Hawaii is truly an amazing, magical place. I was lucky to grow up there as a kid. It’s warm, safe and offers exotic scenery and activities. However, paradise comes with a cost. It’s expensive, small and a radically different lifestyle than what you grew up with if you were born and raised on the mainland. It can be a big adjustment for people moving here for the first time, and some may think that the opportunity costs are too expensive to commit to the islands full time. Some who move to the islands end up falling in love with it and can’t never think of themselves living anywhere else! So it works! But for some, it doesn’t work out. These are three reasons why Hawaii is not for everyone.
Reason #1 Why Hawaii is Not for Everyone: The Inability to Downsize.
Real estate in Hawaii is on average much smaller than places like the Midwest or East Coast. As you can think, it’s primarily because of the limited supply of it and unique terrain of the islands. The islands have mountain ranges all over them and it’s difficult to develop on most of the land. Hence, the properties here are smaller and more quaint. It can be difficult for someone who grew up in a large midwestern home to downsize their valuables and vehicles to fit into a small home on the islands. This can be an inhibiting factor for those trying to adjust to the islands. The ability to downsize can be more difficult than you expected.

Shining over the Central Fire Station downtown.
A full moon in downtown. by Daniel Ramirez is licensed under CC BY 2.0. Image may have been resized or cropped from original.
Reason #2 Why Hawaii is Not for Everyone: The Outdoor Lifestyle.
Growing up I thought everyone loved going to the beach and hiking and getting salty with the humidity. Come to find out, that’s not the case for everyone’s preferred outdoor activity. Some people enjoy urban centers with downtown nightlife and city living, and that’s great! But that’s definitely not going to be here in Hawaii. The outdoor lifestyle in Hawaii is also different than most outdoors. For example, there’s not much rock climbing, there’s no skiing and water sports are limited. For example, people don’t own boats for luxury here. The only people with boats are fishermen who need them for a living. The outdoor lifestyle in Hawaii is heavily centered around ocean life. For example, there’s little to no backpacking because there aren’t many trails that are extensively long (longer than 12 miles).

Shorebreak by Brian Burger is licensed under CC BY 2.0. Image may have been resized or cropped from original.
Reason #3 Why Hawaii is Not for Everyone: The Population Density.
The population density in the islands is one of the highest, almost a million people live on the island of O’ahu and most of them are concentrated in the city of Honolulu. That’s a lot of people. When relatives or friends come to visit the islands, that’s the first thing they comment on- look at all these people! Keep in mind this doesn’t include the heavy tourism industry that reaches its peak during the holidays and summer months. The traffic can be ridiculous because of this, which can be overwhelming for those who are used to living a simple rural lifestyle.

Lahaina’s busy Front St. by Matt McGee is licensed under CC BY-ND 2.0. Image may have been resized or cropped from original.
Need some information on where to buy a property – Maui or Big Island. My husband is a golfer. I love Mountain Views, hiking, going to the beach. Both of us are not surfers. We are both very active and I love being in nature and gardening. What would be ideal island for us to move? I am thinking initially we will buy a townhouse or a condo with ocean/Mountain View’s so when we are not there we can use that as a rental. Then when we are ready to retire, would like to move permanently. What are your suggestions? Thank you!
Aloha Jay and thanks for reaching out. On the home page there are great links including one to a very popular YouTube video “which island is right for you?” which I highly recommend. All the islands have what you want so you’ll have to dig a little deeper to see what’s right for you. This site has tons of content including real estate. Start on the home page and you’ll see what I mean.
By no means are we planning a move at this time, but my wife was very enthused after our first visit last year, so much so we are going back for another 2 weeks this Spring. She’s the one who brought up the possibility of doing “a future move” so we had to at least consider a few things. We have a moderately sized home now and a small (less than 1/4 acre yard). We know we would be unloading the majority of what we currently own were we to make a move, so a home smaller than what we have now is fine. What we would like is a somewhat larger lot. We spent our 2 weeks last year on Hawaii, stayed on the east side but went all over. Would be nice to have some space to grow things. We have more things growing in our current small yard than we saw in most lots in Hawaii. Also she actually likes the rain on the east side of the island.
As for crowds, we are really packed in where we live now, probably not much less crowded than on Oahu. If we were on Big Island I don’t see there would be an issue with crowds, at least not in the area we would probably choose to live in.
As for being outdoors, I am outside year round now every chance I get, even if its just to take care of all the stuff we have growing here. We are also 6 miles from the ocean. So an outdoor lifestyle which revolves around the ocean is what i would want.
Will see how she feels after this second trip.
Make sure you both watch my YouTube video on how family gets affected.
https://youtu.be/szKW9oNbnO8
The outdoor and downsizing issues do not necessarily apply to the Big Island. Larger 1500-3000 sq foot homes and acreage are certainly more affordable on the east side of the Big Island than the other islands, or for that matter, the Kona side. There are a number of hikes in HVNP that are great backpacks, with overnight camping. Likewise, the NE part of the island has some very challenging backpacks.
None of that applies to the big island.. Oahu (kuai possibly as well) is what this writer was thinking about.
I lived on the Big Island and while there are some differences, the core values are relatively consistent.
Pretty much none of this applies to the big island, where we live. There’s lots of room and home prices are affordable.
Perhaps on the population density side, but the outdoor and downsizing issues certainly apply.