These Caribbean Islands Are the Best Places to Retire, According to Travel + Leisure

Tropical Caribbean beach with green trees and white sand inviting retirement living

These Caribbean Islands Are the Best Places to Retire, According to Travel + Leisure

Tropical Caribbean beach with green trees and white sand inviting retirement living

Staff

Tropical climates, slower living, and lower costs are pushing more Americans to look beyond the mainland for retirement. According to a recent report by Travel + Leisure, several Caribbean destinations stand out for retirees seeking sunshine and financial advantages.

The islands offer a mix of affordability, tax incentives, and established expat communities. With New Jersey leading the nation in outgoing residents, these destinations offer plenty of perks for retirees looking to exit the state.

U.S. Territories Offer Easy Transitions

For Americans, Puerto Rico and the U.S. Virgin Islands remain among the easiest places to retire to. Because both are U.S. territories, retirees don’t need visas, and Medicare is accepted, making the transition to island life much easier.

Puerto Rico stands out for its lower living costs. On average, Puerto Rico is about 8% cheaper overall than the mainland, with rents significantly lower. Tax breaks are also available for residents who qualify. 

The Virgin Islands offer familiar incentives. English is the primary language, and the U.S. dollar is the currency.  However, unlike Puerto Rico, living costs can exceed those of the mainland.

Tax Incentives and Residency Perks Attract Buyers

It’s not just U.S. territories that are drawing retirees. Other Caribbean islands remain popular for expats due to financial benefits tied to owning property. 

In Turks and Caicos, there are no taxes on income, inheritance, or capital gains, and buying property can help qualify for residency.

Aruba offers certain exemptions on retirement income, while Dominica provides tax reductions and a citizenship-by-investment program.

Meanwhile, Anguilla combines tax advantages with luxury real estate options. However, healthcare access remains limited. 

Lower Costs Drive Interest In Other Destinations

Affordability is a major factor in several top retirement picks.

The Dominican Republic has living costs roughly 43% lower than the U.S., according to the report, and rents can be up to 60% cheaper.

Belize, particularly the islands of Ambergris Caye and Caye Caulker, appeals to American retirees with English as the official language and residency programs designed for newcomers. 

And just off Mexico’s coast, Isla Mujeres offers low living expenses and accessible health care options through residency programs.

Retirement Migration Is Accelerating

The ranking reflects a broader trend. Retirees can look outside of the mainland for their new home. Some of the most gorgeous tropical climates in the Americas offer lower costs, tax advantages, and more to attract retirees. 

Combine that with warm temperatures, ocean views, and a slower pace of life and it remains obvious why retirees continue to look to these Caribbean islands for relocation. 

The New Jersey Digest is a new jersey magazine that has chronicled daily life in the Garden State for over 10 years.