The 12 Best Islands for Retirement, From the Caribbean to the Mediterranean

Malta

Located south of Sicily, Malta has a sunny island climate with temperatures rarely falling below the 50s. English is the second official language of Malta, and many residents speak it and Italian in addition to Maltese. Living costs are somewhat lower than in the U.S., and there's a large expatriate community including both Americans and Europeans, especially those from the U.K.

Healthcare is provided through a public system for those with Maltese or other EU-nation passports, but high-quality private healthcare is also available, typically at an affordable price. Watersports, golf, and other outdoor activities are widely accessible, and Malta is also home to museums, historic sites, and cultural events.

Puerto Rico

Located two hours by plane from Miami and four hours from New York, Puerto Rico offers many advantages as a retirement destination. Medicare is accepted, and healthcare is widely available, especially in or near major cities. As a U.S. territory, Puerto Rico allows property ownership with no restrictions, and no visa is required. For many retirees, another advantage is the Individual Investors Act, which waives island and federal income tax on dividends, interest, and capital gains for residents who live in Puerto Rico for at least half the year.

The cost of living is lower here than in much of the U.S. mainland, with rent prices being regarded as particularly low. Outdoor activities, nightlife, and shopping are readily accessible, with plenty of resorts, restaurants, and shows around to appeal to both tourists and locals. The weather is warm and sunny, although hurricanes and high humidity are part of living in the tropics.

Isla Mujeres, Mexico

This small island is set in the Caribbean Sea, a ferry ride from Cancun, eight miles away. Once a fishing village, the island is now popular with tourists, especially during the winter when snowbirds arrive from colder climates. The weather is warm year-round, though rainy season and potential tropical storms can put a damper on things in late summer and fall. Spanish is the primary language, but English is widely spoken as well.

The island is known for its laid-back culture, and the cost of living is generally lower than in the U.S. Though the currency is Mexican pesos, U.S. dollars are also accepted in many places thanks to the large tourist population; the exchange rate provides good value. Temporary resident visas ranging from one to four years in duration can be earned through modest financial qualifications or certain other provisions, and after four years, it's possible to obtain a permanent resident visa, again through proof of income or savings. Rentals are available in a variety of price ranges, and home ownership is permitted. Private medical insurance is required, and there are pharmacies, doctors, and a hospital on the island. Nearby Cancun offers more extensive options for medical care.

San Juan Islands, Washington

Instead of a tropical island, some retirees prefer cool air, winter snows, and pine forests — and this archipelago in Puget Sound offers all of that in spades. The islands stay cool even in the summer (when temperatures above 80 are vanishingly rare), and, thanks to the shielding effect of the nearby mountains, they get about half the rain of Seattle. Activity peaks here during the summer, when tourists and part-time residents arrive and conditions for hiking and watersports are at their best, but the islands' natural beauty is year-round.

Life in the San Juans is quiet, and some retirees may want to ferry to the mainland for supplies, entertainment, or medical care. With a median home price over $1 million, this isn't a great destination for budget-conscious seniors, but there are some economic advantages — including, notably, that Washington state does not tax social security, pension, or retirement-account income. For a peaceful lifestyle in a healthy, scenic, uncrowded environment, one of the San Juan Islands could be a great choice.

Barbados

Once a British colony, Barbados has retained Commonwealth status since gaining independence in 1966. English is spoken here, and many places accept U.S. dollars, although the island's currency is the Barbadian dollar. Beautiful beaches, friendly people, a stable government and economy, and excellent healthcare make Barbados a popular retirement spot, though not always an inexpensive one since many imports face steep premiums to reach the island. The weather is pleasantly tropical, and the island's location in the eastern Atlantic is away from most hurricane paths.

Foreigners are permitted to purchase property, and retirees over 60 can apply for Immigrant Status with proof of sufficient income. After five years, retirees can also apply for permanent residence. There are expat groups in the major towns, including a large population of British retirees. Residents must pay income tax if they stay on the island for more than half the year, but there is a large allowance for pensioners over the age of 60.

Mallorca, Spain

Mallorca is the largest of the Balearic Islands, located in the Mediterranean off the coast of Spain. Catalan is the official language here, but Spanish is spoken as well. Beaches, sunny weather, mountain scenery, and delicious food attract tourists as well as retirees. Outdoor activities are abundant year-round, and cultural events, shopping, and museums offer plenty to do.

Healthcare is of an excellent quality, and the cost of living is lower than in most U.S. cities. Long-term visas are available, entitling holders to reside, work, study, or conduct research in Spain. Foreigners are permitted to purchase property, and there are also abundant rentals.

Big Island, Hawaii

The largest of the Hawaiian islands offers an astounding eight different climate zones, from sunny, humid coastline to temperate hillsides and frigid mountaintops. With white-sand beaches, waterfalls, and volcanoes to explore, there's no shortage of activity here for outdoorsy retirees.

Hilo, on the island's rainier windward side, is a great home base for seniors. Since most tourists spend their time on the opposite coast, real estate prices are lower here. The lifestyle is quiet in Hilo, though not sleepy, thanks to a vibrant downtown and the presence of a University of Hawaii campus. That said, if cost is not an issue, the Kailua-Kona region on the dry west coast is another good option. It's popular with tourists, which means there are abundant restaurants, spas, golf, and entertainment, and its beaches are warm and sunny year round.

Across Hawaii, property and sales taxes tend to be low. Social security and most pensions are exempt from state income tax, and residents over the age of 60 receive a homestead exemption, further reducing their property tax bill.

Penang Island, Malaysia

This small island off the west coast of the Malaysian peninsula is home to thousands of expats who enjoy the tropical weather, beaches, shopping, restaurants, and entertainment (and the ultra-low rents for modern, spacious apartments). There's much to explore in Malaysia, including rivers, mountains, and jungles. Kuala Lumpur, a modern, sophisticated city, is just a short flight away for a change of scenery.

The "Malaysia My Second Home Programme" (MM2H), a renewable, multi-year and multiple-entry social visit visa, is popular among retirees seeking residency, though ongoing changes to the program mean you'll want to do your homework before you relocate. Once you secure residency, though, pensions and investment income are not subject to Malaysian tax. Another perk: English is spoken in most places, as Malaysia was formerly a British colony.

U.S. Virgin Islands

Three main islands — St. Thomas, St. Croix, and St. John — make up the U.S. Virgin Islands, an easy move for Americans with no passports, visas, or applications required. Surrounded by the Caribbean, with white-sand beaches, rain forests, and coral reefs, the islands blend modern comforts with Caribbean culture. St. Thomas is the most populated of the islands, with resorts, shops, and nightlife. The other islands also offer entertainment and shopping, but are generally more low-key.

English is widely spoken, the U.S. dollar is the currency, and Medicare is accepted. The ease of relocating and the tropical island climate make USVI a great choice for retirees, but be warned there are some drawbacks, including a high price of living and the annual risk of damaging hurricanes.

Dominican Republic

The Dominican Republic is not technically an island — it's one of two nations (the other Haiti) that occupy the island of Hispaniola. Still, it's worth considering for retirees in search of the island life. The D.R. is one of the least expensive destinations in the Caribbean, and at just two hours by plane from Miami, it's easy to get to. Recent years have seen modern upgrades to the local airports, highways, and roads, which only adds to the country's appeal. The tropical climate, beaches, watersports, and outdoor activities all help make this a pleasant place to live.

A pensioners' visa makes retirees eligible for long-term residency by meeting a fairly modest set of financial requirements. Since Medicare and Medicaid do not cover retirees living out of the U.S., private insurance is advised so you can access care in private hospitals, which are generally of higher quality in the D.R. than public facilities. Most expats live in the main cities of Santo Domingo and Santiago, though there are many in popular tourist towns like Punta Cana as well.

Anguilla

Set in the eastern Caribbean, Anguilla is the northernmost of the Leeward Islands, about 165 miles east of Puerto Rico. Sandy beaches, watersports, golf, natural beauty, and luxurious resorts with bustling nightlife provide plenty for retirees to do. Though the high cost of living makes the island a mismatch for budget-conscious seniors, Anguilla offers attractive tax benefits for those who can afford to live here. Residents face no income taxes, VAT taxes, or levies on capital gains or inheritance.

Anguilla is relatively remote, and residents generally travel by ferry to St. Maarten to stock up on supplies. There is only one hospital on the island, so private insurance that includes transportation to the U.S. or a nearby large city is advisable. Foreigners are permitted to purchase real estate on Anguilla with a special license, and rentals are available. English is spoken along with Creole.

Turks and Caicos

Providenciales is the most populous and best-known island in Turks and Caicos, offering white-sand beaches, sportfishing, and world-class snorkeling and diving in its coral reefs. The weather is relatively dry with year-round temperatures in the 80s. Resorts add to the entertainment options with golf, tennis, and shows.

The cost of living is high, but there are no taxes on income, capital gains, or inheritance. Visitors can obtain temporary residence permits, and a residence-by-investment program means that permanent residency can eventually be earned by purchasing real estate. Housing costs vary by island, and there are no restrictions on property ownership by foreigners. Modern medical facilities are available, but private insurance is advisable, including coverage for transportation.