Moving to Maui (Follow-up)

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Here’s a follow-up email to a response I gave a woman I called “Jen” at this post: Couple Thinking of Moving to Islands from Connecticut

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Peter you’re awesome! thanks!

I talked it over with my husband and we are truly leaning toward Maui. “Maui No Ka Oi!” right?! It feels a little surreal that this is even a topic of conversation. I mean, who WOULDNT want to move to hawaii?? But it’s a lot of work and it’s not easy–nothing worth having ever is. And I’m not naive thinking that all my problems will be solved if we move there but I do think I’ll have a better quality of life, even thinking about it gives me peace and a sense of relief and excitement all at once. We have been doing a lot of research about shipping the car and the dog and the quarantine. I’m a little worried about kona being on a plane for that long but hopefully he’ll only have to do it once. Here is our plan, let me know what you think…

I am planning on buying a ticket for the end of May (of this year) I went on the Hawaiian Air website and it looks pretty affordable for a one way $370-$480, but then it jumps to $600+ in June and then comes back down at the end of August. Jason will stay in Connecticut until the end of October to finish paying some things off and saving as well. I will be bringing $3000 with me in May. So, I’ve been searching on Craigslist for some room shares in the $400-$500 range. I found a couple of “work trade” postings, is that usual? An elderly couple looking for some help in return for a room or a person looking for some admin and housework in return for a room.

I’d want to stay in an area close to the hotels like Lahaina, Ka’anapali or Wailea. My plan is to find a room to share for the time being, get settled in, really get to know the area, the way of life, and find a job or two ; ) Then, find a good apartment either a one or two bedroom where they accept dogs – which by the way i had no idea it was that hard to find! Then Jason and Kona would come over. I will have a weekly income of $480 coming in on top of the $3000 that I’ve saved up regardless, so although this plan is a little unconventional (temporarily moving away from your spouse) I think it’s the smartest thing to do at the moment. For the both of us to come at once with a dog, with a car, with no jobs, not knowing the area, no friends, no family, would be counterproductive in my mind. We would spend so much money just staying afloat which will then lead to us questioning if this was even a good idea.

Thoughts?? Suggestions??

Thanks again Vern!

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Aloha Jen,

Wow, sounds good. Maui No Ka Oi is RIGHT. I think there is no better island. The work for a place to stay option is something that is quite common in Hawaii, even more so on the Big Island. On Oahu and Maui the stay for providing personal care to someone is common and there are some nice arrangements that can be made. If you will have $1,900 coming in per month and the $3,000 savings to bring, I think you should be alright. Rooms to share for $400, 500 might be a bit of a problem. Hope you can find one at that amount in Kihei or Lahaina. In Ka’anapali you likely won’t. It’s a high-end tourist area with expensive hotels mostly.

I think you’re right in splitting up for a bit and going to check out the situation on your own. I frequently suggest that, just did it in another post before this one. I think it’s the smart thing to do – and can help solidify your plans considerably. Smart move!

Best of luck to you and your family. Do write and let me know how it’s going for you when you get to Maui to scope it out!


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. Olivia 03/20/2018 at 3:50 am - Reply

    Hi, I am looking for suggestion, advise, thought…anything can help :)
    I am making plan for 2-3 years to move. I visited Kona, Oahu and Maui and I think Maui is where I hope to be but Job and Health Insurance is the huge concern for me. I live in the Midwest, single and I don’t have any mortgage debts. I work as an administrative position for a health care provider. Not super high paid range (40-45k) but their benefit is so significant. I know it will almost possible for me to find such opportunity in Maui. I do have a short background working in hospitality industry so I hope these will be my first step once I move there.
    However, I was thinking of buying a condo ahead of time and rent out, probably a year ahead of my final move. Maybe this would help me somewhat settled when I get there and also allow me time.

    I am not sure if this will work and still unsure about how it works with buying a property there while i am still here…and the world of property management in Maui…

    • Peter Kay 03/20/2018 at 8:57 am - Reply

      If you could afford a condo in Maui (have you look at the prices?) you could make it work though I would not recommend making such a huge commitment without living there for several years. Many people go to Maui only to realize it’s not for them. Renting it out is not a problem. It’s the cost of owning it that’s your hurdle.

      • Olivia 03/22/2018 at 4:08 am - Reply

        The ones I looked at were around 300-350K?…Even if after few years I found out Maui is not so much for me, I could sell and move? maybe to another island?
        But I am determine for Hawaii…just need to make proper plan.

        • Peter Kay 03/22/2018 at 7:10 am

          Have you ever been to Maui before where those $350k condos are? Your plan might work but I’d strongly recommend you rent for 6 months before making such a big decision.

  2. Michael & Lorelei Torino 08/11/2013 at 11:45 am - Reply

    I wish you the best of luck. I Michael coming from New Jersey knows how it is to move quite a distance. It was my best decision ever to move to Maui. Not only did I marry the women of my dreams but also partnered up and have a successful business with her. Thank you God!!!

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