Living in Hawaii – Which Island is Right for You?

Navigation:/, Moving to/Living in Hawaii – Which Island is Right for You?

Living in Hawaii – Which Island?

The islands are quite diverse.  If you like nightlife – you can only live on Oahu. If you like quiet, intimate gatherings on the weekend – you could live on any island, conceivably.

You’ll need to visit all the islands if you want a big choice, otherwise try Oahu, Maui, and Big Island. Few can live on Kauai, Molokai, or Lanai – they have small populations and, though beautiful, are not usually something most people can handle. The solitude becomes too much!

Living on Maui

Over 152,062 lived on Maui as of 2017. When I lived on Maui I felt like there were far less than this because the majority live in the central and southern Maui region. I was on the west side of the island and there aren’t very many residents or tourists there in comparison.


Jobs are predominantly in the tourism area, and, as on all islands – some in  construction. Healthcare is picking up as elderly Californian’s that bought homes in Maui, move to the islands to retire and need nursing and other periodic care.

The best places to live for nightlife and other activities?

Kahului (central), Wailea (south), and Lahaina (west).

There are daily flights to Oahu and the other islands, sometimes they are even cheap. In the past there have been airfare wars in which fares dropped to $25 to $50 per flight! Don’t count on this – the typical fares are in the $200 for interisland flights.

In my own opinion – Maui is the ultimate island to live on if you have the money to fly to Oahu often for shopping, nightlife, or other things you crave that you won’t get on Maui. Maui is filled with good people, and the most beautiful scenery. There is less to do on Maui than Oahu – but, that’s OK because the lack of crowds at the most beautiful spots make it all worth it.

Living on Big Island, Hawaii

By far the biggest island, and able to hold all the other islands within its boundaries if placed on top. The Big Island has active volcanoes, world class big game fishing, and a whole lot of land to explore if that’s what gets you excited.

The island is enormous in comparison to any of the other islands – over 4,000 square miles. The road around the perimeter (highways 19 and 11) take you just 222 miles, but is quite incomplete and not a complete perimeter tour.

You’ll pass through a lot of different topography on a round the island trip. The Big Island is diverse and impossible to see in a month’s time – all there is to see.


Tourism, some construction, and agriculture are what you’ll find here.

The population as of 2015 is just 196,000+ and people are spread out quite a bit. There are two main towns – Hilo (east) and Kona (west), and each is very different from the other.

Kona Side

Kona is very dry and rugged terrain. It is the focus for tourists to the Big Island of Hawaii for a few reasons. One being that the rain is not so abundant as it is in Hilo. Kona gets around 25 inches of rain per year on average.

Kona’s beaches and bays are ultra beautiful and are relatively easy to access.

Some major resorts have opened in Kona over the last 25 years – resulting in billions of new dollars coming in construction alone.

This side of the island gets a lot of sunshine – I mean a LOT. Kona has the most sunny days of anywhere in Hawaii. As a result the place is built up much more than Hilo – and there are so many things to do in Kona you’d not run out anytime soon.

Facing the leeward (windless) side results in Kona’s mild waters. Swimming, bodyboarding, snorkeling, surfing, body-surfing – any water sport can be enjoyed daily. The water is said to be the most clear in the state at Kona beaches.

The beaches are perfect – some of them making it into the yearly top 10 of America’s beaches often. Hapuna is one such beach!

Hilo Side

Hilo is the world’s wet weather capital with over 125 inches of rain per year on average. Yes, that is over 10 inches per month! Most of the rain falls at night (thankfully), but during the day – brief and intense showers can pop up at any time.

Could you live with that? Many cannot and choose Kona instead.

However, because of the rain, Hilo is the greenest part of the island. Flowers, fruit, and vegetation abound. It’s like the green side of Kauai – truly beautiful flora. The waterfalls are amazing on this side of the island – and there are no waterfalls at all in Kona.

The beaches in Hilo are also beautiful, but not so easy to access. There are a some black sand beaches that should not be missed on a trip here. If you’re coming for the beaches, you could visit Maui and see black and pink sand beaches too though.

Hilo is akin to old-Hawaii. It is ultra-laid back, and in contrast with the up and coming Kona side of the island. Hilo is for those that love nature, quiet, and that can deal with the near constant rain. Native Hawaiians choose to live in Hilo more than Kona. It’s a rather private and simple place that looks a lot like the Hawaii of long ago.

Some say that visitors in Hilo are just tolerated – and not really welcome. Of course businesses wouldn’t’ say that, but those that have lived here for years see any advancement of the area toward increasing tourism – as a step backward.

Most people moving to the Big Island live in Kona and visit Hilo when they can for the waterfalls and different beaches.

Living on Kauai

Kauai’s population is just north of 67,000 in 2017 and has tourism as its main support.

Kauai is a lush, green, flower-covered island with many birds, turtles, and fish varieties.

If you chose to live on Kauai you should probably make friends quickly because people are quite spread out across the island. I have a friend living there now that moved to Kauai on a whim, and now is sort of regretting it. He thought it would be easier to find a job than it has been, and he doesn’t have any good friends (going on 5 months), only acquaintances.

Kauai is probably what you picture Hawaii as being like if you’ve never visited the islands. When you disembark from your plane and walk across the tarmac, marveling at the tiny airport – you’ll imagine – immediately – living there for the rest of your life. Everyone does! Few can make it work.

I don’t imagine many of you reading this book will ultimately choose to make Kauai your home. Honestly, in my opinion, I wouldn’t recommend that you do – because I just think it’s not a match for what most people want long-term.

Feel free to prove me wrong and send me email with how you’re getting along so well there! I’d love to hear it!

Living on Molokai and Lanai

These two islands are beautiful, and almost barren. There are few people on either. Moloka’i boasts 7,000+ inhabitants, and Lanai has less than half that number. Moloka’i has Hawaii’s highest unemployment rate – usually.

You might decide to live on Moloka’i or Lanai if you are a writer, or need solitude daily to keep you happy. There is plenty of it!

Moloka’i is located between Maui and Oahu.

Moloka’i is 38 miles long and 10 miles wide and has a land area of 260 square miles. Moloka’i is well known at the place where Father Damien de Veuster, a priest originally from Belgium, lived and cared for those with leprosy.

Today there is no contagious leprosy. There are still some patients with the disease living on the island and being treated.

More info available at, Molokai’s official site.

Lanai is a smaller island than Molokai ‘I and is basically a large pineapple plantation. There is one town – Lanai city with about 3,200 people living there. The island is controlled by Maui County.

If you’re planning to visit the island you will need to rent a 4-wheel drive vehicle because most of the sites are located down long and bumpy dirt roads.

Living on the Most Developed Island – Oahu

The island of O’ahu is only about 65 miles at its longest stretch, and 111 miles around the perimeter. Oahu has the most people by far (953,000+ as of 2017) of all the Hawaiian islands, and even more than the rest put together. Most people choose to move to Oahu for the variety of things to do, as well as the ease of finding part-time or full-time work. Oahu’s beaches are every bit as lovely as most of those on Kauai and Maui – and you’ll have access to world class shopping and entertainment on Oahu.

On Oahu is Honolulu – the capital of Hawaii, as well as Diamond Head Volcano, Pearl Harbor, the “North Shore”, and Waikiki – all of which I’m sure you’ve heard of already.

Oahu has more jobs, more roads and highways, more shopping, more tourists, more things to do, than any of the other islands. With all that comes a price. I’ve heard someone refer to Waikiki as New York City on a beach. That’s close, but Waikiki still has its charm.

There are many hotel high-rise buildings in Waikiki and in Honolulu in general. Waikiki is space-limited and so construction goes up vertically, not laterally across more land.

Job areas on Oahu are more plentiful in these areas:

  • Tourism
  • Government and Military
  • Construction
  • Agriculture
  • Healthcare
  • Retail

Living in Waikiki

Waikiki is the center of Oahu, the place where most tourists choose a hotel, and many activities are centered here. The prices are high for nearly everything, as you might expect.

If you are fond of nightlife – you’ll love Waikiki as the major clubs are all located here. Restaurants of every variety are here, like in every big city – but, with an emphasis on Hawaiian and Asian foods. You can probably find a German restaurant if you look for it, but I don’t remember there being more than 1-2 Indian restaurants. If you like Korean, Chinese, Japanese, Vietnamese, Italian, fusion style restaurants, or sandwich places – you’ll feel right at home in Waikiki.

Shopping for food in Waikiki – or anywhere in Hawaii, is probably going to be eye-opener number 2 after the high rental costs.

If it seems like everything the checkout person runs through the register costs more than $5, that’s because it DOES! I first noticed this back in 2002. I was astounded, that after shopping for 90 minutes I didn’t have one thing in my full cart that was less than $5. You might find that too, don’t be surprised. It’s nearly impossible to go grocery shopping and come out spending less than $50 and probably more like $200.

There are few grocery stores in Waikiki – the one that I always used was near Ala Moana Shopping Center and behind 747 Amana Street. It was always crowded, and there is a limited selection of foods. The other alternative is to shop at the local ABC Stores, but they are very high priced – and again, with a limited selection.

There are Costco’s, Sam’s Club, and other grocery stores around the island and it pays to shop at them for certain things you need. The entire population of Hawaii is cost-conscious when it comes to food shopping – so find out from friends where they shop for the best deals.

Living Elsewhere on Oahu

There are many sections of Oahu in which you can live. Waikiki is great for those that like action and things to do – everything is within walking distance, bus distance, or bicycle distance. Many people ride bikes to get around so they don’t need to worry about paying for parking and sitting in traffic.

Living in “Town”

Waikiki, Manoa, Punchbowl, Makiki, Kaimuki, Pali, Diamond Head, China town, are all considered the town area. Town is crowded, but packed with things to do. There are many, MANY high-rise buildings packed into this small space – almost all of them are places to house residents and visitors.

Town is the most expensive area, and the one that locals usually prefer to avoid living in because it is nothing like the “real Hawaii” they know and love.

Life on the Windward Side

Kaneohe, Waimanalo, Kailua. In my own opinion this is the nicest area on Oahu, next to the North Shore. There is lush foliage, thanks to the rain that comes almost daily in this area. The water is crystal clear, and there usually isn’t that much traffic (Kaneohe being the exception at times). Still, nothing like Waikiki or Pearl Harbor traffic.

Kailua Beach Park is nice, and a locals favorite has now been exposed to the world with a recent ranking of “Best Beach in America”.

Kailua has some outrageously priced real estate for sale. One of my former co-workers owns almost a dozen homes here – and he isn’t selling.

In the last couple of years more and more business has come to Kailua and it is now a quaint shopping district, topped off with the amazing Kailua Beach.

Kaneohe has also grown considerably, and has a new mall. Some of the homes are astounding, and on the whole – Kaneohe has never looked better. The Ku’uloa mountain range and cobalt blue ocean views are spectacular. The waves are small and there is little coral in the area – making it ideal for bringing the family.

Waterskiing, fishing, kayaking, kite-surfing (surfing with a kite to lift and power you around) are all activities you can enjoy not just in Kaneohe, but all over the northeast of Oahu.

Laie, Ka’aawa, Hauula are all very small areas on the way toward the north shore from Kaneohe. They are very quiet and if seclusion is your ideal – you can live here and love it. Homes are expensive, and there is very little in the way of apartment or room rentals. If you live here and need to commute into town you can count on about an hour average each way.

Living in East Oahu

Hawaii Kai, Kahala, Aina Haina, Diamond Head areas.

If you are at Waikiki’s “The Wall” and driving toward Diamond head you’ll enter into another world where there are less condos and the focus is more on residential living. The homes have a little more land, and it’s probably a lot like where you live now – assuming you have palm trees, flowers, fruit trees, and a view of an extinct volcano in your neighborhood.

Once you get through the residential section you’ll hit the H-1 freeway and there are some businesses along there, under the H-1, including Kahala Mall, Starbucks, and some great pizza places.

Hawaii Kai is the area with a view of Koko Head Volcano, right before the road climbs the lava cliffs leading to Hanauma Bay, Sandy Beach, Makapu’u, and other great beaches. Hawaii Kai is a large, well-planned residential area with canals on deep water for those of you with boats you want to be able to take out on the Pacific Ocean.

There is quite a procession of cars moving from Hawaii Kai to two in the morning and at rush hour in late afternoon. If you live here you can count on 40-60 minutes commute in stop and go traffic daily during the week.

Many people that move from the mainland USA to Oahu choose to live in Hawaii Kai, as it resembles the type of residential neighborhood they are familiar with. It looks mainland-ish in a way, and yet the beauty of it will knock you over. It really is a great place to live, I have a couple of friends that live there now – and I don’t get tired of visiting them!

Average prices of homes in Hawaii Kai – is the highest in Hawaii at around the $1 million range.

West of Pearl Harbor

Ewa (eva), Kapolei, Makakilo.

Eva is a very local area, but there are quite a few transplants that end up buying homes there. A local guy I worked with in the Air Force years back was from Ewa and he used to talk about it like it was the ultimate place for Hawaiians to be from.

Target (store) came to Ewa, there are numerous little shopping centers and a brand new mall is being built at the moment. The west side is untouristy – you might see no tourists except at the gas stations and big water park in Kapolei.

Kapolei and Makakilo are residential apartment neighborhoods that are rather affordable and within an hour’s commute of town. There are many new buildings in Kapolei, and my girlfriend had a 2 bedroom apartment with dining room, family area and large back porch for $220,000 back in 2004. In 2016 the median home value is $556k.  As many real estate agents always say, the best time to buy is right now!

Leeward Side (windless side)

Makaha, Nanakuli, Waianae.

The beaches and coast of the west side of Oahu are beautiful, though it is nowhere near as lush and green as the windward side. The homes in this area are truly “locals only”, and I have had a couple of bad experiences driving through this area. Once when I had taken a wrong turn, in an area I wanted to explore. There were 4 locals with knives showing them to me as I drove in.

Needless to say I reversed and drove right back out.

Housing in this area is dirt cheeeeeeeap. The locals say “cheeeeeep” in a funny way  – you’ll notice it someday.

I think it’s safe to say that nobody reading this book is going to choose to live in the Waianae area, and possibly even Nanakuli or Makaha.

Makaha does have a nice golf course with some newer custom homes that you might like.

Central Oahu (Mililani, Wahiawa)

As you drive up into the mountain over the H2 freeway toward the North Shore from town, you will see Wahiawa and Mililani. Mililani is a nicely planned city that has a great residential atmosphere to it. Plenty of people live in this area – there are many new and old homes to choose from if you choose to live here.

Housing costs are cheaper than town and there are some good schools in Mililani if you have children. Mililani has a military base and there is a large population of military living around the base. Mililani and Wahiawa can be cooler because they are up in the mountain a bit. There are breezy sections and also areas where the wind is blocked by the many trees.

You should have a look at this area if you’re considering moving to Oahu, many find the atmosphere more in line with what they are looking for.

Pearl City, Pearl Ridge, Aiea, Halawa

Pearl City is like town outside of town. It’s located near Pearl Harbor, to the west of Waikiki and the airport. It has a rather large resident population and there are many condominiums and houses to choose from if you want to live here. The area is rather dry, and the roads are in good condition.

Homes are a little older – 1960-1970’s usually, though some are beginning to tear down the older homes and replace them with newer construction these days. Houses usually have a small yard in this area.

The commute from here to town is about an hour each way during weekdays.

If you like you can get a home up on the hill – and have a view of Pearl Harbor, or even to Diamond Head Volcano.

Aloha Sports Stadium is here, as is Pearlridge Mall – a giant shopping center with all sorts of businesses. If you need it – you can find it at Pearlridge. Surrounding the mall are many other stores – so you can find what you’re looking for – whatever it is.

There are a couple of hiking trails that I’ve explored in this area. One I remember in particular is a short one – the Aiea Loop. Oh, and the Aiea Ridge Trail too. I remember finding wild strawberry guava to eat, as well as mountain apples (rose apples).

North Shore (Haleiwa, Sunset Beach, Pupukea, Waimea)

As you crest the mountain top and look down on Haleiwa and the coast of the North Shore you will be “glad you stay Hawaii”. The view is magnificent and if you catch it on a clear day you can see the different blue hues of the Pacific Ocean. Locals call this area “country” and “up country”. The North Shore is magical when it comes to surfing. The Pipeline is a place where the wave curls into a perfect tube – one of the few places on earth where big waves turn into tubes.

It’s fun to watch a professional surfing event at the North Shore – the power of the waves, the grace of the surfers, is humbling and a great experience.

Homes on the North Shore are expensive, and either small or gigantic. Most homes are older and small, and packed with people living in them because the location is so idyllic. Many pro surfers from around the world are welcomed into homes of residents living on the North Shore – sometimes staying for free!

The coast is rugged, and the waves – world class, during the winter and flat during most of the summer.

If you hear about 30+ foot waves on the north shore, you should jump in your car and immediately head up to either the North Shore Beach, or Waimea Beach to see how big they can get. I’ve been there during 50 foot waves at Waimea and it’s quite a site. The only other place that regularly gets bigger waves than Waimea Bay is “Jaws” in Paia on Maui.

Living on the North Shore is probably not for you if you’ll be in town often. With no traffic you can reach town in 40 minutes. With traffic – over an hour. There is little on the North shore except a small grocery, some coffee and pizza shops, and the clothes shops in Haleiwa for t-shirts, surfboards, and world famous Matsumoto’s Hawaiian Shave Ice shop.


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. Sade 01/06/2019 at 1:42 am - Reply

    Peter, For a family with 6 kids where both mom and dad work online business, what islands would you recommend? (We have a large stable income, and will never need to work outside of the home) We are not much into shopping at malls or night life, would like to live a laid back slower life, but still would like access to the occasional movie and restaurant. We also want to grow our on fruit trees.

    • Peter Kay 01/06/2019 at 7:16 am - Reply

      This video should answer that question: Which Hawaiian Island is Best for you?

      • Jennifer 01/12/2019 at 5:08 am - Reply

        Hi I am possibly relocating to Maui and was wondering about the wind. I heard it’s very windy but not sure what parts are less windy and how often throughout the year. Is Kona side and Lahaina side windy? I am also a bodyboarders. Wondering if the Kona side has any good beaches for that.

  2. Ryan 12/03/2018 at 1:12 pm - Reply

    Why is Costa Rica one of the lowest on your list of alternatives? Thanks!

  3. Dennis Watson 11/26/2018 at 1:36 pm - Reply

    My husband and I would love to Move to the big Island, with our 9 yr old daughter. There seems to be a lot of affordable home in the south west part of Hawaii, Puna, etc..Is there a big drawback that I am missing? Besides the volcano areas”?

    • Peter Kay 11/26/2018 at 2:12 pm - Reply

      The most accurate, objective thing I can say is that the laws of economics are in full effect in Hawaii. So if there is a low price it’s either due to high supply or low demand. The SW part of the Big Island has had no significant events which would have created an oversupply. Hence we have low demand. So your “Is there a big drawback?” answer is: yes, there must be big drawbacks which account for the low demand.

      It’s like asking why in a crowded shopping mall at peak dinner time where all the restaurants are packed, why is there one that’s almost empty with super low prices? What might you be missing?

      • Peter 12/27/2018 at 7:57 am - Reply

        Peter I am thinking of snow birding on Moloka’i. I spent 25 years doing so on the Big Island and loved it until this last volcanic eruption and before that the gas vent. I have asthma and have given up on the big island the vog is too hard on me. I am actually thinking After the Big Island Moloka’i would be the cheapest place for me to purchase a condo. I understand it can be lonely on Moloka’i and I am concerned about that but I love the outdoors and don’t enjoy the tourist attractions so I am thinking it might be a good fit. My plan would be to spend three months a year on island, swimming, snorkeling, spear fishing, kayaking, fishing, surfing, hiking, four wheeling and hunting. Other than wishing me luck any words to the wise?

        • Peter Kay 12/27/2018 at 9:13 am

          Not sure what you mean by “snow birding” but if you mean “snowboarding”, there’s no such thing on Molokai. From your comment I’d say you’re looking at numbers and not the actual reality of the place. I would say you should definitely go to those places for a vacation first and see if it feels right.

  4. Stephanie L 09/13/2018 at 10:23 am - Reply

    Peter, will you please give more detail as to why it is hard to live in Kauai? You say that few have been able to and you wouldn’t recommend it. It’s the island I thought my husband and I might consider retiring to. We’ve travelled there every year for the past 5 or 6 years and just love it. So, please give your honest insight.

    • Peter Kay 09/13/2018 at 10:33 am - Reply

      I love Kauai. It’s my favorite island other than Oahu. My “hard to live” comment was related to the economic situation and I stated why. I said it’s the best place for hiking. What details are missing?

  5. meaghan richmond 09/13/2018 at 8:32 am - Reply

    Hi!! I am in a spot to purchase another home and am looking to make a move to the beach. Currently I live in Breckenridge, CO and have converted my home to a very successful Adult hostel on air bnb. Catering to single and couple travelers that want privacy but connection. I am a medicine woman and offer energy work and coordinate trips to Peru and Brazil; additionally I offer plant medicines myself, as a shamanic practitioner. I am hoping to grow both realms of my business some where warmer and am torn on the Caribbean or Hawaii. I am 32 and single, looking for a spiritual community that still thrives on tourism but is not overwhelmed with it. Most importantly, i want to swim in the ocean and run on the beach every day (so looking for sandy not rocky beaches). I dont need to walk out my door to the beach but hoping it would be a bike ride away. $600k is my max to buy a home and I would be living on about $100k/year. Thank you so kindly for any advice <3

    • Peter Kay 09/13/2018 at 9:05 am - Reply

      You can’t get anywhere near the beach for less than $1.5M (2018). $600k buys you a “cheap” 2 bedroom condo.

  6. Jackson McIntire 08/30/2018 at 2:04 pm - Reply


    23 year old here looking to move to Hawaii from Los Angeles in the next year. I’m a bit cautious of Honolulu as I’ve heard crime rate is high. I am looking to possibly share a 2 bedroom apartment with someone. The type of area I am looking for would be one that has beautiful scenery and not TOO many people, but not too few people either. I don’t need huge clubs, but a few bars with young people would be nice.

    Do you have any recommendations?


    • Peter Kay 08/30/2018 at 6:17 pm - Reply

      The crime rate is skewed due to lots of petty thefts related to tourism. Otherwise it’s a very safe place. Your requirements are pretty basic and relatively speaking has a lot of options so assuming you can afford it, you should be able to find something.

  7. Denise B 02/01/2018 at 2:54 pm - Reply

    Hello Peter,
    I (like many) just read this post and enjoyed every line of it, I am planning a move with my (future tense) two teenage sons by 2020, I work in Welfare right now and want to continue that line of work when I get to the islands. I am wondering where would be a good place to look into for me and my sons, nightlife isn’t that important to me but it could be nice for an escape considering I am living in Las Vegas now, but I want to be somewhere that would be close to my job and affordable. Do you have any more insight for me? Thank you!

    • Peter Kay 02/02/2018 at 9:48 am - Reply

      Thanks Denise! I think Oahu is still the best all-around island as you get essentially get away if you really want to yet you have all the modern conveniences of a good-sized city nearby.

  8. David 01/24/2018 at 4:35 pm - Reply

    Hey Mark! Been reading a lot of your posts, very informative! We’re headed to Oahu Feb 4 to begin our quest for a new life. Originally we were thinking Oahu, but now are torn between Oahu and Maui. Will probably spend time in both during our 2 week stay. The plan is to make the actual move end of March this year. Thank you again for your helpful posts!

  9. TIANNA 01/14/2018 at 11:17 am - Reply

    I read everything you wrote and it was very helpful thank you! I just came back from Hawaii and felt a big draw to move there, mostly for the magic and healing aspect of the islands. I’m a 28 year old acupuncturist and have a possible dream job opportunity in Hilo, which I visited for only a few hours, but am a bit concerned about the culture fitting my lifestyle. Currently, I live between Venice, CA and Boulder, CO- two very active, upbeat, artistic, and “young” places. In both Venice and Boulder I have a beautiful community of conscious and like-minded people which i value very much. I’m the type of person who absolutely loves nature and quiet, yet can feel lonely and isolated without some action and a strong community. When I visited Oahu, that felt more like my vibe though possibly even too active. Do you think Hilo has a young, active community that I could merge into? My other concern with Hilo, which you wrote about, was the fact that the beaches are rocky and not that easy to access. Could you elaborate on that a bit? Thank you so much for your time and perspective!

    • Peter Kay 01/14/2018 at 11:43 am - Reply

      My recommendation is I would spend about a month in Hilo before making any kind of final decision so you could see if it is right for you. Hilo is not known as a place for the young crowd. Oahu, however, as you discovered, is generally speaking more of a hipster type place.

  10. MarkG 10/08/2017 at 1:30 pm - Reply

    I love Hawaii but not as a place to live. The reason is simple. Every since the U.S. stole Hawaii from the Queen and made it a state, greedy developers have snatched up huge chunks of land. As a result, most of the natives cannot afford to live here. Now, consider this. Look up what the prices for property were in Hawaii back in 1970 and you may have a heart attack. So what do I recommend as an alternative?

    Easy, but you may need to learn another language. You have all of South America to choose from. Some countries are better than others. Belize is wonderful and one of the few countries where english is the native language. I love Chile, Argentina, Panama, and even Costa Rica, although I would keep that one far down on your list. Mexico is also nice but try to stay close to the U.S. border. And remember, there are some states in Mexico, as well as some countries in South America, that will not allow foreigners to own property on the beach. This is, again, thanks to greedy developers who have comes to these countries and snatched up large chunks of land.

    Anyway, now that I’ve gotten this off my chest, let me continue my initial though. Hawaii is lovely and it is magical. If you’re ok with spending $900k for a matchbox of a home on any of the smaller islands, then go for it. However, if you want a small chunk of property, like me, and want to build a natural home made out of hemp and/or bamboo, then you must go beyond the borders of Hawaii and buy a small piece of property that you can benefit from. And, as far as I’m concerned, if you go the unconventional route and you move to SA you have truly aimed for awesomeness. Just don’t build your home and stay inside looking at the four walls. Life is too short. And we are all merely the players. So go play. Be it Hawaii, Mexico, or SA.

  11. Cheri 08/16/2017 at 11:01 am - Reply

    I’m considering relocating to possibly Oahu to teach . Any suggestions comments etc. I’ve never been to Hawaii . But I love tropical climates and the beach

    • Peter Kay 08/16/2017 at 12:11 pm - Reply

      Terrific! Best suggestion is to read every page on this website and then buy the book! :)

  12. Sandy 07/31/2017 at 9:24 am - Reply

    I’m retiring July 2018 and would like to move to Hawaii, not sure of exact location. I am wondering about the Craig’s List posts that offer “free tenting” in exchange for 14/15 hours of work each each on the grounds or cleaning. Do you know anything about these farms?

    • Peter Kay 07/31/2017 at 9:28 am - Reply

      I don’t have any first-hand (or 2nd hand for that matter) knowledge of these “Free tenting” but I would venture to say that if you’re at retirement age that’s not going to be a good match for you. My sense is that this is for young “kids” that want a low-cost camping-deluxe adventure. This is really just my guess, though. I don’t have data to back it.

  13. Jean Johnson 07/20/2017 at 10:25 pm - Reply

    Is there a place to live off the land in Hawaii? I work in Hospice and really just need a break for a while. I want to live in Hawaii and just breath. I don’t care about the night life or shopping malls and love being alone.

    • Peter Kay 07/21/2017 at 8:07 am - Reply

      Can’t help with “living off the land” but regardless, what are you waiting for? Come for a vacation at the very least.

      • Jean Johnson 07/22/2017 at 1:04 am - Reply

        Taking the vaca next year. Hate tourists season, so will have to figure out when the best time to go. Thanks for the info.

  14. Kortnee With-a-k 03/25/2017 at 8:46 am - Reply

    What’s the best way to go about finding a place to rent to live (Oahu) in for a few years? Craigslist? A realtor? Other?

    • Peter Kay 03/25/2017 at 9:12 am - Reply

      Craigslist pretty good but regardless you need to know about the place. Take a vacation here first and spend time to get to know the neighborhoods.

      • Kortnee With-a-k 03/25/2017 at 9:44 pm - Reply

        Good advice thanks!!

  15. Ally 02/19/2017 at 6:33 pm - Reply

    This was so helpful. I am leaning towards looking into moving to Hilo. I am not moving to Hawaii for the beaches but for a life. I am planning my first trip this fall.

  16. Leda 02/09/2017 at 5:01 pm - Reply

    From your experience, do you think $60,000 a year is enough to afford rent and life in general in either Maui or Honolulu?

    • Peter Kay 02/09/2017 at 6:26 pm - Reply

      It’s probably “enough” if you can stomach living on the edge of affordability. Rent+car+food+healthcare alone will get you really close to that figure, leaving little room for anything else or any major events.

  17. James Fraser 12/22/2015 at 11:29 am - Reply

    I am 61, retired, income ~30k. I have lived in Kailua Kona for the last 5 years, with no intention of ever leaving. But recently met a friend in Maui, and we are trying to figure out where we should live…for the life of me I can’tell find any comparisons of COL. Suggestions?

    • Vern Lovic 12/22/2015 at 3:48 pm - Reply

      Hi James, Nice to hear you’re on Big Island, what an amazing place! I lived on Maui and I think it must be more expensive overall. I think Maui is the nicest place to live, but the most expensive to live in a nice environment. If you haven’t already, you should go see your friend’s home on Maui. See how he/she lives. See who their friends are. Make sure you’re a good match before you or the other person picks up and leaves their stable environment. Having some sort of roots, or familiarity with things is pretty essential for an ideal life in the islands. At least I think so. It felt a lot more like home when I was in a place for a couple years at a time. Anyway, you didn’t write Dear Abby! I think Maui would be more expensive, but of course you can live any way you like – cheaply or extravagantly. On $30K I think you’re best on Big Island. Aloha!

      • Ken 07/21/2017 at 7:42 am - Reply

        This is good to hear about Kona. We just visited there and the family fell in love with it (me included). Have been surfing the internet looking at housing prices to get an idea of how much it would cost. Really didn’t feel it was too expensive with cost of stuff there. Some things were more than stateside, but it seemed to balance itself out. We have been thinking of purchasing a house as a vacation home for now and then future retirement home. Only ever been to The Big Island and some say we should go to all the Islands before we decide. I fell in love as soon as I stepped off the plane. When I retire, should have about 5-6k monthly income with investment account as backup.

  18. nolan tew 05/28/2013 at 10:21 am - Reply

    I lived in laie/hauula from 1969-1972. i had a job in honolulu near the airport so i had to commute every day. housing then was around 250$ monthly for a house shared with a friendly couple who were students at the local college.I never considered myself a tourist but I did enjoy all the local sites, ie, goat island, sacred falls,kavela bay( which later was acquired by dell web corp). even tho i am a haole I considered myself a local/native.I mingled with friends for luaos and participated in snorkle night fishing near laie point and body surfing at the hukilau grounds.. Now i am retired, single, and getting the itch to return and become a permanent fixture.I need to find out what kind of housing i will find when i get back to this area on a fixed income. my insurance is with kaiser permanente here on los angeles area so that ins will transfer. my biggest concern is finding affordable housing in laie/hauula. i probably wont bring my car but will sell it here and buy another on oahu since matsen lines has tripled the shipping fee . your feedback will be most appreciated. thanx.aloha!

Join the conversation! What do you think?