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Retiring to a Caribbean island is the dream for many Americans and others who want a major change after working for years in concrete jungles like New York. The thoughts of sandy beaches, laid-back vibes, and gorgeous scenery are too hard to ignore.

But which is the best Caribbean island to retire to? For some, the best are main islands that have been developed to offer indulgence and luxury, no matter the cost of living. While for others, an island’s healthcare, location, and ex-pat community are major factors.

Before retiring abroad, here are a few things you’ll want to know to determine which is the best Caribbean island for you.

Cost of Living & Prices

Wherever you head, the cost of living of your destination will impact your finances. Often the places retirees want to go to offer a lot of bang for their buck. Countries like the Dominican Republic, Puerto Rico, and Belize have lower costs of living than in the United States while providing a more comfortable life.

Other countries offset their higher cost of living with favorable tax laws, such as Turks and Caicos and Anguilla. These islands have no taxes on capital gains, inheritance or income – a great benefit to anyone with a fixed income.


Are you renting or buying property abroad? If you have your heart set on livelier, well-developed cities, renting and buying can be very expensive. Prices tend to be lower away from a country’s main islands.

One of the best Caribbean islands to retire to if you want to buy property is Turks and Caicos. Here foreigners don’t have to deal with any restrictions on property ownership. The cost of real estate varies by island, giving you the chance to find gems in places like South Caicos, where beachfront properties are affordable and luxurious.

Medical Care

A core concern to many people is the access and quality of healthcare they’ll have when moving to the Caribbean. You want to make sure you can live the life you want, while carefully tracking your overall well-being.

Barbados, Turks and Caicos, Bahamas, and the Cayman Islands offer some of the best healthcare in the English-speaking regions. Furthermore, these islands offer state of the art facilities.

In the French Caribbean, Martinique, St. Martin and St. Barts are considered to be the top providers of medical care. That doesn’t mean other places don’t have great healthcare systems. Mexico has a high standard of care but it can be limited in more remote areas.

Legal Residency & Visas

You can’t retire to a Caribbean island unless you are allowed to legally reside there. Some countries allow retirees to live there but may take a chunk of your money or overcomplicate things to secure a visa.

Some places, like the Dominican Republic, require proof of income to reside there. In Turks and Caicos, multiple visas can be obtained for temporary residence or permanent status with very little delay and hoops to jump through.

The best Caribbean island for you to live out your days will make you feel welcome, instead of a foreigner.

Friends & Lifestyle

Retiring is not only about clearing a bucket list, it’s about truly enjoying the next phase of your life and making the most of your new-found time. Researching the lifestyle of other retirees and ex-pats in a potential destination will help a lot.

Then there are the activities you’d like to do. Retirees looking to relax on white-sand beaches need to look no further than the shores of Turks and Caicos for villas right next to world-class waters, along with scuba diving and snorkeling.

If you’d like to take your golfing to the next level, the Dominican Republic and Bahamas are known for their elite golf courses which are so beautiful they warrant extra focus while driving your golf cart.

Local Culture

Do you want a completely different experience during retirement? Caribbean countries like Jamaica, Mexico, and Honduras offer lively and energetic evenings you will never get tired of. For those who want calmer, consider remote international living away from the well-developed main islands or a more laid-back culture like those found in Roatan, Honduras.

Places including the U.S. Virgin Islands and Puerto Rico provide you with a sense of familiarity. Things may be more relaxing and paced a bit slower, but you know what to expect for the most part. These American islands also are English-speaking locations that can make it easier to transition into a new place and culture.


Many retirees will have lots of friends and family visiting, on top of doing their traveling. For these people, it will be important to travel easily and conveniently, so living near a major airport may be of high importance.

You’ll want to keep in mind, too, that areas with low accessibility for travel are usually affected by low accessibility in several ways. Getting your favorite wine or fruit at the local grocery store may no longer occur as frequently and consistently as you are used to.

The best Caribbean country to retire to will provide you with access to the kinds of shopping, travel, and activities you are looking forward to the most.

The Top Caribbean Islands to Retire

Turks and Caicos

The country still has its sleepy Caribbean vibe and some of the most beautiful beaches but also offers elite culture and bustling nightlife. With great real estate opportunities and beautiful landscape, it has friendly tax laws for foreigners and offers a retiree lifestyle that is affordable, luxurious, and as adventurous as you want, making it a top Caribbean island to retire to.

Dominican Republic

Full of European flair, Las Terrenas is a choice spot for many retirees due to its government stability and famously low cost of living. It is a great choice for those who want to live their days comfortably without so many luxuries.


Though many locales are fantastic, no other place attracts ex-pats like Ambergris Caye. It is well-located for frequent travel and offers night, daytime, and water activities – perfect for someone looking to be more active.


Whether you are the adventurous retiree looking for a change of lifestyle and scenery or one that wants to settle in a more economically sound location, there is a Caribbean island that is perfect to retire to.