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!

State of Hawaii Population Table

IslandPopulationCensus Date
Big Island200,6292020

Living on Maui

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 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 is a lush, green, flower-covered island with many birds, turtles, and fish varieties  with tourism as its main support.

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 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 (“eh-va”), Kapolei, Makakilo.

Ewa 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 2023 the median home value is about $1M.  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.