With a growing economy, seven international airports (more than any other Caribbean country) and five modern highways that crisscross the country in less than three hours, the Dominican Republic is more convenient than most islands.
The Dominican Republic is a favorite of nature lovers who come to see the humpback whales in the waters around Samana.
On a monthly budget of $2,000, a couple can live the good life with nights out on the town, plenty of play on a myriad of golf courses and household help.
For those who prefer to own rather than rent, you can snag a one-bedroom condo for $100,000 in the cosmopolitan capital city of Santo Domingo and in towns on the north coast. Real estate in the touristy areas like Punta Cana and Puerto Plata come with a higher price tag.
Away from the congested resort towns, Samaná is off the beaten track with three main towns, uncrowded palm-fringed beaches and waterfalls.
The biggest town, called Las Terrenas, is charming with béisbol games in the park, fried fish on the beach and, courtesy of the international community of expats, grocery stores that stock flaky French croissants, piquant German salamis and pastas from Italy.
Rincón Beach in Samaná on the northeast tip of the country is popular with retirees.
Not as pricey as some other Caribbean islands, many find Antigua’s British vibe their retirement cup of tea. There are more than 300 sublime beaches, restaurant stock is growing, nightlife is worth staying up for and the sailing scene attracts fans from around the world.
Although there are no targeted incentives for retirees apart from no wealth, inheritance or personal income tax, those who want long-term residency status submit a bank letter or pension statement for approval. For retirees in a rush, the process is often completed within three months.
Antigua's Sheer Rocks restaurant dishes up fine fare with exceptional views.
A pioneer in Caribbean medical tourism, the Cayman Islands also offer what the locals call a friendly tax system (you might call it offshore banking), high standard of living, top-notch restaurants, plenty of shopping, superb diving and a tight-knit expat community mostly in Grand Cayman’s capital city of George Town.
Seven Mile Beach is the iconic beach in Grand Cayman.
Sun, surf and Seven Mile Beach aside, another big ticket for retirees is healthcare. Health City Cayman Islands offers retirees cutting-edge medical care.
A favorite of those who squirreled away a generous retirement portfolio, the busier west side is full of real estate options and for those who prefer to strap on scuba gear or hop on a kiteboard, the east side is the place to hang your hat.
With year-round sunny weather and a reliable infrastructure, Curacao is a top pick with retirees who covet a city vibe, vibrant art scene in the picturesque capital city of Willemstad, stunning beaches dotting the coastline, diverse community of expats and an increasing number of nonstop flights from the U.S.
From exploring the storied streets and picturesque bridges in the capital city of Willemstad to mountain biking, golfing and diving, the island is a big hit with retirees.
Hot spots for house-hunters include the trendy east side near the Jan Thiel Beach.
Curacao's capital city Willemstad is chockablock with charming spots to take five.
For those looking for more than a palm-dotted tax haven, Angilla impresses with 33 postcard beaches, more than 100 restaurants, swanky resorts, opulent villas, funky dive bars on the beach and a melting pot of expats from all over the world.
In Anguilla, Cerulean Villa is on the market for 20 million dollars.
The five-bedroom Arushi Villa is on Rendevous Bay beach.
Ultimacy Villa is on the market for $5,500,000.
Four Seasons Anguilla Resort is where upscale villas are also for sale.
In Anguilla, active retirees go for the green at the Cuisinart Golf Club.
Jackie Cestero is one of those expats who, along with her husband, sold their home in upstate New York, packed a 20-foot container, boarded a plane with their collie Sheyne and never looked back.
Mead's Bay is one of 33 beaches that rim the coastline.
The Bahamas is not only a magnet for sun-seeking tourists but also for retirees.
Harbour Island is where golf carts are the transport of choice, pink sand beaches stretch along the eastern shore and the architecture is pleasantly reminiscent of New England.
The Bahamas' close proximity to Florida means grandparents are not too far from the grandkids in the U.S., there is no foreign language to learn and the pace of life is charmingly slow.
If you speak Spanish or want to learn, you’ll be right at home in Puerto Rico. Like the U.S. Virgin Islands, Puerto Ricans are American citizens (although without a vote in presidential elections).
Shopping is a popular Puerto Rican pastime, with designer boutiques on beachfront promenades, and U.S. chains like Walmart, Walgreens and Starbucks everywhere.
Retirees can enjoy dance classes in open-air markets.
Kayaking through the bioluminescent bays is popular with nature lovers.
The currency is the U.S. dollar, Medicare is valid and electric plugs are the same as they are at home.
The trio that makes up the U.S. Virgin Islands — St. Thomas, St. John and St. Croix — offers some of the best retirement scenarios in the Caribbean.
On St. John, Trunk Bay Beach is the recipient of umpteen "best beach in the Caribbean" awards courtesy of the pearly sand and clear water.
St. Thomas is the top choice for tax-free shopping, nightlife in the cruise port of Charlotte Amalie and lazy days in Magens Bay with a 1-mile stretch of perfect beach and acres of coconut groves.
If a small-town vibe is what you’re looking for, Nevis may be your island.
Across the channel from St. Kitts, the pretty isle is full of lures like no tax on inheritances, foreign income or capital gains, and a second passport with a real estate buy of at least $150,000 (U.S.).
Nevis is home to the Robert Trent Jones II golf course at the Four Seasons Resort Nevis.
Casa Azul at the Four Seasons Nevis Resort is close to the golf course.
Pinney's Beach is on the west coast of Nevis.
Cheryl Andrews is a U.S. citizen who owns a house on the island that she rents when she is not living in it.