I sometimes turn email into an article about Hawaii here because:

  1. It takes time to read and respond to email, when I could be writing an article instead.
  2. Better to share whatever we’re talking about related to Hawaii so more people can see what we’re discussing.

I received a letter from “Mike” in Connecticut. Mike and his fiancé are considering moving to Hawaii within five years, and wanted to know what I thought about the right island to look at – with some considerations about lifestyle given… Here is Mike’s email to me, and my response.


Peter (if you do not mind my being presumptuous and calling you by your first name), my name is ____ ____ and I have been fiddling around with the idea of maybe retiring in Hawaii. As having never lived there before and only visited the main island once for business purposes, I have no clue where to look for housing. If you do not mind offering an opinion on the subject, I would like to give you an idea of what I am looking for and a little of our personalities.

Looking for a newer home that will last without much work until I pass on or longer priced in the 300k area or less. If that is not feasible then, a condo may be the next best bet as I do not like making tons of repairs and like my bills to be very predictable.

My fiancé and I are both in the 50 year old range and will not be doing this for about 5 more years but, might be willing to start looking now and if we find something, grab it earlier than the move.

We have a bit of a slower lifestyle and love reading books and spending time on the computer. She loves the beach or sun bathing and I like a good sports bar with satellite TV for watching our favorite teams play.

We both like to shop and walk around in nice areas.

We are not too much into the night life but, would love to have places nearby for live music, a good glass of wine and some great restaurants.

Of course safety and security is a must.

Do you have any opinion on which Island and what area of that island would be the best place to start our search?

Kindest regards,


Hi Mike,

Thanks for writing – sounds like a lovely plan to live life in Hawaii!

It sounds to me like Maui is what you’re looking for – but you might have difficulty, no, you will have difficulty to find a place for that amount.

Maui would be my first choice if I was in your situation – and I’d be looking hard to find a place to live that is in that price range, and in a safe neighborhood…

Big Island would also be quite nice.

On Big Island, $300K homes are widely available, and you’ll have to figure out where on the island you would like to live. Sounds like one of the bigger cities would suit you and your fiancé. The main problem I would have with Big Island Hawaii is the vog… volcanic fog. It is not constant, but it is something you would deal with on some level – depending where you chose to live.

BigIsland-BigIsland.com covers vog pretty well – they say this:

Health effects: Health effects from vog exposure vary greatly among individuals. People with pre-existing respiratory conditions such as asthma, emphysema and bronchitis are more prone to the adverse effects of the vog. Common symptoms related to Big Island Vog Index include the following:

€¢ Headaches
€¢ Breathing difficulties
€¢ Increased susceptibility to respiratory ailments
€¢ Watery eyes
€¢ Sore throat

Another problem is the great distance between places. At least in relation to Hawaii – there are big distances between things on Big Isle. Everything is spread out – the island is quite big compared to the others.

Best advice – go visit and see whether Big Island is for you – or not. You might like it just as well as you would Maui. If there is something about Big Isle that rubs you the wrong way – try Maui. Oahu has $300K places in Kapolei and other areas outside downtown, so that too – is an option.
Best of luck to you and your fiancé…


Peter Kay

If you are considering moving to Hawaii and you’d like my take on your particular situation – zap me email and I’ll respond as fast as I can – usually just 24 hours, occasionally in 3-4 days if busy.

Keep in mind that living in Hawaii is different for everyone that plans to make it a reality. There is no one island that will suit every type of person. Hawaii is so variable – weather, people, traffic, costs… that you really have to be there to see the different areas and whether it will work for you. Living in Hawaii is so different from living wherever you are on the mainland USA. Go to Hawaii and experience as much as you can on the different islands, and in the many locations on the island that you’d consider moving to. Figure out your top choices and start looking for a place to live. It might take you a year or more to find the right place to live that fits your lifestyle and budget.

But, when it’s all done – it will have been worth it!

Much Aloha,

Peter Kay