I received this email about someone considering moving to Oahu recently and I reply below.

Hi Vern,

I just finished your book about living in Hawaii – I thought it was a good resource, and you mentioned you welcomed emails – so I wanted to ask you a question.

I am an entrepreneur and I can work with my clients remotely. I’m coming from a big city in a foreign country, and high prices won’t be a surprise for me – though I like to keep my expenses low whenever possible.

I have never actually been to Hawaii – so I am planning a trip to check it out June 24 to July 2 to decide if I want to really do this. If I go through with the move, I would probably do it in September or sometime before 2014.

So my question is this: for someone making a preliminary trip to decide like this, what would you recommend doing and seeing?

As mentioned earlier, I like to keep expenses down when possible. For place to stay, I was leaning towards an apartment listed on Craigslist instead of a hotel (seems like I could do $70/night all in with a kitchen, vs $120/night for comparable hotels?). For car rental – do you think I need one for the full week? I haven’t had a car in 8 years, and I’ve grown to love the lack of expense as well as responsibility.

A friend of mine that used to live in Hawaii highly recommended Kailua. I’m single and pretty laid back. Commuting isn’t an issue since I can work from home – though I might like to consider working in a shared office setting for the social aspect (and change of scenery from home).

I definitely plan on seeing Kailua during this trip (maybe staying there), but I was wondering – for someone totally new to Hawaii – what else would you recommend doing during a trip like this, while deciding on the move? Should I do an organized tour of the island to give me an overview of Oahu? I plan on checking out places like Costco and Safeway to understand prices, any other things?

I’m very adaptable, but think living in Oahu will be good for my first year since it has the most people and things to do. Do you think I should stay in Kailua or Waikiki or somewhere else during this trip?

Any advice/tips for this trip or any other thoughts on things I mentioned would be greatly appreciated.

Best regards,

* * *

Hi Max,

I thought this was a great email because of the questions asked. I don’t remember replying to this same question, or writing an article about it, so I wanted to bang this out quickly if I could.

If you’re flexible about where you’d live, I definitely recommend living on Oahu first. Waikiki in particular since you won’t necessarily need a car if you’re working from your apartment. Waikiki has a lot of activities close together. You can walk to food shop, clothes shop, surf, climb Diamond Head Volcano, and to the nightlife. Kailua is a great place to live, amazing really, but it’s more of a family location, or for someone with heaps of money that doesn’t mind running across the mountain to get into Waikiki and the activities there. Kailua has few places to really stay, Waikiki is probably going to be your best choice.

If I had a limited time to go and check out the island I would have a car for at least 5 days I think. I would circumnavigate the island and see all sides of Oahu. I’d see the whole thing because every part of it is different. Different beaches, different feel, different geographical features. Different pace really. See if there is enough to keep you happy for a couple years, or however long you see yourself staying.

You’ll want to spend some time at the major beaches – Kailua; North Shore; Waikiki; Diamond Head if you surf; Ala Moana; Sandy’s; Bellows AFB or Waimanalo. You’ll want to check out the major shopping spots – malls mostly. Check prices to other islands, you will likely want to be able to visit some when you come to live. Gather heaps of brochures to take back with you. Don’t forget Hanauma Bay and Makapu’u beaches. Like I almost just did.

Talk to as many local people as you possibly can. Figure out what it would be like to live on-island. Ask what they pay for groceries and eating out. Figure out where some of the weekend produce markets are for fresh fruits/veggies at reasonable prices.

I’d check out Walmart, Target, and any other big store you can find just to see if there’s anything you are used to seeing that isn’t found at any of the stores on Oahu. Food choices are going to be limited, hopefully you’re adaptable in that area as well.

If you find Oahu overwhelming, you might want to try Maui or Big Island for a day to see if one of them might be more your style.

Hope that helps. I would love to hear how you make out on your visit and if you decide to move to Waikiki, or where.

Best of luck to you!


Peter Kay