Picture of Hawaiian Sunset

Hawaii Trip Report

Learn, Share, and Aloha!

For Our visitors, Residents, & future residents!

Follow us on twitter
Home Trip Reports Chris' Blog F.A.Q.'s Contact Us The Islands


 Big Island Activities

 Oahu Activities

 Maui Activities

 Kauai Activities

Site Seeing 

 Big Island Site Seeing

 Oahu Site Seeing

 Maui Site Seeing

 Kauai Site Seeing

Hotels / Resorts 

 Top Five Resorts

 Big Island Resorts

 Maui Resorts

 Oahu Resorts


 Big Island Restaurants

 Maui Restaurants

 Oahu Restaurants


 Big Island Beaches

Picture Gallery 

 Mauna Kea Summit

 Waipio Valley

 Pololu Valley

 Hapuna Beach


 Volcano - Kilauea

Moving Here 

 Moving To Hawaii

 Planning Your Move
 To Hawaii

 “Pre-Leave” Planning
 On Your Move To

 Travel On Your Move   To Hawaii

 Setting Up Shop  

 Getting Your Stuff

 Best Practices

 Mistakes To Avoid

 Big Island Resources


 Big Island Businesses


Planning Your Move To Hawaii

Planning To Move

I’m not the most organized guy, but even I stayed discipline with this phase of the move. It’s also the most challenging and can be very frustrating. Hopefully I’ll help you cut some corners with the planning phase.

A few things you’ll need for this phase:

1) A nice, large desk calendar. (Computer calendar may work for you also, but I really liked having the actual paper calendar out on our desk for everyone to see all the time.)

2) Computer and internet connection to help with your research

3) Complete, open communication with your spouse and/or family.

4) Patience

5) Method to organize all your numbers, addresses, budget, etc. I used pen and paper, but you may prefer a contact management program. My Outlook Express also helped with important email addresses. I’ve since started using Microsoft Works Projects, which is pretty cool.

6) Post it notes, scissors, desk supplies

I prefer to work within timelines, so I grabbed 4 pieces of typing paper (8.5 x 11”) and taped them together long-wise, so that I had a 44” wide chart to look at each day. (I’m very visual.) You may choose to use Office or some other calendar-based computer aid. I’ve used this paper idea for many years for important projects. Paired with a good calendar, it presents a nice timeline and visual check-off as you complete items. Here’s a picture of one that I’m using right now for our new Vinyl Banner business.

Planning to move to Hawaii

So in your planning mode, here’s the most important part: You need to determine your “drop-dead” move date, even if you have to adjust it SLIGHTLY when the time nears. We picked December 10, 2007, even though we had NO idea how we would be able to hit this target. Our situation may be a little more complicated than yours: We owned two small businesses and 11 residential and rental properties. Now please don’t think I’m rich. I’m not. We barely make the monthly payments on these properties and I can assure you that we didn’t have thousands of dollars lying around to make the move with. You may need to sell your home, or turn-in a resignation, but the “take-away” point for this is that you must commit to a move date. Once you’ve determined your end date, you make that your last row on the chart, and then the fun begins.

So armed with my blank-white 44 inches of paper, I outlined what I thought it would take to make the move. I started with what I knew, and wrote out goals to research the things I didn’t know. 


So at the end of my 44 inches, I wrote a vertical line that said “MOVE,” December 10, 2007.

Check that off. That helps, because it tells you where the end point is. And I knew the beginning point, so I drew a vertical line at the beginning of the 44” and wrote “START.” We had (I think) about 90 days to get everything done.

Then I summarized all the major events that would have to transpire along the way and place goal dates or “benchmarks” as I refer to them in rough estimate. Among these were:

1) Sell or rent our home (and get it ready- realtor, marketing, repairs, etc.)

2) Take care of the other rentals and commercial properties- skip this one if it doesn’t apply)

3) Take care of business obligations (for us it was our ownership steak, but for you it may be taking care of unfinished business with your job or relocation)

4) Pick a first tier “pack date,” which are the items you will pack and place into storage or ready for your container to ship to Hawaii. You must have all your other items sold or given away or stored locally (if you choose to keep them for some future date.”\

5) Pick a second-tier “pack date,” this is where you have your final stuff packed (clothes, immediate need things.) The second-tier “pack date” will be a day or two before you leave. At this point, you should be ready to go to the airport with your last items. We packed six boxes of stuff that we left at a friend’s house. He shipped those items to us when we had a permanent address (items that we needed fairly quickly, but not bad enough to take with us on the plane.)

6) Choosing a moving company for your house and/or office. You will need to put your items into storage or send it if you know where you’re moving (which Island.) We used West Pointe Moving, and our major items arrived in a 45 foot Matson container (more later.)

7) Research where you want to live. This could be big (if you don’t know which Island,) or smaller, if you’re being relocated or already know the Island, and even better, the community you’re wanting to relocate to (Kona vs. Hilo, Maui vs. the Big Island.)

8) Make plans for when you arrive. This could be as advanced as lining up a rental or home to purchase, or as little as picking hotels and rental cars to use during your first phase when you’ve landed in Hawaii. On a side note, we didn’t make any plans for when we landed. In fact, we didn’t even have hotel rooms or rental cars booked after we landed in Las Vegas during our move. (We love Las Vegas, and decided that we would spend a week there over Christmas to help break-up the trip. And even though it was Christmas, we were still able to find a hotel and rental car to start with upon landing in Maui. We didn’t even know which Island we wanted to live on while we were in Vegas, and it took one last trip to the Big Island before we made our decision. So if you already know your final destination, you’re in better shape than we were!

9) Family, Friends, and Business Associates. You’ll need to break the news to your close friends, family and business associates. This is a delicate area, so try to make a list of anyone you want to talk to.

10) Make a list of all the utility companies (phone, water, internet, etc) so that you can contact them to transfer the utilities once you find a tenant, or to the new owners, once your home sells. With the advent of the internet and cell phones, we weren’t too worried about this. 

11) Check your furnace filter and walk through your home before you leave. Make sure you have a list of maintenance companies lined-up and a contact to check on your home if you’re trying to rent it out or sell it.

12) We placed “Post-It Notes” on everything in our house that we wanted to sell vs. keep. Then we set a deadline to list everything on ebay or give to friends or family (items we didn’t need.)

There were many more items on our list, but the point is, brain storm everything you can think of and stick it in the right place as a “dead line date” on your chart, and work like hell to get it accomplished by that date. For example, I knew I had about 90 days to get rid of over half our stuff. So I started listing stuff immediately on ebay and kept listing everything until I completed my goals.

What To Bring With You

Everyone’s different, but here’s my take on what to bring:

If you’re moving to Hawaii, I can recommend to bring as little as possible, but bring the stuff you’ll definitely need. For example. We sold a beautiful sleigh bed cheap on ebay, just to figure out we needed a larger bed for our 9 year old. It wouldn’t have cost us anything extra to bring the nice bed, but to buy a new bed out here is very expensive. So bring the things you know you’ll need, but try to leave as much of the junk as possible.

We met a nice couple here shortly have we arrived. They had actually brought two 40 foot containers over and their entire garage was packed full of crap. The gentlemen told me he was frazzled, because he didn’t have any idea what he was going to do with all the stuff.

We love Hawaii so much, and here’s a tip: you’ll spend less time inside your home by a mile than when you lived in a colder climate. We spend most of our time (besides when we work at home) on our Lanai (outdoor balcony.) And we’re always walking, going to the beach, or visiting Kona, Hilo, Hawi, etc. And the big “take-away” from this is: Don’t bring a FRACTION of your clothes. I haven’t wore a pair of pants in the last six weeks (since I’ve lived here.) You don’t wear button-downs (unless you want to,) and you really don’t need 80 pairs of shoes or socks. The normal dress here is shorts, a t-shir, and flip flops. Seriously. That’s what everyone wears everyday. I could have tossed all my clothes and brought a handful of t’s and shorts and I’d have been fine. And my wife’s purse collection is still in the box it came in, and she hasn’t wore a dress or dress-shoes since she’s been here. So basically, we could have probably gotten rid of even another 50% of our stuff and gotten down to a 20 foot container instead of getting a 45 foot container.

We ended-up bringing our big-screen T.V., which will be obsolete soon, but we really don’t watch t.v. much here. We several nice t.v.’s we watch in our bedrooms before we go to sleep, and we’re glad we brought our stereos. We’re always playing tunes, and we love the local stations.

Cars: Bring or Sell and Buy When You Get Here?

Again, this is different for everyone, but we were happy with how we did this. First, if you have a vehicle that is paid-off or that is in good shape that you’re happy with, you may decide to bring it. Plan on shipping your car costing around $2,000. So you can do the math, but you have to weigh things in like the fact that if you’re happy with your car (you know how it runs, etc,) you ‘ll have a slight risk by buying a new one. Second, you may not be able to sell your car for what you want, so that could impact the numbers. Third, can you wait three or four weeks for your car to arrive?

What we did is ship one of the cars and sell the other. We parked both cars at a friends house, waited to find out where we wanted to live, and then had our shipping company bring the one car. I placed the other on ebay and sold it last week. It worked out really well for us. We bought a car in Hilo (at Big Island Used Cars,) and were very happy with our purchase. We bought a Chrysler convertible, so I love driving the convertible in the sun. My wife had her SUV shipped, and she was so excited when it got here.

Regarding all the items on our action plan, my wife and I spearheaded different parts to this project and reported back to each other throughout the day. We felt we started making headway when we first narrowed down our decision where to live. It was either Maui or the Big Island. Also, once we decided on either Maui or the Big Island, I started researching everything possible about these islands. But don’t get overwhelmed. No matter how much you research, there’s no substitute for getting here and driving around seeing the places in person.

Contacts To Make

Here are a few of the contacts that we made that really helped.

1) Rental Brokers. We knew we’d probably rent prior to buying here to make sure we liked the area.

2) Business Brokers. If you’re looking to purchase a business, you may want to try to find a decent business broker. I had a couple REALLY bad experiences with brokers here. More on that later.

3) Realtors. We made a ton of contacts with realtors, even though we knew we probably wouldn’t buy right away. It’s hard to find a good realtor, so we started early (more on this later.)

We shifted our auto insurance to Geico (our Indiana insurance didn’t transfer,) and we’re in the process for shopping new help-care.

As time ticked-on, we started crossing things off our list. The next step is when things hit “hyper-drive,” so get ready. It’s also a very exciting time, especially since we were leaving Indy when the weather was turning very cold. Next part: “Pre-Leave.”

Planning Your Move To Hawaii

”Pre Leave” On Your Move To Hawaii

Travel Before Your Move To Hawaii

Setting Up Shop On Move To Hawaii

Community And Your Move To Hawaii

Getting Your Stuff After Your Move To Hawaii

Best Practices For Move To Hawaii

Mistakes To Avoid During Your Move To Hawaii

Frequently Asked Questions About Living In Hawaii

Copyright 2012 Chris Anderson Hawaii Trip Report

Site Map

How To Start A Business

Free Sales Training

Vinyl Banners and Hawaiian Trade Show Displays

Hawaii Car and Truck Wraps / Graphcis

coolest guy in hawaii

Hawaii Elementary Fundraising Ideas

Hawaiian Candle Fundraising