Should You Move to Hawaii?

I almost moved to Hawaii. Twice. The first time was sometime around 2010 — Kauai, my favorite of the four main islands, the one whose energy I'd been chasing since 2002. I had a plan. I had a list of houses. I had researched schools, drivers' licenses, the cost of a gallon of milk, what it'd take to ship our cars over, and how long it'd realistically take to build a freelance income that didn't depend on East Coast clients. The second time was a few years later, with a slightly different plan and a slightly different version of me.

Both times, I didn't go.

This piece is the honest version of why. Not the romantic version, not the bitter version, not the cautionary version — just the version I'd tell a friend who showed up at my door tomorrow and said "I think we're moving to Maui. Talk me through it."

If you want the practical relocation logistics — pets, cars, costs, what to ship vs. sell — start at the main moving guide. The five linked pages at the bottom of this essay are where the spreadsheet work lives. This piece is the part that comes before the spreadsheet, when you're still trying to figure out whether you actually want what you think you want.

The fantasy that drives the question

Almost everybody who seriously asks "should we move to Hawaii?" is asking some version of the same question underneath, and it's usually not "can I afford it?" The real question is closer to "can I make this feeling permanent?"

The feeling, if you've felt it, is hard to forget. You stand at the rim of Haleakalā, or on the bench at Waikamoi, or watching the sun drop into the Pacific from Kamaole III, and something inside you slows down for the first time in years. You sleep better than you have in a decade. You read books on the lanai. You eat papaya for breakfast. The Myna birds are loud and you don't mind. By day five, you're already thinking about how to extend the trip. By day seven, you're thinking about how to never leave.

The fantasy is that if you just moved here, that feeling would become your default state. That the version of you who exists on day five — relaxed, curious, present, easy in your own skin — would just be Tuesday.

That's the part that almost never works the way you think it will.

What actually happens when you move

The relaxed-curious-present version of you on day five exists because you're on vacation. Take that away — give yourself a job, a commute, a mortgage, a leaking water heater, a kid who needs a dentist appointment, a parent in declining health on the mainland, a small-business client who keeps changing the brief — and the day-five feeling goes wherever it goes when you're at home now. Which is to say, mostly nowhere.

This isn't unique to Hawaii. People who move to the Rockies for the skiing find themselves working long hours in a cubicle. People who move to Tuscany for the wine end up dealing with property tax disputes in Italian. The "place" you fell for and the "place" you live in are not the same place. The first one is a vacation overlay. The second one is the underlying reality, and the underlying reality is where you actually have to live.

For Hawaii specifically, that underlying reality has some sharp edges that hit harder than people expect:

• Cost of living. Hawaii is the most expensive state in the country and it isn't close. Median home prices on Oahu and Maui regularly clear seven figures. Groceries are 40-60% above the mainland average. Electricity is the highest in the country. Even a "modest" lifestyle here requires a real income or real savings, and a lot of mainland transplants underestimate this until they're three months in.
• Distance from family. A trip back to see parents or grandkids on the mainland is a five-to-ten-hour flight, often expensive, often a multi-day commitment. The funeral you can't get to in time. The grandkid's birthday you have to FaceTime. The aging parent who needs more help than you can give from 2,500 miles away. This one ages people fast.
• The local-vs-transplant social layer. Hawaii has a real local culture, with a real history of being colonized, displaced, and now economically pressured by the same wave of mainland money you'd be arriving on. Locals are mostly very kind. They are also mostly aware that "we're moving here" from a mainlander often means another house off the market for a local family. The most successful transplants understand this from day one and adjust their behavior accordingly. The least successful ones never quite figure out why they don't feel as welcomed as they expected to.
• Weather monotony. This is the one almost no one warns you about. Hawaii's weather is famously perfect — and it's the same kind of perfect, year after year, in most of the populated parts of the islands. Some people thrive in that. Others, after a few years, realize they actually miss seasons. The first cold morning back in October on the mainland feels like coming home in a way that surprises them.
• Island fever. Most islands are about the size of a single mainland county. After a few years, some people start feeling boxed in — same drives, same beaches, same small-town infrastructure, same six-degrees social network. It hits some personalities harder than others, but it's a real thing and it's a real reason long-term residents leave.

None of this means moving to Hawaii is a mistake. Plenty of people move and never look back, and they'll tell you it was the best decision of their lives. But the version of the question worth asking yourself is not "do I love Hawaii?" — almost everybody who's been here loves it. The version worth asking is "would I love LIVING here, in the actual day-to-day of it, more than I love the idea of it?"

For some people, yes. For a lot of people, the answer is some shade of "I love it more as a place I get to come back to than I would as the place I have to be."

Why I didn't go

I'll tell you the short version of my own decision because it's the version I trust most.

The first attempt, around 2010, fell apart for the obvious reason: I underestimated what it would take to support a Hawaii cost of living from a freelance income built around mainland clients. The math, when I actually did the math, was uncomfortable. I shelved the plan and kept going as a visitor, telling myself it'd happen eventually.

The second attempt was harder. By then I had a website that worked, a partner in Tori who feels Hawaii the same way I do, and a much clearer sense of what kind of life I wanted. We were closer to making it work financially. The list of houses got real again. The conversation with friends about "so when?" got more concrete.

And then a few things happened, in no particular order. The world changed in ways nobody saw coming. Family situations on the mainland got more complicated, in the way they tend to as your parents and your partner's parents get older. The economics of running an independent web business got harder, then easier, then harder again, then completely upended by the AI wave. Each individual factor would have been navigable. The combination kept tilting the equation toward "later, not now."

And then — the part that surprised me most — somewhere along the way I noticed I'd quietly built a version of life on the mainland that worked. Not the version I'd imagined, but a real one. An Oak Grove of nearly a hundred trees in central South Carolina. A Hawaii garden in the side yard with plumeria, hibiscus, and ti plants. Hearts of Aloha lotion on the bedside table so the smell of Hawaii is the last thing I take in before sleep. A loop where I keep going back to the islands every twelve to twenty-four months, the trip itself becoming the structure I plan everything else around.

Hawaii didn't stop calling. I just got better at hearing the call without confusing it with a moving van. The longing turned out to be the gift, not the problem to be solved. The trips back, with the months and seasons of anticipation in between, are how the relationship lasts.

Who I do think should move

I want to be clear: I'm not anti-moving. There are people for whom the move is right, and you can usually tell from a few signals.

You should probably take the move seriously if:

• You've already done a long stay. Not a vacation. A real, six-week-or-longer stay where you grocery shop, do laundry, get cabin fever for a day, find a coffee place where they recognize you, deal with the wifi outage, and survive at least one full week of "ordinary." If you got to the end of that and still wanted more, that's signal.
• Your work is genuinely portable. Remote-first job with a salary that maps to mainland rates, a creative business with non-Hawaii clients, an online income, a pension. Hawaii's job market is small and the wages don't keep pace with the cost of living for most fields, so importing your income is the cleanest path.
• You have low or no obligations on the mainland. No aging parents that need you. No kids whose lives anchor them somewhere. No business that requires regular in-person contact. The fewer threads pulling you back, the cleaner the move.
• You've thought hard about what you'll lose. Not just gain. Lose. Family proximity. Mainland career mobility. Seasons. Some friend group. Some sense of being from somewhere you can drive across. Make a list. If you can read the list and still want to go, that's signal.
• You're moving toward something specific, not away from something general. "Hawaii because of the ocean and the trade winds and the specific community I want to build in this specific town" works. "Hawaii because I'm tired of my life and I think a beach will fix it" almost never does. The beach won't fix it.

If most of those check, the move might be the right call. If they mostly don't, the visiting model is probably better — and that's not a consolation prize.

The visiting model is underrated

Here's the thing nobody told me when I was 28 and planning a Kauai move and assuming it was the only "real" way to do this:

You can have an extraordinary, life-shaping relationship with Hawaii as a frequent visitor. You don't have to move to take it seriously.

The math, even from the mainland, is much friendlier than people think. A trip every twelve to eighteen months, planned thoughtfully — flights booked early, condo over hotel, rental car through Discount Hawaii Car Rental, groceries from Foodland or Costco, a few standout meals out instead of three a day — runs a fraction of what relocating costs and gives you most of the actual experience of being there. Run the numbers in the trip cost calculator and the answer is usually less than people fear.

Twenty-four years of doing exactly that taught me the visiting model has its own gifts the moving model doesn't:

• Anticipation. The two months before a trip, when you're picking the island and rebooking the car and planning the dinners, are part of the trip. People who live in Hawaii lose this. People who visit Hawaii get to have it again and again.
• Distillation. Two weeks of Hawaii is enough time for the place to do its work without enough time for the daily friction to set in. You leave with the good version intact.
• Re-entry as compass. The first week back home, the contrast between Hawaii-self and home-self is sharp enough to teach you something about the rest of your life. People who live in Hawaii don't get that contrast — Hawaii becomes their baseline, and the calibration disappears.
• Permission to be a guest. When you're a visitor, the relationship is structurally honest: you came to be there, you'll leave. That honesty makes it easier to be a respectful guest, and being a respectful guest is the version of being in Hawaii that earns you the deepest version back.

I'm not saying the visiting model is universally better than the moving model. I'm saying it's a real model, and it deserves more credit than it gets in the "should we move?" conversations I've watched friends have over the years.

If you're going to do it anyway

If you've read all of the above and you still want to move — good. The honest stress test is part of how you make sure the answer is real. Here's what I'd tell you to do next, in this order:

1. Do the long stay first. Six weeks minimum, ideally longer. Off-season if you can — June to September is high tourist load and a misleading sample. Pick the island you think you want, rent something modest, and live like you live, not like you vacation.
2. Run the actual cost numbers. Use the moving cost calculator to estimate the relocation. Then run a real monthly budget — Hawaii rent or mortgage, Hawaii electric, Hawaii groceries, Hawaii car insurance, Hawaii everything. Check it against the income you'll actually have on island. The first big surprise is almost always the gap between what you thought it'd cost and what it actually costs.
3. Plan the practical logistics. Pets — start the quarantine and direct-release process months in advance, not weeks. Cars — read the shipping guide and decide whether shipping or selling-and-buying-on-island is the better play for you. Belongings — start the brutal what-to-keep, what-to-sell, what-to-ship triage early. The moving-to-Hawaii checklist is the page that walks you through this end-to-end.
4. Have a back-out plan. Not because you'll need one, but because having one removes the pressure to pretend everything's fine if it isn't. Six-month checkpoint, twelve-month checkpoint. Write down what "this is working" looks like and what "this isn't working" looks like, BEFORE you move, while you can still think clearly.
5. Show up as a guest, even after you arrive. The transplants who do best in the long run are the ones who never lose the awareness that they came to a place that was already there before them. Tip well. Drive slow. Learn the language. Volunteer locally. Stay humble. Hawaii rewards that posture in ways that compound over years.

And then — go. Try it. The risk of trying and discovering it wasn't right is much smaller than people think. You can always move back. The risk of not trying when you genuinely should have is heavier.

For everyone else

For the rest of us — the people who love Hawaii deeply, who feel called by it, who can't quite shake it, but who, on honest examination, have lives that work better with Hawaii as the recurring trip than the daily address — there's nothing wrong with that answer.

I tell myself this on the trip back, every time. The longing is real. The longing is also part of the relationship. The two months of anticipation before each trip, the careful planning, the quiet ceremony of the first morning back on island, the painful goodbye on the last drive to the airport, the way the smell of plumeria sneaks up on you in the side yard at home in mid-July and stops you for a full minute — none of that exists if you live there. Different shape of love. Not lesser.

Twenty-four years of going back, and the place still does the work it does. I get to keep visiting. Hawaii gets to stay Hawaii. And somewhere in central South Carolina there's a small Oak Grove and a Hawaii garden quietly holding the rest of the year together until the next trip.

I think that's the right answer for me. You'll find your own.

Aloha y'all,
John