Best Caribbean Island to Retire – Everything You Need to Know!

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The Caribbean is a popular retirement destination, with its white sand beaches, warm tropical climate, natural beauty, more relaxed lifestyle, and welcoming Caribbean culture. With over 700 islands, islets, reefs, and cays, it can be overwhelming to decide where to spend your golden years and enjoy a relaxing retirement.

In this guide, we’ll explore the region and help you choose the best Caribbean island to retire for you, assessing safety, quality of life, and cost of living. So, let’s dive straight in!

The Best Retirement Destination in the Caribbean 2024

The Caribbean is a subregion of the Americas, with some of its islands bordering the Caribbean Sea and the Atlantic Ocean. The region is generally known for its fantastic weather of tropical climates, relatively low cost of living, great tax incentives for individuals and businesses, good healthcare options, beautiful beaches, and friendly locals.

The eastern Caribbean includes destinations like the US Virgin Islands, the British Virgin Islands, St Maarten, Puerto Rico, and the Leeward and Windward Islands. The western Caribbean is home to places like Aruba, the Bahamas, Cuba (the largest island), the Florida Keys, and Trinidad and Tobago.

There are many expats scattered across the different Caribbean islands based on their needs. The more expensive islands offer luxury living and exclusivity, while more affordable Caribbean countries (such as Dominica) can offer a more tranquil lifestyle away from bustling tourist crowds. That’s why the best island for expat retirees will depend on their individual needs.

In the next section, we’ve put together a list of some of the best islands to retire in the Caribbean – in no particular order.


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Anguilla is a small Caribbean island known for its beautiful beaches, coral reefs, stunning resorts, and peaceful lifestyle. While the island is small, it is perfect for retirees looking for less hustle and bustle. There are also a variety of activities on offer to help you maintain an active and healthy life, such as cycling, horseback riding, golf, tennis, and water sports like snorkeling, sailing, and diving.

Antigua and Barbuda


Antigua and Barbuda is one of the most prosperous nations in the Caribbean, making it one of the best islands for expats considering retiring to the Caribbean. English is the official language spoken here, but you’ll also hear Spanish and Portuguese on the island.

The nation offers many modern healthcare facilities, a tropical climate, picturesque landscapes, and stunning beaches with turquoise blue waters perfect for swimming, snorkeling, kayaking, and more. The country also has good connections to the US, Canada, and Europe, making international travel relatively easy. It is also one of only five Caribbean countries that offer a citizenship by investment (CBI) program, allowing foreign investors to obtain Caribbean citizenship by making a qualifying investment in the country.

Check out our guide to the Antigua and Barbuda Citizenship by Investment Program to find out more.

Take a look at our Antigua and Barbuda Citizenship Ultimate Guide by local experts



Have you ever asked yourself, Where is the best Caribbean island to retire cheap? Well, many people would say Dominica. The ‘Nature Island’ of the Caribbean offers sandy beaches, tropical weather, a variety of entertainment options, and a low cost of living.

Yes, the cost of living in Dominica is relatively low when compared to the US, the UK, and other islands in the Caribbean. For example, in the capital city of Rosseau, the cost of renting can start from as low as $200 per month for a one-bedroom apartment outside the city center.

Dominica also offers excellent tax benefits. For example, residents do not pay wealth tax, gift tax, inheritance tax, or capital gains tax. In terms of medical care, Dominica offers public and private health care.

Dominica’s citizenship by investment program is one of the most affordable CBI programs in the Caribbean, with the minimum investment starting from $100,000. To learn more, check out our Ultimate Guide to Dominica Citizenship by Investment.

Take a look at our Dominica Citizenship Ultimate Guide by local experts

Dominican Republic


The Dominican Republic is known for its beaches, resorts, and golf, and often ranks high on the list of best places to retire in the Caribbean. The nation offers plenty of cultural and recreational activities with its museums, festivals, water sports, and local cuisine and food availability.

To retire in the Dominican Republic, you can apply for a Pensionado Visa, a residence permit issued to a pensioner or retired foreigner looking to reside in the country during their retirement years. The visa requirements include the following:

  • Minimum monthly pension or retirement of $1,500 ($1,750 for couples)
  • Passport
  • Residence Visa
  • Birth certificate
  • Four photos
  • Police clearance certificate
  • Certified proof of pension origin
  • Bank certificate from a Dominican bank
  • Apostilled or legalized marriage certificate, declaration of singleness, or proof of living together
  • A guaranteed travel insurance policy contracted with insurers authorized by the Director General de Migración (DGM)
  • Medical examinations



Grenada is known as the Caribbean’s ‘Spice Isle,’ as a major export of the island is spice. Grenada offers some world-class beaches, fantastic weather, a host of cultural events, and a relaxed lifestyle. If you are interested in retiring to a calm and peaceful neighborhood and still enjoying a good quality of life, then Grenada is for you.

Additionally, Grenada offers a citizenship by investment program that allows foreign retirees to obtain citizenship by making a qualifying investment in the country’s economy. To learn more, visit our guide to Grenada Citizenship by Investment.

Take a look at our Grenada Citizenship Ultimate Guide by local experts


Montserrat is widely considered one of the safest places to retire in the Caribbean. This British territory is located in the Leeward Islands and offers access to coral reefs, black sand beaches, and captivating seaside caves. The island is considered to have a relatively low level of crime and violence, making it one of the safest places to retire in the Caribbean.

Healthcare facilities are more limited here, with only one hospital on the island and several clinics and health centers. The island is quiet and laidback, offering plenty of opportunities to birdwatch, hike, snorkel, and enjoy a game of dominoes with locals and other expats. The island is prone to natural disasters, so it’s important to research the best places to settle on the island.

St Kitts and Nevis

St Kitts-and-Nevis

St Kitts and Nevis is a twin-island nation located between the Caribbean Sea and the Atlantic Ocean. Known for its lush rainforests, breathtaking scenery, epic hiking trails, and white sand beaches, this Eastern Caribbean island also offers the oldest citizenship by investment program in the world.

St Kitts is the more developed of the two, with tourists flocking to its shores to enjoy the golden sunshine and international living experience mixed with the picturesque surroundings of island life. Nevis is more rustic than St Kitts and offers a slower, more tranquil way of life.

Take a look at our St Kitts and Nevis Citizenship Ultimate Guide by local experts

St Lucia


St Lucia is famous for its epic diving sites, natural beauty, palm trees, fantastic white sand beaches, and stunning mountain ranges. St Lucia’s stable government is an attraction of the island, as is the low cost of living, affordable health insurance, and beneficial tax incentives.

English is the official language here and the cost of living in St Lucia is more affordable than in the US and the UK, making it one of the best Caribbean islands to retire to from the UK and the US in many expats’ eyes. Additionally, the Caribbean paradise is full of entertainment opportunities, such as surfing, snorkeling, and hiking, has a selection of fine dining options and beach bars, and offers the option to obtain citizenship through the St Lucia Citizenship by Investment Program for a minimum economic investment of $100,000.

Check out our guide to St Lucia Citizenship by Investment for more information.

Take a look at our St Lucia Citizenship Ultimate Guide by local experts

St Maarten


Next is St Maarten, which is part of the Kingdom of the Netherlands. The country boasts a diverse community, an evolving economy, delicious fresh produce, and a stunning natural landscape. This Caribbean country also offers a relatively affordable cost of living, good value medical care options, and is one of the safest places to retire in the Caribbean.

St Maarten also offers a pensioner’s permit (penshonado). The pensioner’s permit is a great attraction of St Maarten as it enables you to live there as a permanent resident. The following documents are required:

  • Copy of your valid passport
  • Original birth certificate
  • Original police record
  • Original marriage certificate (if applicable)
  • School registration for any children (if applicable)
  • A letter of consent of custody for any children if one of the parents of one or more of the children will remain in the country of origin (if applicable)
  • Proof of income

You can visit the government website to find out more about the pensioner permit requirements.

US Virgin Islands


Considered one of the best places to retire to from the USA, the US Virgin Islands offer beautiful beaches, crystal-clear waters, and a taste of island life. In 2020, the US Census Bureau found that 16 percent of the population was older than 65, making this a top territory with a large retirement population.

What is even more attractive is that the territory has no specific retirement age mandated by law, meaning you are free to retire here whenever you desire, provided you can support yourself financially. While the cost of living here is generally higher than in the other Caribbean islands mentioned in this article, the territory does offer good tax benefits to retirees, a tropical climate with plenty of activities to keep you entertained, and a diverse and welcoming cultural landscape.

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Frequently Asked Questions about the Best Caribbean Island to Retire to

There are many excellent retirement destinations in the Caribbean. The best island for you will depend on your requirements. For example, Dominica is widely considered one of the most affordable Caribbean islands for retirees, while Montserrat often ranks among the safest islands. 

Other Caribbean countries popular among foreign retirees include Grenada, St Kitts and Nevis, and St Lucia, as they offer citizenship by investment programs. The investment routes include real estate options, which can be attractive for future retired expats looking to relocate to the island.

Depending on the Caribbean island, you’ll find quality private clinics or hospitals and even medical facilities specializing in specific ailments. If you are an American citizen, you may find that your health insurance extends to places like Puerto Rico and the US Virgin Islands. Alternatively, private health insurance (expat insurance from an international company or health insurance from a local provider) is available in the Caribbean, often at a lower cost than in countries like the US and the UK.

The Caribbean islands are relatively safe for those looking to enjoy a relaxing retirement. In fact, many islands boast a low crime rate. Some of the safest islands to retire to in the Caribbean include:

  • Antigua and Barbuda
  • Anguilla
  • British Virgin Islands
  • Cayman Islands
  • Martinique
  • Montserrat
  • St Barts

Most Caribbean countries are relatively safe to live in, but Antigua and Barbuda is one of the most popular retirement destinations among American, Canadian, and British retirees due to its reputation for safety, which can be attributed to its low crime rate and political stability.

Many retirees (and future retirees) look to make a Caribbean paradise their future home and enjoy a peaceful, relaxing lifestyle. The best Caribbean islands for this include:

  • Puerto Rico
  • Turks and Caicos
  • Barbuda
  • Bahamas
  • Cayman Islands
  • Nevis
  • British Virgin Islands

You can bring your pet with you when you retire in the Caribbean. You must obtain a valid veterinary import permit prior to your move in accordance with the destination island’s requirements. The requirements differ across the islands, so it is essential to check the specific requirements you need to meet before relocating. You must also pay an import fee and may need to pay an inspection fee upon arrival.

As the Caribbean consists of many diverse cultures and languages, you may experience some barriers when relocating. This does provide a greater opportunity to find an island with a culture and language you are familiar with. For example, Spanish-language expats from Costa Rica (Central America) will find a large Spanish-speaking community. There are also many English-speaking islands, such as Grand Cayman (Cayman Islands), St Kitts, and St Lucia.

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