Showcase Listing

Few towns in the Southeast offer more gracious charm than Aiken, South Carolina.  Take a relaxing stroll through Aiken's tree-lined ...

Showcase Listing

Bon Ayre is a 55+ active adult, manufactured home land lease community located in Smyrna, Delaware, a town which was recently ranked 31st...

Showcase Listing

Welcome to Cresswind Charlotte!  This nature-rich refuge of inviting streetscapes, manicured landscaping and miles of walking trails...

Showcase Listing

Cresswind Wesley Chapel is a vibrant, brand new 55+ active adult community Located just 40 minutes from Charlotte City Center.  Wesl...

Showcase Listing

Brookfield Residential at Two Rivers is a brand new community designed for those 55+, and offers an abundance of opportunities for a vibr...

Showcase Listing

Birchwood at Brambleton is an exciting new community for active adults 55+ located in the heart of Loudoun County, and is intentionally d...


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

  8. These comments were moved from different Blog – a better fit for more discussion:

    I cannot find a category for U. S. Virgin Island retirement or any information on what might be available for 55+ living. Anyone live there and if so can you tell us your experiences, cost of living, cost of housing and things to do?
    by louise — September 6, 2017 | Edit This

    I agree with Louise. The USVI are a great option as banking, legal, immigration, customs, etc. provide for an easy transition to island living so there needs to be a thread on this website covering the USVI in detail. St. John is very expensive since 2/3 of the island is a national park therefore can never be developed. St. Thomas is too touristy for me as the huge cruise ship port can sometimes have 6 ships docked at once during high cruise season. My wife and I are investigating St. Croix as after 2 vacations there in 2010 and 2017 we really enjoyed it and the real estate is dirt cheap.
    by Dan — September 7, 2017 | Edit This

    While the USVI are a beautiful, please note that major trauma may necessitate transport to Puerto Rico. While there may be a small hospital on either island, retirees may need f full fledged staffed hospital able to cope with any medical
    incident. Also, note that as an island most things are imported and are more expensive than in the U.S. When choosing a retirement area especially overseas, look at it from a locals view not as a vacationers view.
    by Tim O’Dwyer — September 7, 2017 | Edit This

    Dan, How about hurricanes? Any historical information on that in St. Croix?
    by louise — September 7, 2017 | Edit This

    by Jane at Topretirements — September 7, 2017

  9. TGIF Louise,

    My retirement plans include a small condo in a large USA hub airport city (Charlotte/American or Atlanta/Delta or Denver/United) in addition to our USVI (or Belize) primary condo so we may have access to major medical in the USA if the need arises. My wife and I are low maintenance DINK’s that choose not to have kids so we could instead max out our 401K’s and IRA’s savings from 25 years old onward. Therefore, we can maintain 2 modest condos instead of dealing with the issue of an all eggs in one basket relocation decision. If a hurricane is coming we simply fly to our USA condo so no worries if the Caribbean condo gets blown away.

    Regards, Dan

    by Dan — September 8, 2017

  10. I rarely write into discussions but always appreciate opinions other people’s life experiences. When I read the recent posts to this discussion topic and saw someone asking about retiring in the USVI’s, I felt I needed to chime in, because I am one of those that can speak well from experience.
    My husband and I moved to St Croix 15 years ago following a life-long desire to live in the Caribbean. He unexpectedly passed away in June 2015 and I have now relocated back to the mainland US. We thoroughly enjoyed all the years that we lived on St. Croix and I am thankful every day for having made the move and experienced life in paradise. St. Croix is unquestionably a beautiful place where you can enjoy great weather and lots of activities around the Caribbean Sea. It was a great experience.
    That being said, I could not recommend anyone retire there unless you have a greater than average retirement income. Although there are housing bargains there, the cost of living is extremely high. And the selection of goods is extremely limited. Guests that visited us throughout the years all suffered severe sticker shock when they made trips to the grocery stores. Electricity costs more than 50 cents per kwh, which is outrageously high. All goods cost at least 25% higher than stateside and usually double the cost.
    Now I need to address medical care. The sad state of medical care on the island is the prime reason I decided to leave. The hospital is literally falling apart. Medicare has been threatening to withdraw their accreditation for several years now and I truly believe it will happen soon. That means not being able to use Medicare for anything at the hospital. Countless physicians have fled the island. There is one cardiologist left and he won’t take any new patients. If you live there, you must purchase emergency evacuation insurance. And don’t plan on going to Puerto Rico. Puerto Rico used to have outstanding medical care, but their economy has crumbled and now they have very few physicians as well. The thought of a medical emergency became more and more frightening to me.
    The VI government is one of the most corrupt and inept that you will find anywhere. It rivals any third world country. The Virgin Island’s government is the largest employer on the island, which speaks volumes. The infrastructure is deteriorating at a rapid rate and the government does nothing about it.
    If you worry about hurricanes, the VI’s are in a very active hurricane zone. They have seen some extremely devastating hurricanes.
    Again, I will always cherish the years that I lived on St. Croix and am so very thankful my husband and I moved there before we were retirement age. But I could not, in good conscience, recommend it as a retirement destination unless you have the means to keep two homes, one stateside and one on St. Croix. The snowbird life is awesome if you can afford to do that.

    by Kathy — September 9, 2017

  11. Kathy,

    I agree with everything you stated about the negatives of living in the USVI but it should not deter folks from residing on an island at least in the earlier years of retirement and if they are healthy. You had 15 good years before moving back stateside so that is a pretty good run. The island doesn’t have to be the forever home but rather a transitional home where you live while healthy and then move back to the states once becoming decrepit and in need of diapers. Every Caribbean island has a 25% cost premium (currency adjusted) versus living on the mainland as items have to be barged in and most items are not manufactured/grown on island. Every island in the Caribbean has a lesser infrastructure than what is typically found in the USA (except perhaps Martinique) and the same could be stated about healthcare. The island life is not meant for those that want to shop at Macy’s weekly or what a possession filled life it is more for active and those content with outdoor pursuits in place of things. One of the best things about island living is the people. In the states if you live in a retirement community or just an area with a lot of old people ll they seem to do is complain/whine about their ailments whereas the people are much more positive acting and pleasant and generally more grateful for their circumstances that what I see when I am stateside.

    Regards, Dan

    by dan — September 10, 2017

  12. Kathy & Dan, Both of you have given good advice. We all take medical care for granted till we need it. Life on St. Croix sounds pretty nice but good hospitals and Dr.’s are important. No one knows when they will need care. Snow bird life might be the ticket!

    by louise — September 10, 2017

  13. This comment from Dan was moved here from a different Blog article:

    What about St. Croix in the USVI? It is definitely in the SEm is cheaper than sister islands St. Thomas and especially St. John. The real estate prices are cheap and many direct flights to USA to get back to the mainland when needed or for relatives to visit.

    by Jane at Topretirements — September 15, 2018

  14. This may seem like a dumb question, but if you ordered grocery items on line from Amazon, Costco as an example, to be shipped to St. Croix, would that help keep costs down as far a grocery items? I know you can’t get fresh produce but if you bought canned vegetables, canned tuna, canned chicken and other dehydrated foods would shipping be horribly expensive?

    by Louise — September 16, 2018

  15. Very good question Louise.

    Here are 3 links to help answer your freight cost questions.

    by Dan — September 17, 2018

  16. My brother lives on St. Thomas. There are grocery stores there, as there are on St. Croix. True, the selection isn’t the same as in mainland stores, but he’s lived there for going on 50 years and hasn’t starved yet.

    by Laney Humphrey — September 18, 2018

RSS feed for comments on this post. TrackBack URL

Leave a comment