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The 12 Best Islands for Retirement

Retirement can feel like a daunting major milestone, but if you do proper research and plan, it can be the time to reap the fruits of your lifetime of labor.

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Senior men walking with senior women on the beachkate_sept2004/Getty Images

Living the dream

It’s important to think about your preferred lifestyle during retirement and whether you plan to stay in your current home or pack up and head somewhere warm, like a secluded beach. Of people aged 50 and over, 24 percent say they’ll likely move to a different community, according to a 2018 AARP survey. You’ll have to consider and determine if the following factors align with your finances, such as standard of living, transportation, health care, and lifestyle. But if you’ve dreamed of retiring on a tropical island and living the island life, then here are 12 of the best islands to consider for retirement. Find out the 10 best small towns in America to retire.

Dock, Sand, Sea and Palm TreesIreneCorti/Getty Images

Cayman Islands

Whether you’re looking to learn how to scuba dive, relax on a secluded beach, or get cultured at a museum, each of the three Cayman Islands has its own charm that offers something for everyone. The island is always buzzing with events and festivals like the Cayman Cookout, a week-long food and wine festival at The Ritz-Carlton, Grand Cayman, which draws world-renowned chefs for a celebration of food and libations as well as Pirates Week Festival and Cayman Cocktail Week that also attract locals and tourists alike. Other popular activities include swimming with stingrays at Stingray City, walking through the breathtaking crystal caves, and visiting the botanic park. Aside from the obvious climate and Seven Mile Beach which has been consistently voted as one of the top beaches in the Caribbean, retirees are finding the Cayman Island’s standard of living and array of outdoor activities appealing for retired life. This is the perfect age to retire—and it’s not 65.

Picturesque Renaissance Islands of ArubaChiyacat/Getty Images


The main feature that makes this Dutch island off the coast of Venezuela so attractive for retirement is that it sits outside the hurricane belt which means residents can expect 82-degree temperatures with cooling trade winds all year round. Aruba most recently made Lonely Planet’s Best in Travel 2020 list because of its crystal clear beaches and desert-like terrain in the north shore which make the island accessible to adrenaline junkies and beach-lovers alike. Several airlines including Delta Airlines, JetBlue, and Southwest also fly direct to Aruba which makes it easy if you’re traveling to the United States to visit family and friends. That’s also probably why it’s the most revisited island in the Caribbean.

Galveston Island Historic Pleasure PierDenisTangneyJr/Getty Images

Galveston Island

Just a 45-minute drive south of Houston is an island called Galveston with 32 miles of beaches and pleasant, warm weather year-round. The small beach town is best known for having one of the largest collections of well-preserved Victorian architecture in the country, residing in charming historic districts with rows of colorful homes that are open to the public for daily tours. During the fall and spring, more than 300 species of birds migrate through the island for its natural resources and salt marshes making it one of the top destinations for bird watching. Its close proximity to Houston, one of the largest cities in the nation, also makes it ideal for residents who enjoy weekend getaways to a big city to take advantage of the luxury shopping, cuisine, and arts and culture that Houston has to offer. The Osher Lifelong Learning Institute is also on the island where retirees can take courses such as Tae Kwon Do and cooking.

Surfboard Sunset Silhouettelightphoto/Getty Images

Tamarindo, Costa Rica

Costa Rica has long been a destination for American and Canadian retirees because of its “Pura Vida” mentality (meaning pure life), the high quality of life and affordability. In 2018, AARP ranked Costa Rica as the number one place to retire in the world. While Tamarindo isn’t an island per se, it is a small beach town that is becoming increasingly popular for ex-pats and it is worth noting that it has been published as residing within one of the world’s five “Blue Zones,” where locals live well past the median age likely due to the healthy diet, active lifestyle, beautiful weather, and stunning natural beauty they’re surrounded by on the island. The Central Valley is also a common retirement community mainly because of the active social lifestyle, considering it’s at the epicenter of the nightlife, shops, museums, farmers markets, and classes. Retirees will also be pleased to learn how warm and welcoming locals are to foreigners, also known as “gringos.”

Camara de Lobos - MadeiraJuergen Sack/Getty Images


A quick 90-minute flight from Lisbon, Madeira offers the best of island and city life. The Portuguese island has a good transportation system in place with an excellent highway and railway system and, not to mention, direct flights to major U.S. cities. The capital of the island, Funchal, is slowly becoming a culinary hotspot with two Michelin star-restaurants and farmers markets offering organic fruits and vegetables. It’s also worth noting that English is widely spoken on the island and Portugal has repeatedly been ranked as one of the top safest countries in the world. The 2019 Global Peace Index ranked Portugal as the third most peaceful country in the world, and second in Europe. Learn why more people are going to Portugal to retire.

chairs under palm trees at a beach in Virgin Islandscdwheatley/Getty Images

U.S. Virgin Islands

The U.S. Virgin Islands is made up of three gorgeous (and underrated) islands: St. Croix, St. Thomas, and St. John. Perhaps one of the biggest and most obvious benefits to retiring in the U.S. Virgin Islands is that you are still within the United States so you don’t need a passport and for retirees looking to fill up their days and make extra cash with a small, part-time job, you don’t need a work visa either. You can expect friendly locals, rich culture, delicious food, and weak Wi-Fi (because who’s working anyway?). St. John is arguably the most beautiful island of the three with stretches of white sand beaches and pristine waters that look completely untouched. One visit to Trunk Bay and you may never want to leave the picturesque island. Find out 13 retirement facts you need to take seriously.

A view of a pier with bungalow at sunset in the Caribbean.OLyaL/Getty Images

Ambergris Caye, Belize

In recent years, Belize has become a hotbed for retirees looking for a little slice of paradise. Ambergris Caye, the largest island in Belize, is a playground for retirees who love spending time in the water because there is no shortage of outdoor activities above and below water from snorkeling and scuba diving to fishing and parasailing. Most credit cards are also widely accepted in Belize and English is the official language of the country (other languages are also spoken). Here are 8 things that cost more when you retire.

Anguilla Sunsetstevegeer/Getty Images


The luxury island of Anguilla is a celebrity hotspot because of its laidback lifestyle and unspoiled natural beauty that hasn’t been destroyed by consumerism (yet). “Anguilla is a zero-tax jurisdiction. There are no income, capital gains, profit or other forms of taxation on corporations, regardless of residence status,” according to Deloitte. Additionally, it’s a 20-minute ferry to St. Maarten where you can fly to and from major destinations, enjoy the nightlife scene, go shopping and indulge in outstanding fine dining restaurants. The island boasts 33 white sand beaches, vibrant beachside bars, stunning villas and condos and award-winning spas like Zemi Beach House that is home to the island’s only hammam. The island also offers a plethora of activities for the adventure seeker, including diving, golfing, boat racing, fishing, horseback riding, and more.

boardwalk on the marshmakasana/Getty Images

Pawleys Island

If you’re looking for a small, affordable, laidback beach to call home than look no further than Pawleys Island. Just south of Myrtle Beach, the Town of Pawleys Island, which was incorporated just 35 years ago, has a modest population of 100 year-round residents, unlike other crowded retirement communities such as Florida. South Carolina does not tax Social Security benefits, property taxes are between 4 to 6 percent and the state provides a generous retirement income-tax reduction. For active retirees, the Grand Strand area features award-winning golf courses and Litchfield Beach, just slightly north of the island, has fishing piers where residents in the community can go fishing in the creeks. These are 15 more of the best islands in the United States.

Saint Kitts Panorama with Nevis Island in the background.BriBar/Getty Images

St. Kitts

Tropical climates, magnificent beaches, and outdoor festivals are all good reasons to retire in St. Kitts. But make no mistake, the island is not cheap, however, it is one of the oldest islands to offer the Citizenship by Investment program which is why high-net-worth individuals obtain dual citizenship here. While it’s sister island Nevis, is smaller and offers a more relaxed vibe, St. Kitts is best for those seeking an active retirement. Learn more about the gorgeous Caribbean island you’ve never heard of.

Motorcycle on street, overlooking Caribbean Sea, on Isla Mujeres, MexicoWildroze/Getty Images

Isla Mujeres, Mexico

The low cost of living, mostly sunny weather and close proximity to the United States make Isla Mujeres in Mexico an ideal option for retirees. The island in the Caribbean Sea (near Cancun) is generally considered a hidden island gem because it offers all the benefits of a resort destination without the tourist crowds. If you’re considering buying a home in Mexico, it helps that the U.S. dollar against the peso is strong because your money will go a long way. English is widely spoken around the country and Mexico has been known to have a thriving expat community. Health care is also something to consider when retiring and, fortunately, in Mexico, it’s a fraction of the cost in the United States. Find out the 10 most and least tax-friendly states for seniors.

Various Finds on DaufuskiePenny Britt/Getty Images

Daufuskie Island

This tiny 10-square-mile island just off the coast of South Carolina is accessible only by boat and has caught the eye of many former executives who are looking to slow down. The population of the car-free Daufuskie Island is just under 400 with bikes and golf carts as the main form of transportation. You can learn the history of the island on horseback through guided trail rides or spend the day on a kayak with a tour guide. If you’re more of a foodie, enjoy dining on the freshest seafood like the island’s specialty, deviled crab, or shuck your own oysters at local restaurants. The island is also home to Haig Point, an oceanfront, luxury gated community with a 3-acre equestrian center and Haig Point Club, a notable residential golf course perfect for enjoying life’s simple pleasures. Money tight? Read on for the 15 cheap towns you’ll actually want to retire in.

Leila Najafi
Leila Najafi is a regular contributor to's Travel and E-commerce sections. Her work has also appeared on Thrillist, NBC News, by USA Today, HuffPost, and Eater among other sites. Leila covers destination guides, cultural pieces, home and wellness topics. She earned her MBA from Loyola Marymount University and B.S. in Anthropology from UCLA.

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