9 Best Caribbean Islands to Retire

Puerto Rico

Puerto Rico offers many advantages for retirees looking for a tropical climate while still technically in the United States. Health care is widely available, and Medicare is accepted. Retirees can own property in this US territory without restrictions or visas. For qualified individuals, the Individual Investors Act exempts island and federal income tax on dividends, interest, and capital gains that reside in Puerto Rico for at least 183 days of the year.

Housing costs are about eight percent lower than the rest of the U.S., while rents are about 42 percent lower. In larger cities, such as San Juan and Ponce, English is widely spoken, but knowing at least some Spanish is helpful. The climate is warm, although sometimes humid, and hurricane season occurs annually from June to November, peaking in August and September.

Several established retirement communities, as well as assisted living facilities, are available throughout the island. Many people live around San Juan and the beaches east of it.

Isla Mujeres, Mexico

About eight miles off the coast of Cancun is the former fishing village of Isla Mujeres—the atmosphere is still relaxed, and the cost of living is quite affordable. The small island offers beaches, clear and warm waters for snorkeling and diving, delicious restaurants and a vibrant nightlife scene. Apartments and condos are available for rent at low cost to retirees, and most residents get around on motorcycles or golf carts, saving on the expense of an automobile.

Retirees who are financially eligible can apply for a temporary resident visa or a permanent visa (after four years) at their local Mexican consulate. Legal residents can enroll in public health insurance for a small premium. That said, many people buy private insurance to cover medical expenses or simply pay out of pocket.

US Virgin Islands

The main islands of St. Thomas, St. Croix, and St. John are attractive retirement destinations for those looking for mild weather, beautiful beaches, outdoor activities, and plenty of dining options. As a US territory, the US Virgin Islands does not require a visa or passport to immigrate. Medicare is accepted, and medical facilities are available on all islands. The US dollar is the currency, there is no sales tax, and English is widely spoken.

Note, however, that the overall cost of living is higher than in the US, and rents can be higher. Buying real estate on the islands works much like in the mainland US, with lawyers representing both the buyer and the seller. After a recent visit to the US Virgin Islands, Travel + Entertainment A-List advisor Margie Hand said she was “surprised by all the people I met who had retired there,” adding, “Some were working at downtown stores, and there was an artist who sold pieces to local stores.”

Turks and Caicos

Turks and Caicos is a British overseas territory consisting of eight main islands and over 40 other smaller islands. Average high temperatures are in the 70s and 80s year-round, and the climate is relatively dry. English is the official language, and the currency is the US dollar. “These islands are some of my favorites in the Caribbean,” Hand told T+L. “However, the cost of living may be high for some retirees.” Condos, townhouses, stand-alone residences, and vacant land are available for purchase at various prices, with no restrictions on foreigners owning the property.

The government grants temporary residence visas to investors who buy property to use as a home. Investment amounts vary by island, and funds can be used for new construction or renovation of an older property. There are no real estate, income, inheritance, or estate taxes.

Anguilla

In Anguilla, north of the Leeward Islands, the lifestyle is relaxed, and fishing, snorkeling, golf, tennis, and sailing are popular activities for visitors and residents. The cost of living here is high, but there is no income tax, VAT tax, or capital gains or inheritance tax.

Steve Haynes, a longtime Anguilla resident and a real estate broker at Trophy Properties, represents Four Seasons Anguilla Residences. “The greatest things about the island are the amazing people, the great weather, and the incredible food,” he said. “I’m seeing retirees who buy residences for year-round (living), as well as other people who spend half the year here. It’s a combination of the two.” Haynes also noted that the new Anguilla-Clayton J. Lloyd Airport (AXA), which opens in December 2025, makes the destination easier to reach, ideal for both visitors and residents.

Retirees can purchase property with an alien land holding license and additional fees. People who own property are able to get permanent residency. With limited medical facilities on the island, residents may need to travel to nearby St. Maarten or another island for specific health needs, something to consider when planning for retirement. Some may also opt for private insurance that covers transportation to the US or a nearby major city.

Dominica

Dubbed the “Nature Island,” Dominica is among the most affordable Caribbean islands to retire to. There is an income tax based on residency status and source of income, but the destination offers tax incentives for retirees, including a lower rate for those over 65. For retirees who decide to make Dominica their permanent home, the Dominica Citizenship by Investment program enables foreigners to establish permanent residency by making a real investment of as little as $0.00.

Both public and private health care services are available, and private insurance is recommended. Haynes, who often spends time with friends who live in Dominica, said, “The island reminds me of Hawaii — very green with fruit trees and beautiful scenery. (It’s a) beautiful place to live.”

Dominican Republic

Located on the island of Hispaniola (along with Haiti), the Dominican Republic is one of the cheapest places to retire in the Caribbean. The cost of living here is about 43 percent lower than the cost of living in the U.S., while rent is about 60 percent lower. The tropical climate, convenient location (about a two-hour flight from Miami), outdoor activities, and entertainment at resorts and hotels also make this destination an attractive option for retirees. Most live in Santo Domingo, Santiago, or Punta Cana.

The Dominican Republic offers a retirement visa for long-term residence with modest financial requirements, and those who decide to spend their golden years here can start with a standard tourist visa while the retirement visa is valid. Social Security and pension benefits are not taxable, but income from financial investments such as stocks and bonds, certificates of deposit, and other sources is. International health insurance is recommended for US citizens, as paying out-of-pocket for health care can be quite expensive.

Aruba

This small island in the southern Caribbean offers a stable political climate, warm weather and a location below the hurricane belt. Resorts, museums, shops, and towns offer plenty of activities and entertainment. While the overall cost of living on Aruba is eight percent higher than in the U.S., rents are typically 25 percent lower. There is an income tax, but retirees are eligible for exemptions on foreign pension and annuity payments.

Quality health care—both public and private—is also available. US citizens can extend the standard 30-day tourist visa up to 180 days. To stay longer, a residence permit must be applied to the Immigration Department. A guaranteed annual income of at least $27,778 may qualify applicants age 55 and older for “retiree with guaranteed income” status. There are no restrictions on foreigners buying property on Aruba.

Ambergris Caye and Caye Caulker, Belize

Located on the northeastern coast of Central America, just south of Mexico, Belize consists of a landmass and about 450 islands. Two of the islands (called cays) are popular retirement destinations: Ambergris Caye and Caye Caulker. Both are a short flight or boat ride from the mainland. On a trip to Ambergris Caye a few years ago, I met retirees from the U.S. and Europe who were happily adapting to a slower pace of life, living without cars (almost everyone drives a golf cart), and spending less than their home. Caye Caulker is known to be a bit more affordable and relaxed as Ambergris Caye is a hot tourist destination.

The government of Belize offers several options for obtaining residency or retirement status, whether through a visitor permit extension, the Qualified Retired Person Program, or permanent residency. Also making Belize an attractive retirement destination, the official language is English, and the currency is the US dollar along with the Belizean dollar.