Moving to Hawaii
The Complete Relocation Course
6 weeks to prepare for your new life in Hawaii. It is free, it is live, and it is honest about the dream and the logistics.
Learn
Six weeks on choosing an island, buying a home, taxes, healthcare, shipping your life over, and settling in. Watch it or read it.
Meet
Go through it with a cohort planning the same move. Live sessions, real questions, and people who stay in touch long after week six.
Get Help
A local network you can actually use for moving, housing, lending, and everything else the move throws at you.
Start Here: Aloha and E Komo Mai 🤙
Important Message from our Founder, Peter Kay ❤️
Fall 2026 cohort
The six weeks, and when we meet
Each week opens on a Sunday, so you can watch and read on your own time. Then we get together on Zoom Saturday morning to talk story, ask questions, and work through whatever came up that week.
October 2026
November 2026
Sat Oct 24 and Sat Oct 319:00 am Hawaii · 12:00 pm Pacific · 1:00 pm Mountain · 2:00 pm Central · 3:00 pm Eastern
Nov 7, 14, 21 and 289:00 am Hawaii · 11:00 am Pacific · 12:00 pm Mountain · 1:00 pm Central · 2:00 pm Eastern
What past cohort members say
From earlier cohorts of this program, hosted by Peter Kay.
“There is a lot to think about and do in planning a move to Hawaii. The experiences that Peter shares make a great deal of the process easier. There are things that I never would have thought about. Peter’s open and honest lessons will make you think and will save you time and frustration. Beyond what Peter teaches he binds the Ohana together and makes each member feel comfortable sharing their experiences.”
— Judi W.
“Joining the Hawaii Islander Transformation Program has given my family the confidence and resources to make this dream a reality. Connecting with a cohort of other like-minded individuals going through a similar process has been incredibly rewarding. The cultural, financial and practical lessons give you all of the tools necessary to see if Hawaii is right for you.”
— Kinaya
“I would recommend the Islander Ohana to anyone considering moving to Hawaii. Peter Kay shares practical tools, candid advice, and his own real-life experiences. The combination of course materials and cohort interactions have been invaluable to our family and helped to reaffirm that this is the right move for us.”
— Jody
“I would never want to move to Hawaii without first being part of Peter Kay’s Islander Ohana group. It’s so amazing to have gained information from Peter and others in the group. I look forward to the meetings and classes and just can’t get enough. I’ve gained Peter and a group of people who feel like ohana.”
— Scott
“Peter’s Hawaii Islander Transformation class has been a priceless experience for us. One huge benefit of Peter’s wisdom is that it helps manage expectations. Now, instead of having unrealistic expectations that would have come crashing down, we are ready to make our move to Hawaii with eyes wide open.”
— Jessica
“To be honest, when I first heard about this cohort course, I was intrigued but also wary. I’m glad I took a chance. Many of the things you talked about were things I’d noticed about Hawaii during my visits, but it was helpful to have you consolidate these observations. You confirmed things about Hawaii and its culture that I thought I saw, but wasn’t sure I was interpreting correctly.”
— Mark
Most people who move to Hawaii end up moving back home
And some of the biggest reasons for failure…
- Never get hired
- Can’t afford it
- Get overcome by loneliness
- Reject (or get rejected by!) the culture
- Find out it wasn’t meant for them in the first place
You can’t “get it” by just reading blogs and watching videos. You need to:
- Follow a roadmap that will transform your life and embrace local culture
- Connect with a network of people that support each other
- Talk to employers who will take you seriously
That is exactly what this course is built to prevent.
Six weeks, one topic at a time, in the order you actually need it. Which island fits you. What homes really cost here and how the financing differs. Taxes, healthcare and retirement math. What to ship, what to sell, and what to do about your car. Then culture, community, and your first ninety days.
Nothing is sugarcoated. You will hear about the pay cuts, the shipping bills, the rainfall and the vet waitlists right alongside the reasons people stay for good.
Your host
Nancy Miller
Nancy hosts this cohort, and she made this move herself not long ago.
She was in a third-floor condo in San Diego with bay views and had simply had enough of concrete. She looked at Oahu first and decided that if she moved there, she might as well have stayed in San Diego. She landed on the Big Island instead, where the feel of the place clicked and her California money went a great deal further.
From decision to moved in took about nine months. She picked the island first, listed the condo, flew out to look at homes as soon as it went into escrow, bought one, and closed in forty-five days. She brought two cats across the Pacific, and she moved into an empty house, where she spent her first two nights in an Airbnb because she did not own a bed yet.
She swims in the bay three days a week now, rarely eats dinner indoors, and plans to retire here. Every week of this course is something she has already done, including the parts that went sideways.
Six weeks changes the odds
Most people arrive here hoping. You can arrive knowing.
It is free. Here is why.
We make our living helping people buy homes in Hawaii, not selling courses. If this helps you decide Hawaii is right for you, we would like to be the people you call. If it helps you decide it isn’t, you just saved yourself years and a great deal of money. Either way it costs you nothing.
What comes with it
All of this is included. There is nothing to buy and nothing to upgrade to.
Live sessions with your host
Six weeks of live meetings. Bring your questions, and hear what everyone else in your cohort is running into at the same stage of the move.
Written lesson notes
Every lesson is written out as well as filmed, so you can read instead of watch, and come back to a detail later without scrubbing through a video to find it.
The financial planning worksheet
A checklist and a calculator in one. It gives you a clear monthly target for what living here would actually cost you, before you commit to anything.
Our local partner network
Agents on every island, lenders who understand Hawaii property, and the movers and shippers we use ourselves. Introductions when you are ready for them, not before.
The alumni group and monthly talk story
Finish the course and you are in. A private group of people serious about this move, plus a monthly talk story where you can ask anything of people who already live here.
What we ask of you
The course is free, so there is nothing to refund and nothing to cancel. What we ask for instead is your attention.
Show up, do the homework, and be honest with yourself about the answers. The people who get the most out of this are the ones who let it change their plan, including the ones who finish and decide Hawaii is not for them. That is a real result, and a far cheaper one than finding out after you arrive.
This works best if you
- Take the weeks in order, because each one builds on the last
- Do the homework, including the parts that are uncomfortable to look at
- Bring your real numbers to the financial week, not your optimistic ones
- Ask your questions in the live sessions instead of guessing
And if you finish and decide to make the move, tell us. That is the point where we can actually be useful.
You will not do this alone
Every cohort goes through it together, and the group stays in touch long after week six.
Ready to find out what it really takes?
Six weeks, live, and free. Follow the join button to get your spot in the next cohort.
What six weeks gets you
- A real answer on whether Hawaii is right for you, instead of a guess
- The right island, and the right side of it, for the life you want
- Honest numbers on homes, taxes, healthcare and monthly costs
- A move plan with dates on it, not a someday plan
Most people research this move for years and still arrive unprepared. Six weeks with someone who has already done it will get you further than all of that reading.
Join the CourseQuestions about the course
Clear answers to the things most people want to understand before joining.
Is this course right for me?
If you are seriously considering a move to Hawaii and want a clear, step-by-step way to think it through, then yes. If you just want to daydream about it for now, enjoy our free content on LivingInHawaii.com and our YouTube channel, and come back when you are ready.
How much does it cost?
Nothing. The course is free. We are a real estate team, not a course business. We would rather help you decide well now and be the people you call when you are ready to buy.
Do I have to be sure about moving to take it?
No, and most people are not. Week one exists specifically to help you answer that question honestly. Deciding not to move is a perfectly good outcome.
Can I read the lessons instead of watching them?
Yes. Every lesson has full written notes alongside the video, so you can read at your own pace, skim back to a detail, or go through it on a plane with no wifi.
How long do I have access to the lessons?
You keep access to the lessons and the written notes. Finish the course and you also get into the alumni group and the monthly talk story, for as long as you want to be there.
What are the meetups?
We hold live ‘Ohana meetups in Hawaii. These are member gatherings where you meet other people from your cohort in person and turn online connections into real ones.
What actually happens on a live call?
Nancy opens with whatever came up in that week’s lessons, then it is mostly your questions. People ask about their own situation, their island, their numbers, their timeline. You hear what everyone else at the same stage is running into, which is often the most useful part.
Do I have to be on camera?
Yes please. This is as much about meeting each other as it is about the lessons, and it is hard to build a friendship with a black square. Cameras on is what we expect, and most people find the group turns out to be the best part. The calls are recorded and posted in our private group afterward, so you will appear there too.
Do I have to talk, or can I just listen?
Just listening is completely fine. Plenty of people stay quiet for the first week or two and then start jumping in. Nobody is put on the spot.
What time are the calls, and why do the mainland times change?
Every call is 9:00 am Hawaii time, all six weeks. Hawaii does not observe daylight saving, so our time never moves. The mainland sets its clocks back on November 1, which means that from the November 7 call onward the same class lands an hour earlier on your clock. We will remind you.
What if I cannot make one?
Every talk story is recorded and posted in our Facebook group afterward. We hope you make all six and take part, because that is where the course comes alive, but life happens and the recording is there.
Is Zoom going to be complicated?
No. It is the same link every week. You click it and you are in. If you have never used Zoom, say so in the group and someone will walk you through it before week one.
What happens right after I sign up?
You get one email asking you to set up a login, which takes about a minute. That is the only thing to do before October 18, when the first week opens.
Is this really free, or is it a pitch for your real estate services?
It is free, and there is no upsell inside it. We are a real estate team on these islands, so yes, we hope that if you do move you will call us. But week one is built to help you decide honestly, including deciding not to come. Nothing in the course is gated behind a conversation with an agent.
How much time does it take each week?
A handful of short lessons you watch or read whenever you want, plus the Saturday call. You set the pace on the lessons. People with busy weeks tend to batch them on a Sunday.
Can my spouse or partner go through it with me?
Yes, and we would encourage it. This is a decision most people are making with someone else, and the week one conversation works much better with both of you in it.
I already live in Hawaii and I am thinking about a different island. Is this for me?
Parts of it, yes. The island fit, cost and logistics weeks are useful for an inter-island move. You can skip what you already know, and the Saturday calls are a good place to ask the specific questions.