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6 of the Best Places to Retire in the Caribbean

Crashing turquoise waves, blue skies, white sand – a little slice of Caribbean heaven to retreat to, sounds like a dream. And it is attainable for many, even with modest budgets. There are plenty of places in the region that offer not only beautiful scenery, but also good healthcare and a reasonably sized expat population to keep those social circles strong. We’ve selected 6 castles out of thin air that aren’t really that far-fetched. So, if you want to have the necessary knowledge, features, pros and cons about the carribean to help you identify what your version of a golden year paradise will be, then you are at the right place.

  1. Cayman Islands

If your retirement fund is more like a dragon’s hoard than a few bills under your mattress, the region’s most famous tax haven, the Cayman Islands, could 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 frequently positions it in the list of the most beautiful places to visit. There are public and private healthcare options, plus an air ambulance to Miami if needed. The cost of living is nothing to sneeze at, though: It’s nearly 10 percent more expensive to live there than it is in New York City, with the only difference that it is a cheaper home. But you can expect to pay a lot for clothing, food and transportation.

  1. Puerto Rico

Puerto Rico might be your best bet if you like the thrill of living in a different culture without leaving the US 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, food and night scenes, outdoor activities, and beaches that make the island such an alluring 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 complete a month is still 42 percent less than in New York City. Clothes is the only thing that is a little more expensive. Housing and transportation costs, on the other hand, are half or less than half the price.

  1. Anguilla

If you’re just not ready to quit working altogether, Anguilla might be the place to go: there’s no capital gains tax and no personal or corporate income tax. Due in part to its money-friendly tax laws, you’ll find a global expat community here. And while development is tightly controlled, there are plenty of restaurants and nightlife. In addition, immigration is quite simple: if you are retired and have bought a property on the island, it should be easy to obtain residency.

Keep in mind, however, that your home probably won’t be on a sandy beach: private buyers generally won’t be able to buy on the sandy shores reserved for resorts and hotels, which means your shoreline will be rockier. It is also among the most expensive of the Caribbean islands: Costs are only 10 percent lower than they would be in New York, making retirement more expensive than some places in the US.

  1. Curacao

Curacao’s culture is fascinating, with a mix of Dutch, African, and Jewish heritage shining through in its architecture, food, and music. And while it’s a scuba diver’s paradise, there’s an area on the island to suit just about any personality: artistic folks gravitate to Pieter Maai on the secluded west side, for example, while sun worshipers head to the beaches of the East. The weather is sunny nine months of the year, and temperatures hover around 80 degrees. In addition, it offers public and private medical care: St. Elizabeth Hospital is one of the most advanced in the Caribbean. Returning to the United States is also easy: the capital, Willemstad (where the cost of living is about 30 percent lower than in New York), has nonstop flights to Miami and Atlanta.

There are incentives to retire here, too: With the retiree program, there’s no capital gains tax, and income is taxed at just 10 percent; to qualify, however, you must purchase the property within a year and a half and be in at least 50.

  1. Dominican Republic

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

Golf is plentiful, and health care is cheap and easy (many prescription drugs in the US are over-the-counter here). With the cost of living so low, you won’t be alone: ​​the island attracts expats from all over the world. Las Terrenas is a popular spot on the island for retirees – a large French and Italian community has brought amazing food, though expats from all over Europe flock here. However, the area still retains its colorful and charming island vibe, thanks in part to laws that prevent hotel chains from being built here.

  1. US Virgin Islands

The best part about living in the USVI is that you’re still technically in the US, which means you won’t need passports to go back and visit family still on the mainland. And, if you want to work part-time so you don’t get bored, you won’t need a visa to do so. St. Thomas is where most retirees choose to set up shop, and while the island is popular with tourists, the industry has brought many American comforts. Of course, this comes at a price: a three-bedroom rental in the capital of the Virgin Islands will set you back about $2,250 a month, and one outside the city center around $3,000, while other living costs, like food and clothing tend to run a bit more expensive.

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