My name is Jamaica Michaels and I moved to Maui on a whim 16 years ago. Lots of people do that, it seems. That’s why they peddle those t-shirts on Front Street in Lahaina that say “Sell everything–I’m never coming home!”

Someone, maybe you, manages to take a vacation here to soak up the sun, the beauty of the ever-changing ocean, and the majesty of the West Maui Mountains. Suddenly, the cubicle back in Des Moines, or the overheated house in Alberta, or the snow-covered used-car sales lot where you just know you won’t make a single sale when you get home–not so appealing. So, you leap.

My reason for moving to Maui was simple: I had skinny, bony feet and never wanted to wear real shoes again. My move to Maui itself was ill-conceived and even more poorly executed. I took everything sentimental and left all the practical stuff–because of course I could just replace it here–ha! (At that time you couIdn’t even buy silverware on Maui; I had to go to Oahu and bring it home on the plane). I shipped my car, because of course I was staying forever. No trial run, just bam! here I was.

You have to understand, this was not me. I’m a planner, a Details person. I’m an ASID licensed Interior Designer, and with that comes the ability to problem-solve and execute details in my sleep. But Maui had bewitched me: it was the last morning of my first cruise of the Hawaiian islands with my mom. The cruise ship was chugging toward Maui, our last stop, and I stumbled up on the deck at 5:45 am with a crook in my neck from the small bed, and in dire need of a gallon of coffee. Just then the apricot dawn was slowly turning to a turquoise sky and I could only stand transfixed at the sight of the sunrise cresting Haleakala and spilling over the West Maui mountains. I turned to my mom, said, “By the way, I’m moving here,” and that was that. I hadn’t even set foot on the island. Wise woman, she didn’t even argue, figuring, I guess, that there are worse places for her only daughter to end up and besides, she’d get a free place to stay in Hawaii.

In this blog I will be sharing with you what it’s really like to live on Maui. Not the picture postcard /movie trailer/ cue the music version, but the day-to-day reality. For the past 12 years I have worked as a concierge at a Maui hotel, and I’ve also built both a house and a business from scratch here, and I’ve pretty much seen it all. I live “Upcountry”, where regular, Maui people live, which is to say not at the beach, but at an elevation of 1,500 feet, at the base of Haleakala mountain. I have one man (former professional surfer Mike Turkington), one cat, two chickens and lots and lots of papaya trees, banana trees, lilikoi vines, oranges, herbs and tropical flowers. That’s “Talulah” the boss hen, that I’m holding in the photo at the top, and we get nice brown eggs every day:

Moving to Maui is like getting married for the first time while young and naive. It doesn’t matter how much you think you know, you’re never prepared. It doesn’t matter if you’ve had the trial run of other relationships, marriage is a capital “M” . Just like Maui.

I promise I will give it to you straight: all the glorious, messy details of what it means to live in “Paradise.”(“Tell them about the cockroaches–be sure to mention the cockroaches!” my niece who is visiting just insisted.) So yes, the cockroaches, the red dirt, the pitiless wind (“Every day is a bad hair day on Maui,” Mike’s Mom says every time she steps off the plane.) The sky-high prices of absolutely everything… and the work-arounds that those of us who live here come up with. But also the enchantment that each sunset works on us, and the utter joy of getting up almost every single day to blinding sunshine.

So if you want to move here, or just love visiting Maui, stop by this site and we’ll chat. Just remember, in Maui, all things being equal, your hair will always look like crud.

A hui hou! (til next time). If you’d like to subscribe to this blog, please click the “Follow” button on the right. I post about twice weekly.

Aloha, Jamaica
Some day your life will flash before your eyes. Make sure it’s worth watching.


Copyright Jamaica Michaels, 2011,2012,2013,2014,2015,2016. All rights reserved. May not be reblogged or reprinted without written permission of the author.

98 thoughts on “Home

  1. This sounds sort of like St. John. My daughter wants to move to St. John and work on a catamaran working for tourist. She was very observant to notice the hostess at the restaurant from the night before was working at the scuba shop the next day. She was a little shocked. When she asked a young just graduated student that just moved there if this was the norm he said yes. Everyone pretty much works two jobs just to make ends meet. Is this true in Maui?
    We love Maui, and one day I think it would be great to take the plunge, but nervous about the cost of living.

  2. Nice read, I just passed this onto a friend who was doing some research on that. And he actually bought me lunch since I found it for him smile Therefore let me rephrase that: Thanks for lunch!

  3. Many people work two jobs, but that’s because the one job alone is only minimum wage. Most jobs are in the tourist industry. So working people don’t get much beach time in, contrary to what they think when moving here.

  4. Nice blog 🙂 Nice intro to your journey to Maui. Would love to hear more about how you bought the land, how did you build your home? etc. It sounds like an amazing life.

    BTW I graduated from UH. I plan on moving back within 2 yrs 🙂

  5. So glad I found your blog! Just returned two weeks ago from my one week vacation in Maui and I’ve fallen in love. I’m intrigued to read more. All advice is welcomed!

    Great blog!

  6. Good blog! I really love how it is simple on my eyes and the data are well written. I am wondering how I might be notified when a new post has been made. I have subscribed to your feed which must do the trick! Have a great day!

  7. Hey There. I found your blog using msn. This is an extremely well written article. I’ll make sure to bookmark it and come back to read more of your useful information. Thanks for the post. I will definitely comeback.

  8. Mahalo nui loa for this blog! It’s one of the best I’ve seen on daily life on Maui. Your writing has really driven the factors involved in day-to-day living on The Valley Isle home. I appreciate your insight and the generosity you’ve displayed in sharing your experiences.

  9. First off I want to say excellent blog! I had a quick question that I’d like to ask if you don’t mind. I was interested to find out how you center yourself and clear your head prior to writing. I’ve had difficulty clearing my mind in getting my ideas out. I do enjoy writing but it just seems like the first 10 to 15 minutes are usually wasted just trying to figure out how to begin. Any recommendations or tips? Kudos!

    • Aloha Jennine,
      I have been writing for so many years…and keep regular writing hours every day. BUT I was given a good piece of advice years ago that can help if you’re having trouble clearing your mind. Take a piece of writing, by either one of your favorite writers, or someone who writes in the style you are working in for your piece. Now, take 5-10 minutes and just type their words. By doing this, you get into the rhythm of THEIR writing, which gets you into the rhythm of writing, period. It helps you define that writer’s voice, which in turn will help you hear and filter out your own voice. It’s an interesting exercise. If you try it, let me know what you think!
      Aloha, Jamaica

  10. I’ve applied for some job openings in Maui. Visited there 4 years ago, loved it, dreams of retiring there someday. Then our lives changed this year, my fiancee lost his job, and mine is changing and I have to find a job with them in a different city. On a whim I applied for some jobs there. We will see. Que sarai, sarai ( hope that’s how you spell it! lol) I’m wondering about the “reality” of living there and came across your blog.

  11. My bf and I are planning to move to Maui in June. We both spent years in Destin, FL (also known as a drinking town with a fishing problem.) A couple of years ago, we moved to St Thomas (a drinking town with a sailing problem) which is where we will be coming from. Many of the things you blog about could be said of the Virgin Islands, as well. I am looking forward to actually living in the States again. Gas, groceries, and electricity are insanely expensive here. I just can’t believe that they could be even more expnsive there.
    I’m looking forward to reading more of your posts.

  12. Hi there! I, along with a million others, would love to move to Maui. My boyfriend has lived there twice, and loved it. But, we have two kids. 16 and 3. I have heard nothing but negative things about the schools there. My 16 yr old is really concerned about getting beat up by the locals. Is it really that bad?? By the way, he is a very polite and respectful kid…

    • Aloha Traci,
      If people can afford it, they put their kids in private school, such as Seabury Hall upcountry. This, of course, is very expensive.

      I’ve probably heard all the same stories that you have. Would you consider waiting to move till after the kids are out of school?

      Aloha, Jamaica

  13. Aloha! So glad to come across your blog. I’m not looking for the blog that promotes Maui so much as I am looking for an insiders viewpoint of living on Maui. I have a desire to live there, but can’t just up and go. I do need to plan and research. I am a teacher and currently live in Minnesota. I have gone through the process of attaining my Hawaii teaching License and have applied at several of the private schools. I am married and have 2 children (16 and 12). We are certainly not rich so the cost of living concerns me. Right now I have the mindset that I need to get a good job before I make the leap. We are all very excited, but I need to make sure I take the rose colored glasses off and try to get a good realistic idea of what to expect so I will be following you and leading from you! Thanks for sharing your thoughts on Maui life with us;)

  14. I am thinking about taking a job in Maui…. However I hate bugs!!!! Especially cockroaches . Perhaps thus is not the place for me. Perhaps you can tell me…. Are they in the plumbing?

    • Aloha! There is a belief that the centipedes come up through the drains in the house. A friend of mine plugs her drains at night before she goes to bed. The cockroaches crawl and fly. Some of it depends on where you live. For instance, our neighbor has centipedes in her house all the time, but we have only had six or so in all the years we have lived here. If you don’t mind the chemicals, Terminex can be a solution. We don’t use chemicals on our property at all.
      Best of luck to you as you make your decision. Thanks so much for reading along!

      Aloha, Jamaica

  15. You’re so interesting! I don’t think I’ve read a single thing like that before. So nice to find another person with unique thoughts on this topic. Seriously.. many thanks for starting this up. This website is something that is needed on the web, someone with a little originality!

  16. Aloha Jamaica from The Kingdom of The Zulus, KwaZulu – Natal, South Africa

    I return to Maui end of March to spend some time once again on its shores. I was on Molokai in October on a Kapua Mana training and then spent November on Maui.
    Thank you for your writings.
    It is so good to breathe the every day routines and rhythms of what it is like to be a resident of Maui.

    Have a beautiful day.
    Bernadette Jackson

    • Aloha Bernadette,
      What a lovely way to put it! Thank you so much for sharing. I’m so glad you are enjoying the blog,
      and I hope you really enjoy your time again on Maui…
      Much Aloha, Jamaica

  17. New here and wanted to say this is the best example of what it is really like to live on Maui, warts and all. I spend too much time dreaming of living there, and it is good to hear the reality of everyday life. Thank you!

    • Aloha, Michael!
      Thank you for weighing in…so glad you enjoy the blog. I really try to present a fair picture of Maui; as one reader put it, I “tell the truth without being discouraging.” So that is my goal, I guess.
      Thank you for commenting, and for being a reader. Please keep the comments coming!
      Aloha, Jamaica

  18. Can’t stop reading all your posts. I’m only 21 and I definitely feel like Maui is where my heart is. Doing my best to find out how possible it would be for me to up and move there all by myself. As crazy as that sounds. I feel like I would do anything to do so!

    • Aloha Porscha,
      So nice to hear from you…I’m glad you are enjoying the posts! It’s people like you who keep me writing.

      Have you gone to school? Do you have marketable skills? Is Maui a possible reality… If not now, then down the road?

      I wish you all the best! Keep me posted on how things are going, and if you have specific questions, let me know.

      Warm Aloha, Jamaica

    • Aloha Kristin,
      Glad you found the blog! I hope you have a speedy recovery from your surgery. I, too, was a concierge on Maui for years, and I loved it.
      Mahalo for reading along….best of luck with your blog!
      Aloha, Jamaica

  19. Had an excellent cruise with Turk tonight. Thanks for sharing him! Looking forward to following your blog! Aloha. Ray & Diane from Iowa.

  20. Hey! This is my first visit to your blog! We are a collection of volunteers and starting
    a new project in a community in the same niche. Your
    blog provided us valuable information to work on. You have done a marvellous job!

  21. Will be moving this Dec. Can’t wait. Never been but need a change. Any advice is much appreciated. Can’t wait for the adventure to start. Just about have everything here in Texas sold. Love the blog.

    • Aloha Jenna,
      Thank you for writing… I’m so glad you enjoy the blog. The move is exhilarating and mind-boggling all at the same time. I’m so glad you’re pursuing your dream! Be sure to read “Moving to Maui FAQ’s” and let me know if you have other questions.

      Thanks for reading along!

      Aloha, Jamaica

  22. Aloha Jamaica!
    My name is Rebecca and wanted to say thank you for your blog. I just recently visited my best friend in Maui and I fell in love! I’ve lived in California my whole life and have been working as a designer in the corporate world for 12 years now. I’m 32, single and no children. I do have a small dog Cody ( thank god for him! ) I’m def feeling like a change has got to happen for me, I sometimes feel like a caged bird living here on the mainland. I visited Maui and a whole new world opened up for me. I felt like I finally found a place where I belonged. I’m a free spirit at heart:)

    What would your advice be on finding a sustainable job? I know u said u also have a background in design. I’m willing to do anything even if it’s not in design just to have a chance for a change:)Thanks again for your words of wisdom! I find myself wanting to take the leap even more so now:)

    • Aloha Rebecca,
      Thank you for writing. I certainly understand your drive to leave the mainland… I just couldn’t wait to move to Maui! However, a job magically fell in my lap right away, and that is not most people’s experience. Also, I started my own design business as I had been doing on the mainland, and I was just amazed at how hard it was here. It takes forever to get anything, the shipping is insane, and the clients all complain about the prices, no matter how wealthy they are.

      If you’ve been doing corporate design, you might look into working with a company like Pacific Rim or Goodfellow Brothers. However, most of the old-time designers who’ve been here 25 years or more have the jobs sewn up. You also might look into working for one of those designers, especially if you are ASID. Sadly, the most you might get is a job in a furniture store, which I also did as a designer, for a while. What job does your friend do, who you just stayed with? Can she open any doors for you?
      A blog reader who was thinking of moving to Maui just came and stayed here for about six weeks with a month-to-month lease. She looked into the job market and deduced that everyone in the hotels was waiting to move up into the next position, so there would be no openings. She went home discouraged about both the job market and the month-to-month rental market.

      Readers tell me they are glad I tell them the truth and don’t sugarcoat it. So I wish you the best of luck….remember, it’s easier if you have a friend or relative already living here, which you do!

      Keep me posted on how things work out for you, Rebecca.

      Warm aloha, Jamaica

  23. Greetings from Minnesota! My husband and I are retired and have been offered a position managing a condo complex on Maui. We are seriously considering this. I am a horseback rider and wonder if there are alot of riders om the island. Also is it hard to mske friends if you are an “outsider”. We are excited about a new adventure. Thanks for answering!

    • Aloha Patricia,
      Mahalo for writing. What a great opportunity for you.
      I know there is a polo club Upcountry, which of course is where all the horses are! I had a friend who owned a horse, and she complained that it was very expensive to feed and board one on Maui… kind of like how expensive it is to feed and board a human on Maui, also.
      As far as getting to know people, I know for a fact that you’re in luck, because there is a strong contingency from Minnesota here. They meet at least once a year, and I believe there are “hot dishes” involved! Try googling the group and see what you find.
      I would definitely suggest you take a trip 🙂 and check everything out on Maui before you commit.
      I wish you the very best of luck! Let me know how it goes…
      Warm Aloha, Jamaica

  24. Jamaica,
    I’m very glad I found your blog. My wife and I are planning a move to Maui after I retire in 2016. We currently live in the Dallas- Ft. Worth metroplex but we don’t plan on staying here. We went to Maui in 2011 for our 30th wedding anniversary. I had been to Maui as a teenager but my wife had never been there before. As soon as we returned to Texas we began planning our next trip. In May of 2013 we returned and the pull got stronger. As the airplane was rolling down the runway to go home, my wife was crying like a baby. I asked her what was wrong. She said, “Promise me we’ll come back.” I said we’ll be back in two years. After we got home I was starting to do some retirement planning. We had thought about moving to Albuquerque or Santa Fe. I said kind of as a joke, since we’re planning on moving west, why don’t we go a little further west and move to Maui? Well, then we were off to the races. We’ve been researching and planning ever since. We’re returning to Maui next May to spend a week living like “locals”. We’ve rented a condo in Kihei and instead of eating out, we’ll be buying food at Costco or the local supermarket to get a handle on just what it will cost to live there. We’ll be looking for different areas where me might like to live and my wife will be scouting for possible job opportunities. She’s a retail manager here in Texas. Excuse my long windedness but sometimes this move takes us from joy to abject terror. We loook forward to following your blog to find out what this move and living on Maui is really like.
    Aloha and Mahalo,
    Mike Wilkshire

    • Aloha Mike,
      Thank you for sharing. I certainly understand the abject terror and joy thing. I was in that same position before I moved here. If it is truly a dream, and people have enough resources to back them up, I think trying Maui is a wonderful experience. Some come and never leave. Others last only a short while, but either way it is a treasured experience.
      Keep me posted on your progress. So glad you found the blog. Could you share what your search terms were that led you to the blog? Mahalo.
      Aloha to you and the Mrs.

      • Jamaica,
        I want to say that I did a search for “Living on Maui” or “Moving to Maui”. We’re trying to gather as much information as we can. We’re very well aware that living there,(or anywhere) is not the same as being on vacation. We’re committed to doing this but if it doesn’t work out we’ll treat it as an extended vacation and return to the mainland. We just didn’t want to look across the dinner table 10 years from now and say Why didn’t we at least try? We’re not planning on bringing a lot of things with us, just necessities to get started. We’re already Costco members so that should help. We’ll keep following your blog to pick up valuable info along the way.
        Mike and Rebecca Wilkshire

  25. Hi there! I was online searching for some real information on what it’s like to live in Maui. We to vacation and never wanted to leave, meeting several people who have done the same. We have to children who are eight and nine and we decided we want to go out and printed venture and moved to Maui for at least one planned year maybe forever but we wantedto do a trial period-or at least tell our friends and family that. I appreciate your blog and any thing else you have to share. I am a nurse and found some available jobs, my husband is meeting with someone with a job opportunity next week and then we may be putting our house here in shriveled up California for rent and saying Aloha to a brand new life. Do you have and advise or suggestions or warnings? I would love to know or talk with at least one person before we make the leap 🙂

    • Aloha Angie,
      I believe the smartest thing you can do is just what you said– rent out your house. Some people take to Maui like a duck to water, while others leave screaming after just a few months. It’s not for everybody. But if you do all of your homework, have jobs lined up, and hang onto your house in case it doesn’t work out, I think it would be an amazing adventure for you and your family.
      Let me know how things are going, and if you have specific questions beyond my Page “FAQs on Moving to Maui”, I will try to answer them.

      Thanks for taking the time to write… I wish you the very best of luck and much Aloha!


  26. Your blog is very informative. Like many of your readers; I am also considering a move to Maui. There will surely be jobs for me as I work in the Hospitality Industry and my husband is in IT and can work anywhere, just as long as there is reliable internet. My question is the school system, specifically Special Education. I have a teenage son that has special needs and is in a Special Education program at our current school district. Do you have any idea how the Special Ed System in Hawaii and specifically Maui compares to schools in the mainland?

    • Aloha Joanne,
      I have put your question to my friend who is a special education teacher here. I will get back to you with her reply. Thanks so much for writing! Aloha, Jamaica

      • Well, I am here! Living and working in Lahaina and loving it! The family and the dog will follow by mid-March. At this point we are still looking at living in West Maui, which means that my son will probably go to Lahainaluna. I’ve contacted the school district and so far they are very accommodting and working out all of my son’s special needs once he is here and enrolled in school.

        The whole purpose of moving to Maui is to give my son the benefits of a more laid back and small town atmosphere. We are certain that he will thrive here in Maui.

        Your blog is so inspiring to me! Thanks so much!

      • Aloha Joanne,
        So glad to hear you’ve made it to Maui. Please keep me posted on all of your progress. Sounds like you are making strides with the school system for your son’s needs. I wish you all the best with everything. Are you currently renting month to month? Looking for work?
        Congratulations! You will be an inspiration to everyone who wishes they could do it.
        Aloha, Jamaica

  27. Okay… It’s official… One-way ticket to Maui (check), hotel til I find a place to stay (check), FREAKING OUT (check)!! I’ll be arriving to start my new chapter January 6, 2015. Can’t wait to see what exciting opportunities and adventures Maui has in store. Wish me luck. Again, love your blog and travel tips always welcome!!


    • Aloha Jenna,
      Congratulations! Now, breathe….it will be all right. Have you found a job, or plan to look when you arrive?
      Keep me posted on how things are going. Have a great flight, and enjoy the holidays where you are.
      Aloha, Jamaica

  28. Hey there Jamaica,
    My name is susan..and im a 62 year old young at heart and spirit woman moving to maui in Feb. Like you..I’m doing it on a whim..well..not quite. My daughter has been living and working in lahaina for 7 years..she’s a boat captain. She asked me to consider being close to her..so I sold my ranch, horses, truck and trailer and most of my belongings..(sent one 7x7x4 ft pallet to maui last month.).So it’s real for me..and I’m waiting for the 120 day quarantine period to end so I can bring my dogs.
    I am frugal, eat healthy, live healthy..and love new adventures. I am hoping to meet like minded folks and enjoy what life has to offer. I hope to meet people around my own age to hike, bike, swim, kayak, or canoe with..I also love to ride horses and understand that upcountry is where the cowboys are..I have not picked an area to live but I’m thinking wialuku or kiehi might work..any suggestions ? will want to rent for a year or so..small is good..but Im not sure about the condo scene..kinda like some grass under my feet. Will keep in touch..thanks for your site.

    • Aloha Susan,
      Brave woman! That is a huge move. Do you mind sharing which boat your daughter works on? Mike and I were wondering… So, it’s a whole new life for you. I send you lots of good thoughts and hope you find the perfect spot to live. It sounds like an Ohana on someone’s property might be the ticket for you, rather than a condo. We have a senior woman living in our Ohana, she is very quiet and respectful and we love having her here. It’s usually quieter and cooler Upcountry. Wailuku can get foggy in the afternoons. Kihei is near the beach but gets a little crowded.
      Good luck and please keep us all posted!
      Aloha, Jamaica

      • Hi Jamaica,
        My daughter works for UFO Parasailing as well as for two other companies. One does whale watching out of Lahaina Harbor on Zodiacs and then she also crews for a fishing boat and Scotch Mist, She loves her work and co workers.
        Anyway, I think the Ohana idea is right on. I look on Craigslist daily..and I am visualizing what I want to find…I do like the idea of upcountry because I have lived on acreage on the mainland..and like a little space around me..Also, I love to ride horses and want to find a place I can ride. Not sure I want to buy a horse on the island…not sure about equine vets, farriers, and the issues horses may have on the island. I found one place that leases horses..,and I’m thinking that will be the way to go to start with. I think the North Shore will be too windy..but I’m open for anything..suggestions are welcomed.:)
        SO…where can I meet people my age? I checked on line for meet up group..any other ideas?
        Are you still working as a concierge? I would like to work part time…I’m very friendly and pretty smart according to my friends and degrees I have earned..My daughter thought I would be a good concierge.
        I’m sending my vehicle instead of purchasing one on the island..any comments about that?
        Thanks for the info you share.

      • Aloha Susan,
        I still think that volunterring is the best way for you to meet people. You could also volunterr to be an usher at the MACC and get to see the shows as well as meet fellow ushers.
        My friend who had a horse here was floored at the cost of feed when she got here. So ask lots of questions.
        I think that sending the vehicle is a good idea. I always go with the Devil you know, versus the devil you don’t! At least you know your own car.
        Will you rent when you first get here, or stay with your daughter? Speaking of your daughter, you mentioned she crews for Scotch Mist, so Capt. Mike would like to know who she is!
        Much Aloha, Jamaica

      • Hi Jamaica. Happy New Year. My daughter’s name is Lydia. I will be staying with her unless she finds an ohana for me. I just got a call from the school district and I have an interview on Jan. 13th. Wish me luck. If I get the job I would like to live in the Makawao area because the job will be in Pukalani. I hope I’m spelling the city names correctly. Im a newbie at this.:). My arrival will be Feb 17th. Arriving with two dogs. If you know about fleas and ticks..let me know..

      • Aloha Susan,
        Good luck with your interview TODAY! Let me know how it goes.
        Yes, you will need Frontline for fleas and something for the ticks. There was a dog in our neighborhood always covered in ticks and I felt so bad for her. Bad owners.
        Hope you find the ohana of your dreams to live in!
        Aloha, Jamaica

  29. Hello,
    Reading your blog has been interesting. My car is on it’s way to Maui, and I have a one-way ticket leaving on the 20th. Plan on camping until I find a place to live. I retired about six years ago at an early age 55, from the Baltimore/Washington area, and have been moving from place to place (Seattle, Juneau, San Antonio, Manchester NH, Key West, Las Vegas, now again Seattle), since then. So, pulling up stakes, selling everything, and moving has become the norm. Look forward to reading you blog, as I get ready to leave Seattle. Question: Do you think it is practical to camp while looking for a place to live? I want to explore the entire island before I decide where I want to settle down….do you have any recommendations of where to live. I am used to camping across the country while looking for a place, so I have done this before. I have backpacked thru Europe several times, so going with only the bare necessities is something I am used to. I am a planner and I usually drive my self crazy planning everything out step by step. If you want to make God laugh, tell him your plans….
    Look forward to hearing from you.


    • Aloha Chad,
      I thoroughly agree…if you want to make God laugh, tell him your plans. So, your car is on its way to Maui. Brave guy!! As far as camping around the island, your choices will be: camping at two spots in Hana…. Wainapanapa State Park which requires a permit, and a small camp ground near the seven sacred pools in Hana. Go early, it can get cery crowded because it’s small.

      There is also camping at Polipoli State Park Upcountry, which also requires a permit. And there is camping at Kanaha beach in Kahului which requires a permit.

      There used to be a campground on the West side above Kaanapali, but it got bought by a private party. Unfortunately, there is no camping anywhere on the west side other than a tiny strip of land along the highway on the way into Lahaina. Not really what you’d call a campground, but people do pitch tents there.

      I wish you the evry best. Let me know if you have other questions as you try out different areas of the island. If you get tired of camping, I suggest you google vacation-rentals to try living in places like Kihei and Haiku on a month-to-month rental basis. Good way to find out where it’s too rainy or windy or foggy for your tastes.

      Aloha! Jamaica

  30. i am retiring in 3-4 years and plan to move to Maui. I want to find a long term rental, maybe a condo, maybe in Kihei area to be closer to hospital, etc vs Lahaina area.. Any suggestions on how to go about finding rentals?? Also how do you check into shipping a car?? Thanks!! Love your blog!!

    • Aloha Jan,
      Thanks for writing. For shipping your car, check with Horizon Lines and Hawaii Car Transport. Be prepared to have to pay for a rental… I have heard stories of delays and the last time we shipped a car they “lost” it for a week… Sent it to the wrong port!
      Rentals are a bit trickier. Landlords want to know you have been here for at least six months, and are employed. So the retirement thing could be an issue. I always suggest people rent a short-term vacation rental and look for a long-term rental while staying there. You can also come on vacation, stay at a hotel, and try to go meet landlords advertising in the paper or on craigslist while you’re here.
      Good Luck with your move!
      Aloha, Jamaica

      • Hello Jamaica I love your blog about living life in Hawaii. My husband and I visited Maui two years ago for his birthday and with stayed for 6 days in wailea. Every since with left Hawaii with have missed it. My husband works for a escrow office here in San francisco and he is the one who makes more money than I do, he recently got a job offer to take over another desk, so he will be taking over clients from another escrow office in Maui. I work for the st Regis re hotel here and I might probably be able to transfer to another Starwood hotel or maybe see if I could work for the four seasons there. I also have my business here in the Bay Area as a florist for weddings and events. What do you recommend for me to do if with move to Hawaii? I was thinking if I get the job in any hotel that I could start on my wedding business in Maui and talk to people go to hotels and offer my floral design services to then for their clients and the hotel. As for moving with were thinking of renting for one year and buy a house later on. Any information would help a lot. Thanks for your help and the information on your blog!!

      • Aloha,
        I commend your desire to start a wedding floral business once you are here. I would definitely research the competition, which can be very stiff on Maui… Everyone is competing for those same dollars. So I would shoot for a solid job at a hotel first…a transfer would be great, and a very smart move.
        Get all your ducks in a row before starting a business. Research the GE (General Excise) tax which can be very time-consuming as a business person in Hawaii.
        I think it’s a very good idea to rent before you buy. See my FAQs on moving to Maui, that should answer some of your questions.

        I wish you all the best!
        Aloha, Jamaica

  31. Hi! i read your homepage and saw that you listed Des Moines, Im from Iowa so this caught my interest. Im graduated now and its always been my dream to move out to Hawaii and Maui. I was wondering, where would you consider the best place for a young male to live on the island? Ive started a little research and I’ve been looking but seeing as you have lived there for a while, you know what to expect. I am very eager and wanting to just move out there already!
    Looking forward to your response, thank you and Aloha.

    • Aloha Jarrett,
      Glad you found the blog! I would decide what you think you want to do for work, and that will determine where you live. For instance, to be a deckhand or boat captain, that would make you lean toward living in Lahaina or near Maalaea harbor. Same with being a waiter, cook, front desk person, or anything to do with the hotel industry. Not that people don’t commute from other parts of the island, but most young people want to be near the beaches. So that’s the Westside (Lahaina, Kaanapali, Napili) and the Southside (Kihei and Wailea). Be sure to read my FAQ’s on moving to Maui if you haven’t already…that should answer a lot of questions.
      Best of luck, and keep me posted on what you decide to do!
      Aloha, Jamaica

  32. Aloha, Jamaica! My boyfriend & I just returned from our Maui vacation yesterday. I started reading your blog in the airport & am loving it! Mike recommended it to us on the Scotch Mist sunset sail last week. We just bought a San Juan 7.7 & are learning to sail. We loved meeting Mike & enjoyed hearing his stories! Our dream is to move somewhere tropical when we retire, or live on a boat & call many places home. Your blog has already given me a feel for what island life is like – you have such a gift for writing. I’m looking forward to reading all your posts! Thank you for so openly sharing your day to day experiences! In one blog you mentioned missing certain things from the mainland. If you ever want something shipped to you just let me know, I would be more than happy to help you out! 🙂

    • Aloha Kat,
      So glad you’ve enjoyed the blog! I wrote to ask for more info about what herbs you gave your ailing kitty. Did you get that email?
      Thank you for writing!
      Aloha, Jamaica

  33. I am really enjoying your blog. Thank you for sharing with all of us. I love Maui and have been there many times over the years. What I aspire to is living there 3-4 months out of the year over 2-3 visits. have you heard of others doing this and what are some of the ways they approach housing. Thanks again

  34. Heading over In 2 weeks!! Planning to explore the island this time and see what’re I would prefer to live if I decide to move there!! Love Maui! All of your info is so helpful!! Aloha!

    • Aloha Jan,
      Thanks for writing. Hope you find your dream spot on Maui as you check out the island this time. Glad you find the blog info useful!
      Aloha, Jamaica

  35. Thank you for your words here …
    I’m inspired and befuddled a bit about the events of the last few years — I wrote a memoir about my Polush family and since its release I have been in a curious state… A former acupuncturist sent an email — would I like to housesit in Maui for three months … I laughed I cried
    Not sure why
    I arrive on June 29 and will be in Lower Kula! I’ve spent the last 15 years “getting ahead / trying to get ahead professionally … Much of it magical , and yet something shifted w/ the book — ancestral things , who knows … What I do know is that Maui fell into my lap, that I knew I had to say yes even though it defied reason. I have never been…
    Plus: my newspaper / publishing work halted and the person In me who grew up in the Midwest is saying: get a “job”…
    But my spirit seems to want me In Maui .. Or the other way around
    In any case … I’ve rambled … Thank you for your blog … I appreciate your insights …
    Greg Archer

    • Aloha Greg,
      Many people seem to find that “their spirit wants them in Maui.” This magical island has a starnge pull that can completely bewitch and befuddle people…so what you are experiencing is entirely normal! Lucky you to be able to housesit on the island.
      Enjoy your time here! Thanks for sharing.
      Aloha, Jamaica

  36. Aloha Alan,
    I am not familiar with Ubox, just PODS. I assume it’s similar?
    People in Hawaii moving to the mainland hire Matson Shipping. So you could price out renting a moving truck to a West cost port, then call Matson 1-800-462-8766 http://www.matson.com and price out a 20ft. or 40ft. container to get it across the ocean. Note that you have to hire a separate trucker to pick up and deliver the Matson container, which also adds to the cost.
    To me, your way sounds cheaper. Let me know if you have other questions…and good luck!!
    Aloha, Jamaica

  37. Havn’t heard from you for a while. Hope eveything is ok. Love the blog. Visit every February. Stay on the beach in S. Kihei. Honeymooned at Sheriton Maui in 1967. Back ever since. Let us know whats up. Best to you & Mike. Aloha, L

  38. I’m so excited to start reading your blog! We’ve been talking for 10years about moving to Maui (our favorite place to vacation) but lately we’ve been getting more serious about it. I laughed out loud when I read about your hair looking like crud every day! So true! But my skin always looks amazing there so I’ll take that trade 🙂 Thanks for sharing!

    • Aloha,
      Yes, you are right, your skin will look amazing in Hawaii (till the sun damage sets in! 😩) and yes, it is a good trade-off.
      So glad you found the blog and are enjoying it.
      Aloha, Jamaica

  39. Aloha,
    I too am no stranger to Maui and have one foot in the door owning 2 – vacation condos in Kihei. Of course they’re vacation homes to others most of the time. A friend who’d like to retire in Maui turned me onto your blog and I’m interested to read your experiences as I hope they will soon be mine…permanently.
    Very Best, Eilene

    • Aloha Eilene,
      I certainly hope that Maui can become your permanent home if that is your heart’s desire. Would one of those vacation condos in Kihei be where you would live?
      Aloha, Jamaica

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