What Is the Ideal Way to Move to Hawaii?

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View of Windward Oahu

As we think about moving back to Hawaii, I’ve been considering how I want the process to go. I want the move to be smooth and with as little stress as possible. I’ve outlined on paper how I think the best way to go about it is, and now I’ll publish it here so you can have an idea what might work for you as you contemplate moving from the mainland USA to one of the Hawaiian Islands in the next year or so.


If money isn’t right, there’s no sense in moving. The ideal move to Hawaii in my mind can only be accomplished if the money is there. If it isn’t there yet, save more until you have what you need. There is nothing fun (at 40+ years of age now!) about scrounging for deals on everything that is needed for the move. Airfare? Sure, being thrifty can save you a couple hundred dollars in a few minutes of judicious searching online. Do it. As I’ve grown older I find it takes more out of me than it’s worth in money to be constantly searching for the cheapest of everything. It’s expensive for a reason – you get value from it, and sometimes it saves you some of life’s most precious commodities – Time. Time is worth everything. There is nothing that compares, right? Anyway, I strongly suggest that your finances be in order and that you can move to Hawaii without money being too much of an issue. Unless you’re young and still foolhardy – like most of us were when young – and you don’t mind spending a lot of time to search for things at a lower price.

What is the right amount of money to have before moving to Hawaii?

That’s a question for you, and you only. And then, most of us won’t be able to answer it with any accuracy. You can guess, and that’s the best most of us can do. Even having lived a few places in Hawaii, when I try to make an estimate of how much money the move will cost us – I just come up with a range. A lot depends on factors that I cannot control or guess correctly. How can you guess how quickly you’ll land a job you want, that pays what you want, so you don’t have to keep using your savings? Impossible, right? So, don’t beat yourself up over estimates, but, give it the best shot you can.

If your money isn’t right, the move to Hawaii also, isn’t right. Don’t push it, just work harder to save more money. Hawaii is worth the extra work, the extra effort, the extra time and thought to make the move across the Pacific Ocean as fluid and seamless as possible. Be careful not to underestimate the amount of cash you’ll need to bring with you for your move. This is a very common mistake. It’s crucial that you have enough.

Gross estimate for how much money someone from the mainland USA might need as a single twenty something with skills in an area that could help them land a job in Hawaii fairly fast?

$6,000 saved, and you should be ready to spend all of it. You should also have a Plan B in case it doesn’t work out at all. Plan B might involve having another $4,000 saved to return from whence you came, or to move to a new spot on the mainland.

Gross estimate for a family of four with one adult working?

$25,000 including a Plan B.

These are just numbers I’m pulling out of almost thin air. I think these are reasonable numbers for some people to be able to get their start and get up and running in Hawaii as the move from stateside. Actual figures might be far higher or somewhat lower. You really shouldn’t move without something like this amount of money saved.

So, part of the answer to the question about the ideal way to move to the islands, is your finances should be more than adequate to cover the move.


Kaneohe, OahuIf you’re not worried about employment, you have a pension or some work you do at home that pays the bills and that can keep paying the bills once you move to Hawaii, then that’s pretty ideal. Not having to think about, worry about, finding a job you like and that pays enough, is a major advantage for you and your move will be made easier by your situation.

Still, rent, food, transportation, insurance, and the rest of it is going to cost heaps of cash. You’ll need a nice chunk of money saved, and you’ll need to be absolutely sure your business can work from Hawaii. If your stay at home business requires fast and cheap shipping – Hawaii might not be the ideal place for you. Shipping costs and time to reach areas outside the islands are higher and longer than from the mainland, and many countries around the world.

The time it will take to get a job is another important consideration that requires a guess. I think most people greatly underestimate the time it will take to become employed.

Even the most hopeful, cheerful, and outgoing hopeful Hawaii residents write me a couple weeks after they’ve returned from Hawaii and tell me how difficult it was to land a job as a server, waitress, or some other entry-level position. Hawaii’s job market is very different from most places. Tourism runs the entire state. A certain type of person is needed as a greeter, a waiter, the manager of a hotel in the Islands. You may or may not be the right person for the job. I think personality is taken into account more than in other places because there are just so many people looking for entry-level jobs that employers can pick and choose those with the skills, but those with the extras too. The ideal waitress might be someone who has a couple years experience, no kids, a bubbly personality (talkative, friendly, and smiling), and friends who have lived on the island for a couple years. If you look like you’re addicted to something, if you’re late for work, if you’re moody, none of these things fly in Hawaii for entry-level jobs because the job pool is large to choose from. So, even entry-level jobs can be hard to land.

If you are qualified for some better job, there are likely others competing with you for the same position. There are many locals with jobs in the State, County, and Federal jobs that get their opportunity because they know someone working at the place already. This is a major factor in getting a job that you won’t be able to take advantage of for a while until you start to know some people. Many jobs go unannounced. Many go immediately to friends.

Local residents take care of each other, and look out for each other. It’s almost like a club. Your friends, everyone you know, but even people you don’t know that are locals, are looked out for. Employers would much rather hire a local resident for a job than someone just arriving off the plane and looking for a employment.

Why is that? Many reasons, but primarily it’s a matter of believing that locals with family on the island, will be more inclined to stay at a job for years, not leave in 6 months as they realize they can’t cope with living Hawaiian Style, like many recent arrivals.

Getting a job offer before you arrive on the islands and have a place to live, a Hawaii ID, a car, is not easily done. I nearly had an offer, but I had some specialized skills in IT that were desperately needed. Still, I didn’t get a job offer, despite having lived in the islands over the years multiple times. The company still wasn’t prepared to make an offer before I moved, and at the time I wasn’t ready to move before I got an offer. So, that fizzled out. I have heard of only a couple of people having an offer of a new job without having lived on-island first. Some other job seekers are able to transfer within their company to jobs in Hawaii. I’ve had a small number of people write me here at the website to tell me about these situations. Sounds pretty ideal, right?

So, finding employment in Hawaii is never as easy as you think it will be. You’re probably an optimistic person if you’re considering making the move. You’re probably saying to yourself, “Everything will work out!” And yes, maybe it will all work out, but please do be cautious about the two major considerations – money and employment. If you get those two things taken care of, the rest is easy. I think so anyway.


People are split on this, but here’s what I think is the best way to go about it.

Sell or put into storage everything you own at your current home. Don’t take anything with you to Hawaii when you move, but a week’s worth of clothes and your camera and phone.

Yes, you can ship anything over to Hawaii. I have even had people contact me that were shipping horses over to Maui from California. I think anything can be shipped, but I wouldn’t do it for 2 reasons:

1. You don’t know how long you’re going to be living in Hawaii. There are many reasons you could leave within weeks or months and have to ship all that stuff back to the mainland. Talk about a giant pain!

2. What you are accustomed to today, may change drastically as you move to the islands. Styles, preferences, your lifestyle itself may change dramatically. Rugs, couches, big dressers, etc., all of it may seem like an eyesore after you move to Hawaii and realize you don’t really need or want any or much of what you brought with you. Then if you try to sell it – nobody in Hawaii wants it either.

I strongly suggest you buy what you need in Hawaii. Don’t buy the best stuff in the world, but buy something to get you through a year. I think your preferences will change after a year living in the islands, and you can sell the stuff you bought as a stop-gap measure, and buy other things you really want.

I’ve shipped cars and some personal items to Hawaii before. With one car, I was glad I did so. With the other, not so glad. There are MANY used cars on the islands to buy for very good prices. There is a glut of supply of vehicles of all sorts on Oahu especially, but on any island you shouldn’t have a problem finding something you like for a very reasonable cost.

Your taste  in clothing is going to change. Unless you’re already running around in shorts and palm tree covered shirts, you’r taste is going to change. Don’t bring many clothes as you move. You’ll be happy you didn’t. Really. Even myself, I’m not very fashion conscious, and yet most of what I brought over to Hawaii in 2002 was not what I was wearing by the next year. I gave away bags and bags of clothes that I just had no need for anymore. I spent a lot of money on clothes that were very lightweight, cool, and comfortable. I suggest you buy your clothes in Hawaii after you arrive.

Ship your personal items over to Hawaii, or buy them when you arrive? I say buy them in Hawaii. Others will argue with me. Up to you really.


Kauai CanyonThough inside you are probably doing backflips over your amazing opportunity to move to one of the Hawaiian Islands, I hope you’ll adopt a “cautiously optimistic” attitude about your move. Exuberance tempered by reality. Something like that.

I think moving to Hawaii is primarily an emotional choice that we make. The allure of the place is magical and unstoppable for some of us. I can’t tell you the number of people that have written to me after their first visit and told me that they felt like they belonged in Hawaii. Mysteriously it does that to people. If you’re considering the move, you probably are emotional about it. You probably have put off concerns that are realistic and are ready to charge gung-ho into the moving process.

I’m excited for you, and yet I hope you look at the move realistically and definitely have a Plan B to fall back on in case things sour in paradise. I think most people moving to the islands for the first time return back to the mainland within 6 months. Definitely within a year, most people return. Those that stick it out are probably those that had a realistic idea what they were going to be facing once they arrived in Hawaii. It’s a fight to stay. There are many things you’ll need to surpass. Many problems you’ll need to find solutions to. Sometimes you’ll struggle with finances. Other times you’ll struggle with finding a better job or the right job, a higher paying job. You may struggle with not being able to live at the comfort level you were accustomed to back in the mainland.

There are so many areas of life that will change as you move to Hawaii for the first time. But, the good news is – there are people doing it successfully. People like you. People that have the chance to move, and take it, resolving all the little obstacles in the way and making the move to a place where dreams are made. Even the most simple life in Hawaii can be the ultimate way to live life. In fact, many people go this minimalist route as they move to Hawaii. Their car becomes a bicycle. Their house becomes a room they share in someone else’s house. Their 12 hour work days become 4 hours of part-time work, just enough to pay the bills and relax and enjoy surfing or reading books on the beach.

The ideal way to move to Hawaii is the way you make it happen. Strive for less stress. Strive to keep a balanced perspective and balance to your emotions and the reality of making the move. Think about sacrifices you will have to make, and accept them as part of the move. Look at moving as an opportunity to completely change your life because… your life will change dramatically!

Best of luck to you on your move! There are more than 150 articles here about life in Hawaii – here is the article index:

Hawaii Articles

I’ve been updating my Moving To Hawaii book series for years now. Here is the latest iteration:

Moving to Hawaii – The Good, Bad, and Uglyavailable at Amazon;

I have a forum at Facebook – Facebook.com/HawaiiForum – join here!

A couple years ago I did a series of free videos at Youtube. I reviewed the Moving To Hawaii book chapter by chapter and talked about what was covered – maybe interesting for you too. The first video is embedded below, the other videos are linked by number:

Moving to Hawaii Videos  234

Aloha and best of luck and life to you!

Peter Kay


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. James H 08/22/2017 at 7:35 am - Reply

    Just sold my house in Colorado, and my son started his first year at UH Manoa this Monday. Used to live on Kauai 20 years ago, and have been aching to get back. You CAN make it work on Oahu, just need to stick to a budget and adjust to having more friends and social activity than things. Things do not enrich your life. I spent half my life acquiring things, and now it’s time to acquire self and a better purpose.

    • Peter Kay 08/22/2017 at 9:16 am - Reply

      Well said! The material value component is one of several I used in the “Can I live in Hawaii” quiz to see whether people will have an easy or difficult transition to Hawaii. You definitely have to adjust to a qualitive vs. quantitive lifestyle.

  2. Cheri 08/17/2017 at 2:02 pm - Reply

    I’ve devised Oahu is the place for me ,, now to find a long term affordable rental of some sort , Not a house . And Not sharing a room , open to other options . Suggestions ???

  3. Helayna Dean 08/12/2017 at 12:55 am - Reply

    Wow, Reading this has definitely put so much of my thoughts into perspective, my family and I jst got back from a week long holiday in Oahu for my sisters 21st bday, and I jst completely fell in love with the island to the extreme point that I’m considering moving, Iv given myself two years to do it.. it’s my goal and it’s what I want so I’m sooo anxious to get my big move started, I agreed with everything you said and I’m gonna study and research everything I need to. Thank you for the advice and experience

  4. Annie N 05/23/2017 at 9:55 am - Reply

    My husband and I are considering our exit plan from Utah. We are strongly considering Maui, it is my favorite island, he has never been to any…. I lived on Oahu in my late teens – now in my 40’s. I have a great job that I can do anywhere. Our whole office be working remote in about a year. We have ample time to decide on where to live but feel that Maui will work best for us and what we want out of our lives. My only concern is moving and finding an issue with my work – if my employer is based on the mainland do they have to get licensed on HI and pay into any strange taxes? I ask because we moved to CA a couple years back for my husband’s job and after 6 months he couldn’t handle the commute and the job so we moved back to UT – we then found out that even though my company never conducted business in CA they had to pay a special tax just for my being there. If you know how the telecommuting is structured there it would be really helpful – I have been searching the internet trying to find information but have not been successful.

    • Peter Kay 05/23/2017 at 10:51 am - Reply

      Good question. I would start by looking up the Hawaii Department of Labor and asking them.

  5. Michelle 03/22/2016 at 1:59 pm - Reply

    I was just offered a job working for the state driving a recycle truck. I applied a year ago and they just got with me and interviewed me over the phone. I wanted to move there so bad but now I’m getting scared. I have a fiancé and 3 kids. Do you have any advice for me? We are thinking about selling everything and making the move.

  6. Rhonda 07/14/2014 at 3:17 am - Reply

    So glad I read this! “It’s a fight to stay” is what sticks in my head. As a person who once ended up living in her car for several weeks in Redwood City because I leaped and left the outcome to the good graces of God…. lol…. I appreciate the reality check! I’m on disability, so can’t actually work. But now I know I’ll have to be ready to go SIMPLE to afford to live there. Probably ready to do that anyway. I’m going for the weather, and the aloha way of life. Mahalo

    • Vern 07/14/2014 at 3:37 am - Reply

      Best of life to you Rhonda, I hope you make it work for you! Aloha, Vern

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