6 of the Best Places to Retire in the Caribbean

Crashing turquoise waves, clear blue skies, white sand -- a little slice of Caribbean heaven to retire in sounds like a dream. And it’s an attainable one for many, even on modest budgets. There are plenty of places in the region that offer not only gorgeous scenery, but also good healthcare and a reasonably sized expat population to keep those social circles strong. We’ve spun six castles out of the air that aren’t actually all that farfetched -- keep reading to see which one is your version of a golden-years paradise. 

1. Cayman Islands

If your retirement fund looks more like a dragon's hoard than a few bills under the mattress, the region's most notorious tax haven, the Cayman Islands, might be your dream destination. The British Overseas Territory probably has one of the highest standards of living in the Caribbean, and its Seven Mile Beach regularly makes the most-beautiful lists. There's public and private healthcare options, plus an air ambulance to Miami if needed. However, the cost of living is nothing to sneeze at: It's almost 10 percent more expensive to live there than in New York City, with the only difference being cheaper housing. But you can expect to pay a lot for clothing, food, and transportation.  

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2. Puerto Rico

Puerto Rico might be your best choice if you'd like the thrill of living in a different culture without leaving the U.S. -- and want to brush up on your Spanish along the way (hey, you're never too old to learn something new!). You'll still pay in dollars, you can access Medicare, and Walgreens is just around the corner. But you'll also have the history, culture, culinary and nightlife scenes, outdoor activities, and beaches that make the island such an attractive destination in the first place. The cost of living isn't bad, either: In the capital of San Juan, the amount of money it takes to make it through a month is still 42 percent less than in New York City, with clothing being the only thing that's a bit more expensive. Housing and transportation costs, on the other hand, are half or less than half the price. 

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3. Anguilla

If you just aren't ready to completely stop working, Anguilla might be the place to go: There's no tax on capital gains, and no income tax for individuals or companies. Due partly to its money-friendly tax laws, you'll find a global community of expats here. And while development is tightly controlled, there are plenty of restaurants and nightlife. Plus, immigration is fairly straightforward: if you're retired and have purchased property on the island, it should be simple to get residency. 

However, be warned that your home probably won't be on a sandy beach: On the whole, private buyers are restricted from buying on the sandy coastlines reserved for resorts and hotels someday -- which means your coastline will be a rockier one. It's also among the pricier of the Caribbean islands: Costs are just 10 percent less than they would be in NYC, making retirement there more expensive than in some places in the U.S. 

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4. Curaçao

Curaçao's culture is fascinating, with a blend of Dutch, African, and Jewish heritage shining through in its architecture, food, and music. And although it's a diver's paradise, there's an area on the island to fit pretty much any personality -- for instance, artsy folks gravitate toward Pietermaai on the secluded west side, while sun worshippers head to the beaches out east. The climate is sunny nine months of the year, and temperatures hover right around 80 degrees. Plus, it offers public and private healthcare -- St. Elizabeth Hospital is one of the most advanced in the Caribbean. It's also easy to get back to the States: The capital, Willemstad (where the cost of living is about 30 percent less than in NYC), has nonstop flights to Miami and Atlanta

There are incentives to retire here, too: With the pensioners' program, there's no capital gains tax, and income is taxed at just 10 percent -- to qualify, though, you have to purchase property within a year and a half and be at least 50.

One downside is that taxis are really expensive, but depending on where you live, you might not be taking one all that often.

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5. Dominican Republic

If the financial crisis took a chunk out of your retirement savings, you don't have to write off your dreams of spending your twilight years on the beach. The Dominican Republic is incredibly affordable for many Americans, and it's especially charming outside of the tourist-filled resort towns like Punta Cana. As long as you have $1,500 a month coming in somehow (like through Social Security pensions), you can get a residency permit here -- and it'll go far, with that same amount more than easily getting you through the month. Plus, you can bring over your household goods and car tax-free, and it's easy to work if you want to take a part-time job. 

Golf is plentiful and healthcare is cheap and easy (many prescription meds in the States are over-the-counter here). With the cost of living this low, you won't be alone: The island draws expats in from all over the world. Las Terrenas is a popular spot on the island for retirees -- a large French and Italian community has brought some amazing food, though expats from all over Europe flock here. However, the area has still retained its colorful, charming island vibe, thanks in part to laws that prevent chain hotels from building here.

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6. U.S Virgin Islands

The best part about living in the U.S. Virgin Islands is that you're still technically in the U.S., meaning that you won't need passports to pop back and visit family still on the mainland. And, if you want to take on a part-time job to keep from getting bored, you won't need a visa to do it. St. Thomas is where most retirees choose to set up shop, and although the island is popular with tourists, the industry has brought in many American conveniences. Of course, this comes at a price: A three-bedroom rental in the U.S.V.I.'s capital, Charlotte Amalie, will run you about $2,250 per month, and one outside of the city center about $3,000, while other living costs, such as food and clothing, tend to run a bit pricier. 

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