Thinking of moving to Hawaii? Our pros and cons...


Waikiki Beach, Oahu, Hawaii 

Mark Twain:  “The loveliest fleet of islands that lies anchored in any ocean.”

My wife and I are recent early retirees at ages 51 and 48.  Since our early retirement last August (2020), we’ve been slow traveling with our traveling companion Toby, a 13 pound Pomeranian dog.  We’ve spent a month or longer in Ocean City (Maryland), Atlantic Beach (North Carolina), the Poconos (Pennsylvania), Claysburg (Pennsylvania), as well as several other attractions on the eastern parts of the United States.

In this post, I’d like to share our experiences of living in Hawaii and the pros and cons.

In the year 2003, my wife and I decided to move to Hawaii.  We had lived through 9/11 while working in Manhattan (New York City).  I worked one train stop away from the Twin Towers and my wife worked in midtown (35th Street).  

9/11 would have a huge impact in our lives. After 9/11, we didn’t like working in the city.  We sure didn’t like working in tall buildings anymore (or visiting tall buildings).  New York City post 9/11 seemed like a different place to us.  It was no longer a place we enjoyed visiting on weekends or living in...

Even though nothing happened since 9/11, we still feel uneasy thinking about working in NYC.  It was certainly a pivotal moment in our lives.  For us, there is pre 9/11 and post 9/11...

In early 2003, I had quit my job at the start up company due to too many demands on the job.  I had signed on to work IT related stuff, but I ended up working on marketing/cold calling towards the end of my tenure.  I didn’t enjoy it after awhile...

Once I quit that job, I immediately set about researching our move to Hawaii. We bought a book entitled, ‘So you want to live in Hawaii’, and we looked at various apartment rentals in Hawaii.  We didn’t want to book a long term rental sight unseen, so we instead booked a hotel for a week.  

We had previously visited Hawaii on our honeymoon back in 1996 and we always had an affinity with Hawaii.  We’re sure we weren’t the only ones...We dreamt about living in Hawaii, with its swaying palm trees, the beautiful sunsets, and the warm, friendly people.

During the next several months, we would put our co-op for sale and start getting rid of our belongings.  We admit we were greedy selling our first home.  We thought we could get more, which delayed our sale.  It took 7 months(!) to close on the co-op.  Lesson learned...Always sell at market value and don’t be too greedy!

So in November 2003, we bought our plane tickets to move to Oahu, Hawaii.  We knew we wanted to live in or around the Waikiki Beach area due to many job opportunities there.  Granted, these job opportunities would be in retail or tourism, but it would’ve been easier compared to a suburb.  

We had donated most of our belongings to Salvation Army in October, so we packed about 5 large suitcases for our move.  It was Thanksgiving Day 2003.

We booked one week hotel in Waikiki, not knowing how long it would take for us to get a permanent rental or when we would get jobs.  I remember waking up the early in the morning, due to jet lag and time difference, the day after Thanksgiving Day, pondering our move.

I was looking out the window of our hotel and I was looking at the rising sun coming up over the Diamond Head Crater to the east.  I remember enjoying that view along with the views of Waikiki hotels and the Ala Wai Canal, which borders northern parts of the island that is Waikiki.

Already by 6 am, the city was bustling with traffic and people.  It was like we never left New York City!

We got up and went out for some breakfast.  We immediately fell in love again with Waikiki.  It was exactly how we remembered it.  We went into an ubiquitous ABC Stores (you’ll see millions of them in Hawaii!) and bought some food and sunblock lotion.

We felt like we were on vacation!

Once we settled in, we went about looking for a long term rental.  Due to the holidays, all the real estate agencies were closed.  Not one place was opened the day after Thanksgiving Day.  We gave up that avenue, and we started walking into condos, condotels (combination hotel & condos), or regular apartment buildings where they had an office, asking about long term rentals.  

We struck out every single time.  We had almost given up when we found a friendly local gentleman washing his Toyota Tacoma truck.  We struck up a conversation and my wife asked him if he knew anyone who was renting out an apartment.  

We were ecstatic when he said his best friend was looking for tenants right there in Waikiki!  We immediately called the landlord and we magically got a rental!  We couldn’t believe our good luck!

We would rent that apartment for the next four months, until we bought our condo right outside of Waikiki.  Until then, we took full advantage of Waikiki Beach area.  We took one month to properly see the island of Oahu and Waikiki Beach.  

We would take our beach chairs everyday to the world famous Waikiki Beach to take in the sun and to swim.  We would go back to the beach for unbelievable sunsets!  We would walk around the main thoroughfare, Kalakaua Avenue, to enjoy shopping and dining out.  We booked tours around the island of Oahu: snorkeling at Hanauma Bay, doing the circle island tour, trip to Pearl Harbor, driving to the North Shore, and eating plenty of seafood!

That first month was simply amazing.  We felt like tourists on a month long holiday.  We thought life couldn’t get any better than that!

Here’s a spoiler.  Visiting Hawaii vs living in Hawaii are two different things.  When you’re on vacation and you don’t have to work for a living, then life is just awesome.  You simply cannot top the natural beauty of Hawaii.  If you love seafood, Hawaii has daily catch of the day, like popular mahi mahi and ono (wahoo).  Hawaiian people are also friendly and incredibly helpful.  We understand the feeling of ‘aloha…’

It’s not faked…

Despite all these, our ‘honeymoon’ with Hawaii was over after about a year.  After that I started to miss my family and friends back in NY.  I also got tired of living in an island.  We needed to get our retirement in order, but our jobs working retail making minimum wage, didn’t help our cause.  

This longing for family/friends were exacerbated by our trip to NYC to visit our family/friends in 2005.  When we went back to Hawaii after a two week visit, I really wanted to go back to spend time with them...

Long story short, we moved back to the east coast in March of 2006.  We chose Pennsylvania as it was close enough to NYC (2 1/2 hour drive), and it had much better job prospects.  Moving to Pennsylvania would prove to be the best decision we made financially, as my last job would allow us to retire early.

Without further ado, please see our list of pros and cons of living in Hawaii!

Pros of living in Hawaii:

  • Natural beauty
Hawaii is still our favorite place we’ve visited in terms of incredible natural beauty.  Nowhere in the world will you find a place that caters to everyone.  You have awesome world class/world famous beaches, mountains, and unimaginable number of plant life and animal life.  For lovers of nature, Hawaii can’t be beat!

Beaches like the Waikiki Beach, Ala Moana, Kailua, and Lanikai are all beautiful and unique, and should not be missed.  There are hiking options:  Diamond Head Crater, Koko Head Crater, Waimea Valley, Makapu’u Lighthouse Trail and more.  

There are rainbows almost everyday in Hawaii!  Just look up towards the mountains from anywhere in Hawaii.  Sunrises and sunsets are unmatched anywhere!
  • Convenience of a city
If you live in Oahu, Hawaii and you live in Honolulu, then you’ll have the services and attractions of any major city in the mainland USA.  There are museums, concerts, theater, aquarium, zoo, government services, public libraries, among others.  

Because flights to Honolulu come and go all day from everywhere, you’ll have no problem getting things you want.   For example, steaks from Japan and Argentina, lobsters from Maine, etc.

Whatever you want, you can probably get it in Oahu, Hawaii.
  • English is the main language 
You don’t have to learn a new language!  This was a godsend for us.  Even though we traveled about 5000 miles from New York City, we were still in the United States.  

If you’ve traveled abroad, then you know what it’s like to not needing to learn a NEW language!  It makes everything so much easier.  From changing your driver’s license to signing an apartment rental lease, everything is easier...When we bought our condo, we were so thankful the language was in English!
  • Aloha spirit
Aloha spirit, of Hawaiian’s belief in welcoming everyone and treating everyone with love and respect, is alive and well.  This isn’t just something you see while you’re on vacation or on honeymoon.  

The people living there do embody that aloha spirit.  We had locals offer to help us move (they came by even when we declined initially), and we had locals invite us to their luaus.  We experienced the aloha spirit first hand.  We will never forget the wonderful locals who made us feel welcomed...
  • Seafood, seafood, and more seafood!
Because Hawaii is a series of islands, you’ll have plenty of seafood options!  As mentioned previously, mahi mahi (dolphin fish), ono (wahoo), shrimp, are everywhere in Hawaii.  We loved Roy’s Restaurants in Hawaii Kai (Oahu), Giovanni’s Shrimp Shack, Kua Aina Burger, etc.

Most local restaurants should have some fish on the menu.  Be sure to try them!
  • Local food and food from around the world!
You must try local ‘plate lunch’, which is two scoops of rice, protein of your choice (fish, shrimp, pork, or beef), and a side of mac (macaroni) salad.  These are relatively cheap to buy.  Try L&L Hawaiian Barbecue or any of the other local joints!

Because island of Oahu is literally translated ‘the gathering place’, there are people living there from everywhere in the world.  This benefits the food connoisseur as every type of cuisine is represented in Oahu!

We had some of the best Italian food, Indian food, Japanese food, and Chinese food (dim sums) anywhere!
You won’t go hungry living in Hawaii, that’s for sure.
  • Casualness (clothing)
You can probably get by on a t-shirt and board shorts for everyday of your life in Hawaii.  On formal occasions, you can just wear an aloha shirt and khakis.  

We certainly saved money on clothing while we lived there.  No more winter coats, suits, hats, gloves, etc.
  • Things to do

There are so many things to do in Hawaii.  You can do all kinds of watersports (surfing, wind surfing, snorkeling, swimming, boating, fishing, etc.), hiking, take ‘The Bus’ around the island to sightsee, Pearl Harbor/Arizona Memorial, Aloha Stadium swap meet, use Honolulu’s library (one of the best we’ve seen), visit the only palace (Iolani Palace) in the US, catch free hula dancing and music at any # of Waikiki hotels, and the list goes on and on and on...

  • Waikiki area

Waikiki Beach has so many things you can do.  There’s a zoo (Honolulu Zoo), world famous beach, world class shopping (and shopping for bargain hunters), people watching, different hotels (Hilton Hawaiian Village has free things to enjoy like penguin feeding shows for example), and Kalakaua Avenue, which is the main thoroughfare in Waikiki.

Catch a beautiful sunset with a drink in your hand at any # of beachfront hotels.  Some of the best ones are happy hour at the Halekulani Hotel, Outrigger Waikiki Hotel, Hilton Hawaiian Village, etc.

Take a dip in the ocean, learn to surf, or snorkel.  If you get hungry, grab food from the cheap (plate lunches), to 5 star restaurants.  Endless options are available...

  • Weather
Hawaii definitely has seasons.  There is the wet season between November through March, and a dry season between April through October.  During the wet season, the trade winds that cool the islands are gone for days, replaced by humid air.  It may also rain quite a bit.

Honolulu enjoys over 270 days of sunshine and the water temperature is mid 70’s to high 70’s.  It’s awesome vacation weather for most people.

Chinamans Hat, Oahu, Hawaii

Lanikai Islands, Oahu, Hawaii

Cons of living in Hawaii:

  • Cost of living
This is the biggest eye opener when you move to Hawaii.  When we lived in Waikiki for 4 months, we shopped at the only supermarket located in Waikiki, called Food Pantry.  We paid about $7 for a gallon of milk and about $4 for a loaf of Wonder Bread!

After awhile, we learned to shop outside of Waikiki area altogether.  We would go grocery shop at places like Walmart, Safeway, and other places.  Compared to most places, these were still expensive, but they were definitely less expensive than in Waikiki.  Examples:  a gallon of milk would be about $4 and a loaf of bread would be about $3.

Gasoline prices are some of the highest in the nation.  When we lived there, it was $4.50 per gallon, where as NYC was $2.50 per gallon.  Cost of car insurance in Oahu is usually high as there is a concentration of cars and people living in Honolulu (about a million people in Oahu).  

Cost of housing is one of the most expensive in the nation.  A studio or one bedroom condo costs around $200,000 and up, while homes cost on average $800,000.

Rentals are also very high.  Expect to pay on average $1900 for a one bedroom apartment in Honolulu.  

Once you move outside of Waikiki area, prices will be less, but not overtly so...The more interior you move to, the less the prices will be.  For example, if you live near Pearl City, or Aiea, the cost of rental should drop to about $1,200 and up.

  • Lack of good paying jobs
When considering moving to Hawaii, look into getting a job before you get there...We didn’t and we ended up working retail and/or transportation which pays close to minimum wage.  

Most jobs in Hawaii are related to the tourism industry.  Plenty of jobs are available in hotels, tour companies, transportation, but not so much well paying jobs with full benefits.  Be sure to research jobs prior to moving there.  *Note:  due to the pandemic, every state is suffering from job losses.  Hawaii is also feeling the pain right now.  Do your research re: available jobs...

  • Island fever or rock fever
I got island fever after living there for about a year.  It’s that claustrophobic feeling that you get realizing you’re surrounded by oceans on a tiny island.  I drove around the island one too many times after which I said, “This is enough...”

I love to drive and discover new places.  It’s one of my true passions in life.  When I couldn’t drive for hours and find new places, I got depressed... I got tired of driving around the island, in circles, after awhile...

I’ve met several men mostly, who said the same thing about living in Hawaii.  I took an unofficial survey of these men, and found they spent on average about 2 years before calling it quits.  I became that statistic.

It took me about a year to feel that, but we actually went back to the mainland after 2 years and 4 months.  If you’re considering moving there, seriously consider this feeling of island fever.  Unless you’re rich and can travel to other places few times a year, you may eventually hit a wall like I did...
  • Weather
Weather is both a pro and a con.  Coming from a four season climate like the northeast, it’s hard to adjust Christmas temperature hovering around 82 degrees in December.  After awhile, we missed the cold weather.  We missed the crisp cold winter day when we can see our condensation from breathing.

We missed looking at snow!  *Notice I said ‘looking at snow’.  I don’t like to go to work on a snowy day, or clean up snow!  I just like looking at it.
  • Family and friends
If we had grown up in Hawaii, then this would be a non factor.  However, for us, we missed them after about a year.  If we had money to go visit them every season, then maybe we would’ve been ok living there longer, but that wasn’t the case...

This is for me the biggest reason why we moved back to the mainland.  My wife would’ve been ok for another year or two, but even she admits, it would’ve been soon...

In conclusion:

Living in Hawaii was always our dream after our honeymoon.  We’re sure we weren’t the only ones who thought about, dreamt about, living in paradise.  We’re glad we followed our dream.

Even if that dream ended in little over two years, we’re always grateful for the chance to do what most people only dream about.  We’ll always remember the beauty and the aloha spirit of Hawaii.

We would love to visit Hawaii in the future, but as a visitor, and not as a ‘malihini’ (a newcomer).  Our memories there still make us smile...

If you too are thinking of moving to Hawaii, please consider these pros and cons in this post.  Thank you all for reading!


Wandering Money Pig 

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