The Best Islands for Retirement

Category: International Retirement

November 4, 2014 — Have you ever dreamed about retiring on an island? A relaxing place with warm breezes, the gentle sound of lapping waves, endless sunshine, and friendly locals? You certainly wouldn’t be the only person to share that dream. This article will review the pros and cons of island living, plus share 2 list of islands that might be good retirement spots – a domestic list we created and another, the 10 best tropical island retirements from

There are islands – and there are islands
Some people’s idea of an island for retirement might be domestic, such as an island on a big lake in Michigan, one of the many off of the Maine coast, Catalina Island near Los Angeles, or the San Juan Islands northwest of Seattle. There there are places on the East Coast, many of them barrier islands.

But for other folks the only islands they are interested in are tropical ones, which almost always means foreign locations. Most are relatively close to the US, usually in the Caribbean. Although there are some great islands in few are in Europe, Africa, or Australia/New Zealand, NextAvenue did not choose any of those.

Time of year
Some islands are better for year round living than others. Those in the Caribbean or Southeast Asia never get cold. However they can be susceptible to hurricanes or typhoons in season. Islands in America’s Northeast or Midwest not only get pretty darn frosty, they can also be impossible to get on or off in the depths of winter. For that reason many islands are really only appropriate as part time retirement residences.

The decision to live on an island is a very personal choice. You have to know what you like, and what parts of ordinary life you can stand to miss. Here are some of the advantages of an island retirement:

Peaceful. Life slows down when you are on “Island Time”.
Beautiful. Surrounded by water, the bays and coasts and the vegetation are picturesque.
On the water. Big bodies of water moderate the air temperature, keeping you cooler in summer and warmer in winter.
Recreation. There is swimming, boating, fishing. Usually there is a lot more, since most islands are resorts with things for tourists to do when not sitting on the beach.
Casual lifestyle. Your editor, who lives most of the year in Key West, has never worn a tie there. Long sleeve dress shirts and slacks hang unused in the closet. People are less formal in every way, with flip flops and shorts the order of the day.

Not all of the disadvantages of island living are immediately apparent. It might take weeks, months, or even years to discover some of the hidden issues that affect those who try island living. Here are some:

Claustrophobic. Many aspects of island can get to you. Your circle of friends will be limited. It is hard to get on and off the island. Tourists might start to get on your nerves.
Transportation. You will probably pay more to come and go, and have fewer options. On the other hand, you might not need a car.
Limited culture. Some big islands have cultural opportunities, either on or just off. But many times you will be limited to a small library and whoever is performing at the hotel.
Medical. This can be the scariest limitation, particularly as our list of baby boomer ailments grow. You don’t want to be in a small clinic with a big problem. And being medevaced is expensive and scary.
Expense. Just about everything on an island except coconuts and fish has to be imported, and you will pay a price for that. Shopping and variety are limited.
Evacuations. Another thing that no one enjoys is a mandatory evacuation order. Getting off the island in the face of a natural emergency can be frightening and is always inconvenient.

8 Best USA Islands for Retirement
We think these make great places to retire, but are not listed in any particular order.


San Juan Islands, Washington. There are 450 islands northwest of Seattle, although only 4 have ferry service. Orcas Island is the largest.
Port Isabel, Texas. In southernmost Texas, Padre Island is a barrier island resort with great beaches.
St. Simons Island, Georgia. This is one of the Golden Islands at Georgia’s southern tip. There is great golf in this upscale community. Sea Island is just above it.
Amelia Island, Florida. This barrier island is a resort and large development in northern Florida’s east coast. The charming village of Fernandina Beach is just above it.
Marco Island, Florida. This relatively new area is at the bottom of Florida’s Gulf Coast. There is a lot of tourism and developments. For people who might get bored there, bustling Naples is just up the road.
Hawaii. Like they say, the island of Hawaii, the Big Island, is big. It is home to several towns including Hilo on the east coast and – Kailua-Kona on the west. Then there are the other Hawaiian Islands including Oahu, Maui, and Kauai. They are so beautiful you will easily get used to seeing lots of vowels in your place names and local words.
Sunset Beach, North Carolina. Located on a barrier island in southern North Carolina, this small community has wonderful beaches.
Martha’s Vineyard, Massachusetts. Favored by many Presidents for family vacations, Martha’s Vineyard offer a laid back and self-contained universe. There are beautiful beaches, farms, and charming little towns. In winter life slows way down, although it isn’t as cold as on the mainland. The island of Nantucket is nearby, but it is even smaller and more expensive.

10 Best Tropical Islands for Retirement developed this list of the 10 Best Tropical Islands for Retirees. Use this link to find out more about these islands. We think it is a pretty interesting list – in fact we had never heard of most of them before! The author of the article, Park Wilson, is an American expat living in Panama. He has a website,, which is definitely worth a look.

Note that some of these islands are referred to as archipelagos, which means a group of islands or a stretch of water containing many islands.

1. Caye Caulker, Belize. A 5 mile long and casual island in the Caribbean off the coast of Belize.

Willemstad, capital of Curacao. (Photo by Wikipedia and Mtmelendez)

Willemstad, capital of Curacao. (Photo by Wikipedia and Mtmelendez)

2. Curacao, Dutch Caribbean. Willemstad is the capital, which offers a blend of Dutch culture with Latin spice. Curacao is near the coast of Venezuela.

3. Boca Chica, Panama. NextAvenue describes this Pacific Coast archipelago as an undiscovered and “up and coming” place for expat retirees in the very retirement friendly country of Panama.

4. Roatan, Honduras. One of the Bay Islands, it is on the mesoamerican reef, 2nd largest in the world.

5. Nevis, Lesser Antilles. Next to St. Kitts, and 200 miles from Puerto Rico.

6. Isla Mujeres, Mexico. It’s across the bay from Cancun.

7. San Andres, Colombia. An archipelago off Columbia’s Caribbean coast. The ecosphere is quite interesting.

8. Pearl Islands, Panama. It is about 30 miles from Panama city . Panama has a stable government and uses the US $ as its official currency.

9. Palau, Micronesia. A nation of 250 islands with friendly immigration policies. It is near Indonesia and the Phillipines.

10. Dominica, Lesser Antilles – Nature Island of the Caribbean

For further reading
Affordable Places to Retire on the Waterfront (2 parts)
Best Places to Retire on a Lake (2 parts)

What do you think about an island retirement, tropical or not? Have you had experiences living on an island? Please use the Comments section below to share with your fellow members.

Posted by Admin on November 4th, 2014


  1. Hilton Head Island is large enough to not even feel like an island. Biking trails make it easy to get anywhere on the island. Great golfing and tennis are readily available. Restaurants offer diverse menus and cultural heritage venues can be found. Wide beaches with dolphins swimming by are not to be missed.

    by Rich — November 5, 2014

  2. A Rich difference here. Hawaii is a gorgeous, wonderful place, but quite remote — though many islanders routinely fly to the west coast.

    We also spent some time on St. John / St. Thomas and would like to visit St. Croix. I could easily slip into St. John island time. Hopefully, because of it’s park status, it will never become overrun like St. Thomas. And both are stunningly beautiful.

    It struck me that none of the typical Carribbean vacation islands are on this list. But they do offer some great alternatives and some completely difference cultures. The British Virgin Islands are others I’d like to get to. Retiring there? I would have to see.

    by Rich — November 5, 2014

  3. In 2006, I took a cruise around the Hawaiian islands. I still recall that the tour bus drivers on both the big Island and Kauai said almost exactly the same thing: people visit the islands and are so swept away with their beauty and relaxed ambiance that they decide to retire there. Sometimes, they find a way to move there while they are still working.

    They almost always last about six months, then they move back to the mainland. They miss their families, and they don’t have much social life nor very many activities to engage in. They get bored quickly. Once you get outside of Honolulu, most of Hawaii shuts down at 6:00 and doesn’t have much going on.

    When you visit a place like Hawaii or a Caribbean island or most vacation spots, you’re probably staying in a nice hotel or condo and you spend your relatively short time there on the beach or discovering the other beautiful spots on the island. If you move there, you’re probably not going to be living in that nice resort and you will soon get tired of going to the beach every day.

    I’ve learned that most vacation destinations aren’t well suited to being good retirement choices, unless you plan to operate a tourist-centered business after you retire, such as a B&B, a tour service, or a gift shop.

    On my web site,, I also explore the issue of great places to retire, although certainly not with the thoroughness and depth that this web site offers. (My kudus, by the way!) I tend to recommend against island destinations for the same reasons that John (Admin) stated above.

    One island destination that stands out for me is the Canary Islands. The cost of living seems relatively low for an island, the climate is nearly ideal, and they are large enough and populated enough to provide the infrastructure and cultural and recreational amenities that would sustain day-to-day life. Of course, you would need to learn Spanish (if you don’t already speak it), and it would cost more to travel back to the U.S. for visits. On the other hand, you’re much closer to Europe! It’s on my short list of places to visit.

    by Dave Hughes — November 5, 2014

  4. After living on Jeju Island, South Korea I know island living is not for me. The food was crazy expensive and the heat and humidity in the summer (98 degrees and 90% plus humidity) was unbearable. I’m happily retired in Idaho!

    by Kathy — November 5, 2014

  5. Mount Desert Island off the coast of Maine is the ideal summer island. We had a summer home for many years on the island but sold it last year as part of our downsizing plan. The island is the highest point on the Eastern seaboard, so the views are amazing. There’s also Acadia National Park, which offers many opportunities for nature education, hiking, biking, etc. There are plenty of places to eat and things to do in the summer, and we contemplated moving there for retirement. But, and a big BUT, the island closes up after October, and the winters are long and cold. I had one islander tell me that they love it when the tourists go home. They’re plenty busy during the winter with snow shoeing and skiing in the park. You just have to like the cold, damp weather.

    by Carole — November 6, 2014

  6. I’ve lived on Hilton Head full time since 2005 and was a part-timer before that starting in 1993, spending several months every year during that period. When I built there in 1993, it was a beautiful, quiet area. Bluffton was a way to get to the island with few people, no lights and no traffic. The whole area has changed. It used to be busy in the summers only. Now people are here year round, and I can’t stand dealing with the tourists any more, so I’m moving to Tucson. Maybe there are lots of tourists there too, but not all crammed together. I will miss my friends, but we already have plans to get together. I plan on traveling to coastal areas on a regular basis. I think different places work for us in different stages of our lives.

    by Barbara — November 6, 2014

  7. This comment came in from Sam concerning the San Juan Islands mentioned in this article:

    There are many Islands on which to retire. So, why list the islands most likely not to be available???

    Try these for starters:
    Shaw Island Bainbridge Island
    Hartstein Island Shaw Island
    Orcas Island with a major State park and several major resorts
    San Juan Island which has a major medical care center
    Lopez Island
    Whidbey Island Which has major medical care in Coupeville and Oak Harbor
    Camano Island
    Vashon Island
    Maury Island
    Fidalgo Island with Major medical facilities
    Samish Island
    and lastly, Guemes Island a 10″ ferry ride from Anacortes

    All are here in the State of Washington mostly in the Salish Sea or Puget Sound. All support
    a laid back life style and are accessible by ferries or both land based and float plane based aircraft.

    There are also many islands accessible only by boat.
    Do not lose sight of the fact that Washington State has perhaps the Nation’s largest ferry fleet
    with connections to Black Ball Ferries, BC Ferries, and the Alaskan Marine Highway.
    No state income tax.

    by Admin — November 6, 2014

RSS feed for comments on this post. TrackBack URL

Leave a comment

Salary Data custom salary reports specific to your state and industry.