9 Best Caribbean Islands to Retire

Puerto Rico

Puerto Rico offers many advantages for retirees seeking a tropical climate while still technically remaining in the United States. Health care is widely available, and Medicare is accepted. Retirees can own property in this U.S. territory without restrictions or visas. For qualified people, the Individual Investors Act waives island and federal income taxes on dividends, interest, and capital gains for residents who live in Puerto Rico for at least 183 days of the year.

The cost of living is around eight percent lower than in the rest of the U.S., while rent is roughly 42 percent less. In the major cities, like San Juan and Ponce, English is widely spoken, but it’s helpful to know at least some Spanish. The weather is warm, although humid at times, and hurricane season comes each year from June through November, peaking in August and September.

Several established retiree communities, as well as assisted living facilities, are available throughout the island. Many people have settled around San Juan and the beach neighborhoods to its east.

Isla Mujeres, Mexico

Located about eight miles off the coast of Cancun is the former fishing village of Isla Mujeres—the atmosphere here 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 retirees to rent at a low price, and most residents get around on motorbikes or golf carts, saving the expense of an automobile.

Retirees who qualify financially can apply for a temporary residency visa or permanent visa (after four years) at their local Mexican consulate. Those with legal residency can enroll in public health insurance for a small premium. That said, many purchase private insurance to cover medical expenses or simply pay out of pocket.

U.S. Virgin Islands

The main islands of St. Thomas, St. Croix, and St. John are attractive places to retire for those seeking mild weather, beautiful beaches, outdoor activities, and plenty of choices when it comes to dining. As a U.S. territory, the U.S. Virgin Islands require no visas or passports for relocation. Medicare is accepted, and medical facilities are available on all the islands. The U.S. dollar is the currency, there’s no sales tax, and English is widely spoken.

Note, however, that the overall cost of living is higher than in the U.S., and rents can be on the higher side. Purchasing real estate on the islands works similarly to the mainland U.S., with attorneys representing both the buyer and seller. After a recent visit to the U.S. Virgin Islands, Travel + Leisure A-List advisor Margie Hand said she was “shocked at all the people I met who had retired there,” adding, “Some were working at stores in town, and one 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 more than 40 other small ones. Average high temperatures tend to stay in the high 70s and 80s year-round, and the climate is relatively dry. English is the official language, and the currency is the U.S. 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 to purchase at a range of prices, plus there are no restrictions on foreigners owning property.

The government grants temporary residency visas to investors who purchase property to use as a home. The investment amount varies, depending on the island, and the funds can be used for new construction or put toward the renovation of an older property. There are no taxes on real estate, income, inheritance, or estates.

Anguilla

On Anguilla, the northernmost of the Leeward Islands, the lifestyle is casual, and fishing, snorkeling, golf, tennis, and sailing are popular activities for visitors and residents. The cost of living here is on the high side, but there are no income taxes, VAT taxes, or taxes on capital gains or inheritance.

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

Retirees are able to purchase property with an Alien Land Holding License and additional fees. Those who own property are able to obtain permanent residency. With limited medical facilities on the island, residents may need to travel to nearby St. Martin or one of the other islands for certain health needs, which is something to consider when retirement planning. Some might also opt for private insurance that includes transportation to the U.S. or a large city nearby.

Dominica

Dominica, nicknamed the “Nature Island,” is among the most affordable Caribbean islands to retire to. There’s an income tax based on residency status and income sources, but the destination offers tax incentives for retirees, including a reduced rate for those over age 65. For retirees who decide to make Dominica their permanent home, the Dominica Citizenship by Investment Programme enables foreigners to establish permanent residency by making an investment of at least $200,000 in a government fund or real estate.

Both public and private health care services are available, and private insurance is recommended. Haines, who often spends time with friends who live on Dominica, said, “The island reminds me of Hawaii—very lush with fruit trees and gorgeous 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 most affordable places to retire in the Caribbean. The cost of living here is about 43 percent less than the cost of living in the U.S., while rents are roughly 60 percent lower. The tropical climate, convenient location (about two hours by air from Miami), outdoor activities, and entertainment at resorts and hotels also make the 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 residency 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 in process. 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 American 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 provide plenty of activities and entertainment. While the overall cost of living on Aruba is eight percent higher than in the U.S., rent is generally 25 percent lower. There’s an income tax, but retirees are eligible for exemptions on foreign pensions and annuities.

Quality health care—both public and private—is available, too. American citizens can extend the standard 30-day visa to 180 days as a tourist. To stay longer, an application must be made to the immigration department for a residence permit. A guaranteed annual income of at least $27,778 may qualify applicants ages 55 and over for the status of “retired with guaranteed income.” There are no restrictions on foreigners buying property on Aruba.

Ambergris Caye and Caye Caulker, Belize

Located on Central America’s northeastern coast, just south of Mexico, Belize consists of a mainland area 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 trip from the mainland. On a trip to Ambergris Caye a few years ago, I met retirees from the U.S. and Europe, happily adapting to the slower pace of life, living without cars (just about everyone drives a golf cart), and spending less than they did at home. Caye Caulker is known to be a little more affordable and laid-back since Ambergris Caye is such a hot tourist destination.

The government of Belize offers several options for how to acquire residency or retirement status, whether via the Visitor’s Permit Extension, Qualified Retired Person Program, or permanent residency. Also making Belize an attractive retirement spot, the official language is English, and the currency is the U.S. dollar, along with the Belizean dollar.