaped by its history of indigenous Carib and Arawak inhabitants and European colonisation. Saint Kitts was the first Caribbean island to be colonised by the British, and Nevis has a rich history as a major sugar producer. The islands' cultural roots are a blend of African, British, and French influences, reflected in the local cuisine, music, and festivals. Cricket and football are deeply ingrained in the local culture and, along with sailing and hiking, are integral to the islands' cultural life.

The twin islands of Saint Kitts and Nevis are known for their volcanic mountains, rainforests, and beaches. The islands are home to the UNESCO World Heritage site of Brimstone Hill Fortress and offer stunning views from places like Mount Liamuiga. The islands’ natural beauty is one of their strongest appeals to retirees.

Saint Kitts and Nevis operates under a stable parliamentary democracy, with governance structures similar to those of other Commonwealth countries. The islands have a relatively low level of bureaucracy, and dealing with the government on a day-to-day basis is generally straightforward. Most routine administrative tasks, such as obtaining permits, paying taxes, or registering property, are manageable, although some processes can take longer than expected due to limited staffing. The government is trying to modernise its operations, including digitising more services, which should help reduce delays and improve overall efficiency.

The islands of Saint Kitts and Nevis host several vibrant festivals, including Carnival, the Saint Kitts Music Festival, and Culturama, which is unique to Nevis. These events celebrate local culture, music, and heritage, offering retirees plenty of opportunities to engage with the community and enjoy local traditions.

Saint Lucia

Climate

Culture

Nature

Governance

Events

Saint Lucia enjoys a tropical climate with warm temperatures year-round, typically ranging from 25°C (77°F) to 30°C (86°F). The dry season extends from December to May, while the wet season is from June to November. Saint Lucia is situated near the edge of the hurricane belt, making it prone to hurricanes and tropical storms but less so than those further north. The government has invested in improving hurricane preparedness and infrastructure resilience to protect the island from future storms better.

Saint Lucia's culture is a unique blend of African, French, and British influences, reflecting its complex history of colonisation. The island was originally inhabited by the Arawak and later the Carib people, before being contested by the French and British for centuries. The French influence is particularly strong in the island's Creole language, cuisine, and Catholic traditions, while British colonial rule has left its mark on the legal system and sports, particularly cricket. The island’s dramatic landscapes, including the iconic Pitons, provide a stunning backdrop for outdoor sports like hiking and diving, which are popular among locals and retirees alike.

Saint Lucia is famous for its dramatic Pitons, volcanic peaks that rise sharply from the sea. The island’s landscape includes rainforests, beaches, andSulphur Springs, the Caribbean’s only drive-in volcano. Saint Lucia’s natural beauty is among the most striking in the Caribbean, attracting retirees who enjoy outdoor activities and scenic views.

Saint Lucia’s government is a parliamentary democracy, and the country has a reputation for a relatively efficient bureaucracy compared to other Caribbean nations. For retirees, dealing with the government is typically hassle-free for most day-to-day tasks like renewing a driver’s licence, paying taxes, or obtaining residency permits. Saint Lucia has been proactive in improving its e-government services, allowing for easier access to information and quicker processing of certain requests online.

Saint Lucia is famous for its Jazz and Arts Festival, which attracts international artists and music lovers. The island’s Carnival is another major event, featuring parades, music, and dancing. Additionally, the La Rose and La Marguerite festivals celebrate the island’s unique cultural heritage, offering retirees a rich cultural experience.

Enhancing Your Caribbean Retirement: Bonus Insights

Finally, some other factors to consider when determining which island is best for you. Each of these factors will vary in importance depending on their importance to you.

Language

Size of Country and Population

All of the Caribbean Citizenship by Investment Countries are small islands (or groups of islands) with commensurately small populations. This maybe exactly what you want in your retirement but bear in mind small size means a limited range of goods and services and a lack of economy of scale generally.

Quality of Infrastructure

Technology and Connectivity

Food (Local and Imported)

All five islands take food seriously as apart of the culture and as part of community and family life. Each island is similar in this respect, with fresh seafood, tropical fruits, and vegetables being widely available and inexpensive. Anything that requires importing from abroad will be expensive due to customs duties. Many rural islanders grow their own food, with Dominica being a particular example due to its rich soil. Supermarkets are present in each country, but many prefer to visit local markets and buy directly from the producer.

Final Thoughts

Choosing the best Caribbean island to retire to is a big decision with many factors to take into account, from financial considerations such as taxation and cost of living, through safety and security and healthcare, to issues more of personal taste such as culture and the local environment.

Which is best suited for you will depend on balancing many of the above factors, and there is no substitute for spending time ‘in-country’ to get a feel for whether it is the place for you.