Here is an email I got pretty recently about a husband and wife looking to move to one of the islands, but kind of going back and forth about choosing either Maui or Oahu. I think this is a common problem, and one I’ve also beat myself up over for a while too. There are three islands that I think I could live happily on. Maui, Big Island, and Oahu. Having lived on Oahu already for 5 years, I know it well and I know how to find peace of mind there among the large population, traffic, etc. I have some favorite spots that are not overrun by tourists or locals and I can always manage to have a good time. Maui is just about perfect for me, it is very laid-back and comfortable. It’s a good match for my mindset. There is just enough to do – as in shopping, movies, etc. And there are some great hikes and other outdoors things to keep me occupied. There aren’t many people on the island (though growing all the time), and I find people are easy to get along with.

Big Island is also really laid back, and there is only one problem with it – the volcanic fog – VOG. I have a bit of asthma, and I am not sure how I’d get along there longterm. Maybe best to avoid that one.

Anyway, getting on to “Jen’s” situation…

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Hey Vern!

My name is Jen and I have been reading your blog for some time now and it has been such a great resource. A little bit about me. I’m 28 years old born and raised in Connecticut I visited Hawaii back in 2002 with my family and shortly after coming back from an unforgettable vacation I realised (just like many) that I left a part of me there. Fast forward ten years, last april my husband and I spent our 2 week honeymoon on Maui and decided that we wanted to live there.

I have a radio and tv broadcast background and my husband is in construction. My father and sister are chefs for the hyatt hotel corporation so I basically grew up in a hotel. I’ve had every job imaginable. From lifeguarding to bartending to nannying to retail to operating tv cameras to admin work to event and marketing coordination. Jason, my husband, on the other hand has had the same job for the past ten years…he is definitely the ying to my yang! We also have a dog his name is KONA and we are definitely bringing him with us.

But to which island? My heart is leaning towards Maui but my mind is saying Oahu. Jason and I like being outdoors, going on hikes with our dog, swimming etc. We’re homebodies for sure but do like being social and go to the neighborhood bar from time to time. The reason why my heart is saying maui is because we need to slow down. The northeast in general does not have a great work/life balance. its go go go all the time! however we DO need jobs so thats why my brain says Oahu. I keep going back and forth. Help!

Thanks again!!!

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Hi Jen,

Maui is an incredible place. I interviewed for a job there, the first time I visited the island, and I walked around with my head in the clouds. Maui is as perfect as island living gets – in my opinion. I got the job and moved over for a year, and absolutely loved it. Maui has a style that doesn’t fit everyone.

Maui is:

1. Beyond beautiful. It has some amazing places – Hana, West Maui Mountains, the sea-cliffs on the west side, amazing state parks with beaches. Great views of Lanai and Molokai, Kahoolawe. It is hard to say Maui is more beautiful than any of the other islands, it is just my personal bias I think.

2. Expensive. If you have money, you will enjoy Maui more. That’s again, my bias. I met more people on Maui making over $100,000 per year than the other islands. Maui can be very nice if you are making enough money. Otherwise, it can be a bit of a struggle, but, no less beautiful!

3. Not very crowded. Though I could do with less people on the island, it really isn’t too bad. Traffic is not horrible. Public events are not usually so packed you cannot find parking somewhere. People are not stressed out because there are too many people on-island. It’s a good atmosphere, not too many people on Maui.


Looking at south central Maui from Kula, at the base of Haleakala Volcano. A very laid-back place, don't you think?

Looking at south central Maui from Kula, at the base of Haleakala Volcano. A very laid-back place, don’t you think?
Scenes from the Kula Lavender Farm – Due West by John Morgan is licensed under CC BY 2.0. Image may have been resized or cropped from original

That sums up the three key points of Maui in my mind. It has a lot, one thing it doesn’t have – is jobs. Since you are going back and forth on which to choose, Maui or Oahu, I think the best idea is to just move to Oahu first. Get used to island life. Get used to the way people live in Hawaii. It is quite different and will take some getting used to. Once you get established on Oahu, then consider moving to Maui. Go visit Maui first, see the island, research jobs there. Jen, you should have no big problem to find a job on Maui since you have so much hotel experience. Go check it out and see what the market looks like for what you want to do.

Oahu can be slow, it depends on you. As I said at the beginning, I can live on Oahu and be pretty content. It is not my first choice, but, jobs are much more plentiful and Oahu has everything the other islands have… there are just more people to enjoy them.

I think the best advice I can offer is to plan on moving to Oahu and then make it a goal from there to move to Maui later if that’s what you both decide will work. You might even have a look at Big Island, it is similar to Maui, but less expensive.

Ok, best of luck to you both!


Peter Kay