Our Move to Hawaii


After seven years of hard work, and about six months of preparation for the move, our family of seven arrived this past week in Hawaii to start the next chapter of life. The journey has been exhausting, stressful, sad, exciting, liberating and incredibly worth it. In this post I’m going to share with you a bit more about what life has been like leading up to our flight out here, and since we’ve arrived.

Saying goodbye

It was hard on the entire family saying goodbye to our friends and family. We had been living in Portland for the past 7 1/2 years. Good friendships had been formed, we had great neighbors, a great church, a great cat, and we had to say goodbye to them all. In the midst of all the goodbyes there were two things that helped make it easier. First were the assurances from many friends and family members that visits to us would happen in the near future. That is one of the benefits of moving to a tropical location. Everyone wants to come visit. The second, was that we decided to ship our cat Wilson out later this year. Some very sweet friends of ours volunteered to watch our cat and help us get all the paperwork, shots etc in order for him to come out. It was exceptionally hard on us saying goodbye to him. It’s like leaving a member of your family behind, but to make it worse, you can’t explain to him what’s going on or that we will see him again.

Our life in our luggage

We arrived at the airport with a small mountain of luggage. 12 checked luggages and 12 carry on items was all we brought with us. We stored a few items back at our home in Portland, but the rest of our things we sold. It was very draining process having to decide what to do with every single item we owned. Do we sell it, store it, ship it or give it away, times thousands of items. We ended up bringing mostly clothes, kitchen items, tools, appliance parts and office items.  Though it was hard, the process was also very liberating.  It’s always a surprise how little we can actually get by with and quickly forget the things we gave away or sold.

It took three vehicles just to move our luggage to and from the airport and to transport our family. If I had any regrets it would be not being able to get all of our stuff in 10 luggages, reserving the final two luggages for all our carry ons. The most difficult part of our travel was getting our carry on bags inside the plane and into the compartments. But, all bags over 12 we would have started to pay $100 per bag so the inconvenience saved us at least a few hundred bucks.

All said, I think we did well shrinking our belongings down.

Life without a car

When we arrived, our friends picked us up(again with 3 vehicles) and dropped us at our house in the middle of the town we moved to. In spite of combing Craigslist for the past few months, I hadn’t been able to find the right car to purchase before we arrived. So we had no car and it actually felt quite good for a couple of reasons.

First, living right in the middle of town we could walk to everything, and we did. There is a grocery store that is about a 3 minute walk, convenient store about 30 seconds away, restaurants 3-5 minutes away and even our church is within a few minute walk. We walked this past week more than we have in the past 6 months, and the exercise felt incredible. The kids loved the extra hang out time and walking everywhere has a tendency to slow life down a good bit.

Another reason it felt so good to not have a car was that cars are expensive. Insurance, registration, local vehicle emissions certificates, gas and vehicle maintenance. Plus out here in Hawaii cars literally rust away.

But, even with these bonuses, we ended up buying a vehicle a few days ago. No car made it very difficult to make it down to the beach as a family, getting to and from friend’s houses that do not live immediately in town, the ability to shop at larger stores that are about 30 minutes away etc. Even just setting up life, buying used things on Craigslist, and work/business are all difficult to pull off without the ability to drive around.

Getting settled in the tropics

Life has been good since we arrived. I’ve been able to go surfing four times already which has been incredible. Surfing provides exercise, exposure to the sun, time with friends and one of the biggest benefits is that it’s a great stress reliever. When you are out in the ocean, it’s hard to focus on anything but the oncoming waves. Surfing is a beautiful thing.

Our kids have been chasing geckos and all sorts of other insects pretty much non-stop since we arrived. They seem to be back in their element wearing slippahs (flip flops) and board shorts all day every day.

Adjusting to the high food prices is a bit of a challenge, especially when we’re feeding 7 people. But my wife has been adjusting well by taking advantage of the local farmers markets, changing the menu a good bit, picking fruit from our backyard as well as ordering much of our food in bulk from a few different island sources.

We’ve really enjoyed being able to spend a lot of time reconnecting with our friends out here since we arrived. Having a community of friends already here has definitely made the move and transition much much easier.

Onward from here

In the coming weeks I will be writing more about starting to work again and the process of figuring out what business is going to look like here. It’s definitely different, and I’m already seeing that I’m going to have to be flexible while I’m getting things going again. I haven’t been in a huge rush to jump back into full time work mostly because we are still recovering from the months of hard work and preparation to get out here.

I apologize for not writing more during this time, but life has been very full. I hope you all are doing well. Aloha from Hawaii


  1. Aloha Ryan! Congrats on the move. My wife and I just got back from the Big Island ourselves, and I’m with you, there’s something magical about “living on a rock in the middle of the ocean,” as one person we met explained it.

    Looking forward to following along with this next chapter. Cheers!

  2. Ryan Finlay, a great lad you are and so resourceful!!
    You should be proud of yourself!
    Onward and upward.
    I am a wee bit jealous of ye by the beach. I love the beach 🙂

  3. Man! Such a good read!

    We are putting our house on the market with the thought that we will spend a few months traveling the country and/or settling in Florida.

    We thought of checking out the Island or at least the west coast, but we worried that the high prices might make those areas less fun for us in the long run.

    Eventually, we’ll be right back here in the midwest and either build or buy ourselves a new place.

    So it’s good to hear stories of other adventurers.

    I presume you will still be Re-Craigslisting over there?

  4. I admire your courage in leaving friends, church, familiarity, your cat, starting over, the expense. I hope you will be exceedingly happy. May your funds stretch greatly. I imagine a family of 7 is accustomed to managing well and I’m sure you’ll do fine. If nothing else, I feel sure you will feel more secure geographically. Many are leaving the USA and I’m one that is considering it seriously. I feel sure it will be a safer place for your family. Blessings!

  5. Glad to hear you’re adjusting over there! I imagine the whole move was an intense process but fortunately the worst is over. I admire you deciding (with your wife I’m sure) that such a massive change would reap benefits. Change can be extremely hard sometimes, but props to you for powering through. I myself have been busier than ever with school but I’m so close to finishing that I literally can’t wait to get out. In the meantime I’m still tinkering around online buying/selling.

    On that note, I’ll be ready for some new stories of your reborn business on the Big Island! I have no doubt that you’ll have fun!

    PS. Do you ever shop at Costco for certain things? I’m curious because I usually hear from larger families that it saves them considerable $.

    • Thanks Aleks, will keep the stories coming, they will be interesting!

      We definitely are shopping from Costco out here as it saves a lot money. Also ordering things on Amazon and having them shipped out with free shipping saves a lot of money.

      Congrats on almost being done with school, that will feel great!


  6. Hi Ryan, We are really happy for you and your family! As you know, we moved from the Seattle area, out to Florida just under a year ago. You will have many visitors – so don’t be sad about leaving Portland. All the people you care about will come visit and vice versa. You’re going to love your new life in the sun! God’s blessings on you and your family! Tom & Christy

  7. Hi Ryan. My husband and I are moving over to the Big Island with our 3 kids in August. We have started paperwork for 3 dogs and are still trying to figure out shipping some items. Is it really cheaper to just sell everything and re-start? Other then each bringing a few suitcases of clothes. I’ve been looking at so many different articles my brain is just overwhelmed. Shipping postal service vs. shipping on a palat vs shipping in pod ETC ETC.

    • Hi Tara, I would make a list of items you think you really want to ship over here and then wrestle with how much it would cost to replace them here. One of the best deals for shipping things over here is actually via the airline when you fly. You can ship large plastic totes filled with 50 lbs of stuff and each flyer gets two bags each for relatively expensive (at least with Hawaiian Airlines)

      For the amount it costs to get a container, or even small container, you can buy the items new over here and start over. I would sell big items like beds etc back on the mainland. If you want, I can put you in touch with my wife if you would like to bounce some ideas off of her. Shoot me an email at ryan@recraigslist.com if you have any other questions! That’s exciting you guys are moving over! Which side of the island will you be moving to?


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