Retirement in Hawaii

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Dreamy Hawaii Beach at sunset

If you are considering Hawaii as a retirement destination you are not alone!

Many people reading my “Moving to Hawaii” ebook are sending me email to ask more questions about what it will take to retire in paradise. Unfortunately, I haven’t retired yet – so I don’t know many of the answers they are asking. What I do is tell them to find a realtor they trust, on the island they intend to move to. Realtors can help Hawaii retirees find homes to stay in, and also they have access to loads of other information about resources retirees can use once they arrive in the islands.

On thing I do know… Hawaii does not have any Certified Retirement Communities.

But, some cities and towns in Hawaii are very popular as retirement communities. I have met retired men and women living in Waikiki, though not many. If you stay in Waikiki you can walk to just about anywhere you’d need to go. Public transportation isn’t the greatest, but you could survive without a car if you had to. My car took a month to arrive so I bought a mountain bike and rode around town with that – even going as far as the airport one time.

One of the biggest considerations you’ll have when moving to Hawaii for retirement is your health insurance and coverage. Don’t just assume it will all take care of itself. Hawaii is a state, yes, but things – even things like health insurance – can require some insider knowledge to get all you can get out of it.

Here are some Pros and Cons of Moving to Hawaii as a retiree that may or may not fit your situation. Read them quickly and decide if any apply to you:

Cons of Retiring in Hawaii

1. Are you used to the good things in life? Foreign and independent movies? Do you run in the art scene? Do you like Saks and other high end shops, and endless shopping? Hawaii has some high end shops, for sure, and some unique items… but, Hawaii is not a shopping mecca for those that live here because the selection is limited. You might bore easily in Hawaii.
2. Are you frantic when you see a roach run across the floor? Ever see a gecko on your wall? Hawaii has both of these – and everyone has to deal with them… some more than others!
3. Can you handle being a minority? Some people have a hard time with this. Others can live in the country side surrounded by locals from another world. If you don’t get along well with people from other cultures you WON’T do well in Hawaii. Guaranteed.
4. It takes a lot of money to get off the island for a break – even inter-island, the cost is something to think about – it’s not like you can take a ferry to Maui for $40 from Oahu. Can you live for long periods of time in one place – on one island? Or, do you have the cash to spend to travel back to the mainland at $300 at pop?
5. Dating prospects are very limited. Friend opportunities are probably much more limited than in the mainland.Pros-


Pros of Retiring in Hawaii

1. Some retirees can land jobs doing something they love – in the place they love, this helps them afford all the extras they’ll likely want to spend money on once they move to Hawaii to retire.
2. The worst that can happen if you have a fall back plan? You return to where you came from. Don’t put all your retirement eggs in one basket when you move to Hawaii. See if you can go for a year and make it work. If not – no worries, it’s not the end of the world. There is still Florida, Mexico, Arizona?
3. Hawaii inspires creativity. I know three people that started writing books when they finally settled down in their new home.
4. A slower pace of life is evident in Hawaii – to nearly everyone. That alone is worth trying the move!
5. If you love boating, swimming in the ocean, surfing, snorkeling, running, walking, good food, and want to live your life in paradise – Hawaii has all this – and so much more beyond the basics.

Retiring in Hawaii need not just be a pipe-dream. You might be able to make it work. There is a lot of information on this site at the “Moving to Hawaii” link at the top of every page. If you’re considering moving to the islands and have any questions – feel free to leave any question for us in the comments section just below and we’ll do our best. We don’t know everything, but a lot of easy questions about moving to and retirement in Hawaii get answered when you leave them in the comments.

[Photo credit – member, paul (dex)]

About the Author:

I’ve lived Hawaii since the mid ‘80s when I moved here at the age of 21. I arrived site-unseen in Honolulu with zero contacts and about $5k in savings. I worked from nearly zero and today Hawaii has given me the greatest gifts in the world in all aspects: spiritually, financially, romantically (married since early ‘90s w/ 2 children), and most important, peace. My goal with this site is to share the magic of this Land of Aloha and help others who are on a similar quest.


  1. Linda Voigt 05/17/2018 at 2:45 pm - Reply

    Our problem is which island. We like Oahu, Maui. I like the Big Island but my husband is afraid of the vog. Does Kamuela get vog? I’m not sure how we will decide. Each has it’s own virtues. We can’t even decide where on Maui, we like a number of different places. Oahu is easy, we like Kaneohe. OK so my husband likes up high for the cool. We both like Kailua and Lanikai beaches a lot. Upcountry Maui. And of course there are no end of lovely beaches on Maui. Kamuela is cool and we love Spencer Beach. We are older and may need advanced health care at some point so a friend on Oahu says oh it has to be Oahu. Is that true? We like the culture and the people. But will they like us? Don’t want to be getting stink eye all the time.

    • Peter Kay 05/17/2018 at 9:17 pm - Reply

      If you are concerned about access to healthcare, Oahu is where you need to be. As far as getting along, I suggest you sign up for the newsletter and stay tuned for the program I’m launching to help people that are right for Hawaii.

  2. Mark 02/25/2017 at 3:54 pm - Reply

    I am retired with an annual net income of $48K/yr. I also a 401K and other investment income. No bills, other than a mortgage pmt. I also should have at least $100k equity in my current house. Thought about selling my house and purchasing a small house on the Big Island, either in Hilo or Kona. Do you think that amount would be enough to live comfortably?

  3. Kalono Kaumakapili 02/21/2017 at 9:13 pm - Reply

    Aloha Vern, I have grown up in Honolulu, and lived in Hawaii for most of my life. I currently reside in Hilo, Hawaii Island.
    Since building my home here 5 years ago, I have come to find that this is an ideal place to retire, not only for people from the mainland, but those from Honolulu.
    I found your website, and I must say that it is very well made, and informative. I am currently building my own website/blog ( to let people know that it can be affordable to retire here, provided that you know where to look, and who to look to for help. Also, to go off grid if they decided to go that route. I aspire to be that “go to” guy when people are contemplating on making their move. Someone who can prepare them BEFORE they move here, and then guide them thru the process of finding (or even building) a home for retirement, and be there for them after they are settled, and beyond…

    Your thoughts, greatly appreciated!


    BTW, who built your website? Terrific!

    • Peter Kay 02/22/2017 at 1:31 pm - Reply

      Aloha Kalono, I redesigned the website after I took over from Vern’s excellent stewardship. Good luck on your adventure and mahalo for the comments!

  4. Yvonne 01/27/2016 at 3:43 pm - Reply

    Do all the islands have Kaiser perm. insurance?

    • wayne 06/29/2016 at 9:12 am - Reply

      Moved here 25 yrs. ago from southern Cal.. Not much different in cost of living if you are on the Big Island. Great community in North Kohala.

    • wayne 06/29/2016 at 9:19 am - Reply

      West side of Big Island Just built new medical facility.

  5. Dinyar 04/23/2013 at 3:40 pm - Reply

    I find your website the most helpful. I am 66 years old retiree. I used to manage construction of high rise buildings in NYCity. My wife, originally from Philippines, is an RN at Memorial Sloan Cancer Center and will be taking an early retirement on September 1st. of this year.
    Our main concerns are- a) which town in the island of Oahu is best for someone like me with asthma, RA and OA. b) Are there good doctors and specialists available in Oahu?, c) my wife will be covered under my health insurance GHI and if that is acceptable there?( I will be covered under Medicare and GHI.)
    d) we would like to purchase a Single Family House. should we rent first? We will be selling our house her in NY.
    Can you recommend any Real Estate Agents?
    Any advice will be greatly appreciated.


  6. emily hinton 02/15/2013 at 10:59 am - Reply

    my husband and i are looking to move into a senior community in hawaii. we need help in finding the right place. can you give us a hand in finding the right place for us? we are both in our 70’s.,not all that active, but do not need help with everyday living. We would just like to enjoy getting out of the cold and not the upkeep of a big property. Any help would be welcome. Thank You

    • Vern 02/17/2013 at 7:49 pm - Reply

      Aloha, Which island Emily?

  7. Karen 01/07/2013 at 4:45 pm - Reply

    I retired in June. Although I live in a beautiful central California beach town (pismo beach) I am looking into possibly moving to the south of France, Ireland or now Hawaii. I lived on Oahu (Kaneohe) in the late 60’s & thought I would live there forever but had some bad things happen & came back to the Mainland after only a year & a half. My question is more about affordability. I am not in a place that I could purchase a home but I have an average pension.64,000 annually & wondering if that would be enough to live on over there. I remember even when I lived there that the cost of living was a lot more than here.

    Well…thanks for listening & hope to hear from you.

    • Vern 01/07/2013 at 5:26 pm - Reply

      I think you could live anywhere in Hawaii on that income. Your life would not be unpleasant! You could even save some every month… I think. I could anyway. lol. Hawaii has changed a bit, but overall – you’ll find it the same. The places that were full of people, buildings, are full of them now. The places that were parks and nice beaches – are probably the same. Best of luck and life to you… Aloha, Vern

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