I moved to Hawaii and you can too. Here’s what you need to know….


The move to Hawaii can be taken lightly, or with annoying amounts of obsessing.  I chose the latter method.  If you are a youngin‘ just out of high school, or college, go ahead and grab your backpack and one checked bag, and go crazy exploring the island life.  Be prepared to turn vegan involuntarily due to the cost of food, and be open to sharing your pad with other like-minded would-be surfers and free spirits, who come here, change their names to Harmony and practice some sort of energy healing.

If you are over sixty and looking for more of a retirement experience, make sure your backpack is full of money, cause you are gonna need it!  Also, make sure you don’t have any major health problems, as some of the health care options can be pretty sparse on some islands.  That being said, Hawaii is one of the healthiest places on the earth, where people tend to stay active well into their 90’s or beyond, and happily “above-ground”, much longer than anywhere else in the U.S., statistics show.

If you are retired military, Oahu may be the better choice for the 60+ crowd, as you can take advantage of the PX and Commissaries on island too, as well as better and more health care options.   If you retired with full benefits, you will have easy access to free healthcare, of course.  While all this is a strong pull towards Oahu, you will have to tolerate some of the worst traffic in the country.  Metro rail is currently under construction there.  We are hopeful that it should ease some of the traffic congestion.  In the meantime, many workers spend 1-2 hours in traffic each way commuting to their jobs.  So, you’ll have to do your shopping/errands when that commuter traffic is not at play.

If you are older and in love with the less populated islands, realize that people commute via air to Oahu for health care procedures, all the time, and often in less time than some folks do on the mainland in cars.  We have Kaiser Insurance and have had to do this a couple of times for procedures not available on Maui.  They pay for the flight, for yourself and one companion usually, and shuttle you to the Kaiser Hospital from the airport, which is a nice benefit.

I’m a Washingtonian by birth.  We are blessed with amazing health care there and awful, awful traffic problems.  One bonus is that the Washington metro area is full of educated folks.  We talk a lot and take everything a bit too seriously.  Politics, history, government surround you there, like the invading hordes.  It’s difficult to shut all that out, to be honest.  It you are obsessed with these sorts of subject matters, after a few years in Hawaii, you may long for easier access to the NY Times, a bagel and a smear, over truly good coffee…or the sort of cocktail parties you used to attend with other like minded, educated, well-informed folks.  Not for nothing, but most people in Hawaii care little about politics.  If you are a pol junky, stay on the mainland cause the isolation here may make you feel literally and figuratively adrift at sea.

I must admit, I do sometimes miss living on the east coast.  While the weather is amazing in Hawaii, there is something about the reality of four seasons that gives everyone a common bond and something to talk about.  My home town of D.C. is definitely a lovely part of the country.  Driving downtown at night, among the monuments and Greek architecture-inspired buildings is a sight to behold.  DC is blemished usually only by the month of August, when the humidity destroys all life as you once knew it, though with global climate change, the nasty season is lengthening, as are the rougher winters (as kids we prayed for snow and rarely got it.)

As a Washingtonian, used to heat and humidity, I found Maui much easier to deal than my husband, a CT yankee ….well, at least until menopause hit.  Then, it got a little dicey.  So, I moved from Kihei (the hot side of the island) to Wailuku, where the weather is near perfection and cured that little problem overnight.  The trade winds make all the difference here and the altitude is everything.  We are about 600 feet above sea level which is so lovely weather-wise.  If you still want the feel of four seasons, the cozy nature of a fire place at night, maybe look for real estate up country in Kula (on Maui), or Kamuela (Big Island), for instance.

The bottomline is this.  If you like to be in the thick of things, where it all happens, Hawaii is not for you.  It’s as close to living in another country, while still being in the U.S. as you can get.  Just watch our local news, when you visit and you will see what I mean.  In truth, it’s more about the local experience, rather than national headline news and, frankly, most people like it that way, though political junkies like me jones for other realities.

For me, the first real consideration when moving to Hawaii should be the weather.  Are you going to miss the vast variations from hot to cold?  Do you already live in a hot area and feel adjusting to Hawaii should be pretty easy?  Of course, the Hawaiian Islands consist of eight main islands in the State of Hawaii (Hawai’i, Maui, Lana’i, Moloka’i, Kaho’olawe, Oahu, Kauai and Niihau), though there are a total of 137 islands and atolls altogether, mostly uninhabitable.  Some areas are prone to flooding.  Some struggle with the effects of VOG, the gases that come your way off the volcanoes, if you live on the Big Island, and some parts of Maui, mainly.  You gotta listen to the weather reports to know which way the wind is blowing, though if you keep your windows open at night, figuring out if it’s a Claritin day or not, should be pretty easy.

Weather has a big presence in Hawaii, with first of the month Tsunami warning horns (and incoming missle alert, recently added, though I can’t remember which is which…really should look into that one of these days.) The need to always be prepared with medicine, food, water, etc…in case of a weather emergency.  They say there is only a 2 week supply of food in the islands….which is totally crazy, since we have the perfect climate for growing just about anything.

People do tend to help each other out (the necessary interdependence of island life.)  If rains and winds take down trees that block the roads, locals usually get out their chain saws and get busy, long before government types show up.  Any power outages that happen are usually dealt with quicker than I’ve experienced on the mainland..  You will find that the weather is a frequent topic of conversation here,  as it is on the mainland, and getting the surf report from our weather man Guy Hagi, is really one of life’s joys that shouldn’t be missed.

When picking your island, realize that there are really quite a lot of weather variations here.  Though we have some of the most beautiful weather in the world, please research the areas that interest you and travel there at different times of year.  Do your research, since Hawaii has 9 to 10 of the world’s 14 climates in the world.  (See: https://www.hawaiimagazine.com/content/hawaii-has-10-worlds-14-climate-zones-explorers-guide-each-them)

You will want to factor in whether you care for, or need (due to health reasons), a drier zone.  A wetter zone, like Hilo, may have a tendency to flood, or have mold issues.  The physical beauty of the greener/wetter zones can be quite astounding.  You can raise your chickens and organic garden there, with little effort.  In the desert areas, like South Maui, you may want to pull out your grass, if you don’t want to spend a fortune on watering everyday and lay down lava rock (which can be quite beautiful too), and plant drought-tolerant plants.  The sunnier/drier areas tend to attract more tourists of course, so if that’s a consideration, you may want to avoid those areas, or look for a happy medium, between wet and dry, which all islands have.  It got a little tiresome for us, living on the touristy side of time, due to the traffic that lolly-gaggers induce.  That being said, if you are going to start your Hawaiian Island journey as a renter, be spontaneous and go where the vibe draws you in, or if I’m being perfectly honest, where you can find a place, as rental properties are often hard to find and have many interested takers.

If you fall into the 30-something to 50-something crowd, with kids, make your decision with more caution and consideration.  In many cases, you will need to put your child in a private school, especially if they are gifted and talented as ours was/is, or the college-bound sort.  We initially started by putting our daughter in a public charter for the first three years.  The first two years were acceptable.  The transition to middle school was pretty bad, in terms of control of the classroom and general disorganization.  There also seemed to be more personal problems in the kids’ lives that found their way into the already dramatic nature of middle school life.  We switched to a Catholic school for 7th and, though initially quite happy with the school, found those kids had some seriously side lives as well.  Private education in the islands comes at a premium , costing anywhere from $10,000-over $20,000 annually.  We defray the costs as we own a Ohana (cottage) on our property that we rent out.  If you haven’t put any savings away for your kids’ college and you know they are the sort to want to go, that fact alone should be considered seriously before moving here.  Once you get here, the cost of living is so high, it will become increasingly difficult to put away money for such an expense.  It may be better just to stay on the mainland and live a less beautiful life, in favor of stability.

If you do come here and buy a proper, realize that about a quarter of all home owners in Hawaii have an Ohana.  It is an excellent way to subsidize your living.  Some folks rent out their Ohana through Airbnb and other companies, which is both lucrative and controversial, as it does eat into the local housing market.  (There is an ever-growing population of homelessness in the islands.  Efforts are being made to build more affordable housing, but it will be sometime before supply catches up to need.  There is a significant drug problem here too, which leads to homelessness and crime.   If you can find a property with a decent Ohana to buy, that you like, jump on it.   Just do a thorough background/credit check on any potential renters.  This seemed so intrusive to mean as an East Coaster, but it really is a must, if you want to try to avoid some of the social problems that exist in the islands to enter your personal realm.

So, education is a main consideration, for sure.  If you are a home-schooler, then the sky’s the limit.  Live where your heart tells you to live!  To find out more about this option, check out: http://hawaiipublicschools.org/.   Beyond public schools, again know that there are many wonderful private schools in the islands.  (Though in the wealthier residential areas like on Oahu, to be honest, your child can often attend the public schools and sit next to the sons and daughters of the movers and shakers on island, and get a quality education.  There is the apple doesn’t fall far from the tree factor.  These children often have parents with high expectations of them, which raises the level of the classroom.

But what do you do if living in a wealthy area is not an option for you, but you still can’t get Hawaii out of your head.  If you are a talented fixer upper sort, you could buy a distressed property in one of those rich neighborhoods, do the work, live in it for a while, then sell for a nice profit.  Again, buying a home with an Ohana can really open up options for you.

What many, even wealthy folks do is put their kids in public schools, or less expensive private schools until high school, then apply and transfer them to one of the college prep schools.  These are often very competitive institutions though, with demanding entry requirements, as well as limited openings.  This is what President Barack Obama did after all, as he is a graduate of the elite institution, Punahou School (https://www.punahou.edu).

Just know that your child will need great grades, test scores and extra-curriculars, and interview well.  Fortunately, most private schools have very generous, often full-tuition scholarships for the students in need, who they want in their school.  If your kid is one of those sought after kids, a full-ride may be in your future.  So, while schooling can be a challenge in Hawaii, if you are a dedicated parent, who loves to do your research and get the scoop on the real deal, you will probably do just fine here.

We found it was best to talk to local people for recommendations too.  They know what’s what.   While it may be hard to tear yourself away from the beach on vacation, I would schedule some school interviews with the schools you are considering in the areas you are drawn to.  While most private schools here schedule open houses twice a year (and if your vacation syncs up with them great, take a few hours and go), many schools will meet with you individually and, even, schedule interviews and testing for your child.  I highly recommend subscribing to Honolulu Magazine, as this publication is both beautiful, fun and informative, but has an annual private school review of all the islands.  It is really an awesome issue!

Finally, weather and schooling aside, are you passionate about these islands, because that’s really the only thing that matters and the only thing that should bring you here in the first place.  Do you want to become a part of these islands, because transitioning can be hard?  Being true Kamaaina (a local) is more than getting a Hawaii driver’s license.  Locals are reticent to get to know outsiders, for many reasons (from culture, to race, to just the sheer fact that we often leave, after a year or two).  Heck, they even have a term for us, “Haole”, which doesn’t have to be, but is often used in a pejorative way.  Being a perpetual outsider after living here a few years is a distinct possibility, one that may lead you (like it has many others) to go back home.   So, strongly consider the experiences of other transplants, before coming here.  You may find it’s a great place to vacation, visit or live for awhile….yet, ultimately, too hard to stay, for the rest of your life.  You may long for that sense of home, the familiar patterns of a life you once knew, a culture that is more in sync with your own.  Hopefully, some of what I have written here will help you in making the decision for you and yours.

Stay Beautiful and Sassy!


Mrs. Sassy Pants


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