How To Winter in Hawaii – With Kids, Without Money

June 27, 2010

Our two munchkins last winter in Hawaii

Yes, we’re doing it again. 3 months this time!

I posted to Facebook that we were spending the winter in Hawaii again, and got this comment:

I love the minimalist approach. But how does one deal with the high cost of travel to Hawaii? Honolulu is also very expensive, right? how do you deal with that when you have kids? Can you please share this? It will be useful for people like me who would love to do this!

Here’s my reply – the top 10 tips for how we spend the winter in Hawaii, with kids, without breaking the bank:

1. Be frugal. We live well below budget while we’re in California, so we save up money for the flights. It takes discipline, but the freedom is worth it.

2. Pay one rent. We rent a small apartment (1 br) on both sides, giving up the lease when we move so we’re never paying double rent – and rent in Honolulu is about the same as in Silicon Valley, so our living expenses are actually about the same.

3. Find cost tradeoffs. The one thing that’s much more expensive in Hawaii is food, but that’s compensated for by the fact that life is so much simpler there – here we pay for kids’ activities, entertainment, transportation etc, while there you just walk to the beach every day for free fun that never gets boring for the kids (or the adults).

4. Hang loose. When we’re in Hawaii, we don’t pay for all the over-priced touristy stuff, but instead live more like locals.

5. Find work that’s portable. We focus on building up work/revenue while we’re in California that is compatible with extended time away – things that we can work on remotely for now, with the goal of moving towards increasingly passive income.

6. Pounce on sales. We keep an eye on flight prices, scooping up deep discount sales that are often available months in advance of when we leave.

7. Self-store your stuff. We store our California belongings in a small self-storage place while we’re gone (we don’t own anything that doesn’t fit in our car, so moving costs are negligible), and we rent a furnished place in Hawaii. Also, each time we put our stuff in storage, it’s a great excuse to give away the inevitable accumulation of things that happens over 9 months, so we stay super lean.

8. Use your feet. We choose places to live on both sides where you can walk almost anywhere, and bus/train if you need to, so while we’re in Hawaii we don’t have a car (and we’re thinking of giving up our car in California too, actually)

9. Be curious. We expect hiccups on either side, but it’s all part of the adventure – we also homeschool our kids, so there aren’t any ties to school schedules, and they get to experience with us how a person goes about finding shelter, food, and community in a new place. Important life skills!

10. It’s ok to be different. I say if you want to do something, just do it, and the world around you will move to accommodate you. People feel sorry for us that we live in a 1 br apartment with 2 kids, but we feel like it’s the greatest thing in the world – we’re all so connected, and we get to live wherever we want!

I hope that answers the question and inspires whoever is reading this to live life your way.

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3 Responses to “How To Winter in Hawaii – With Kids, Without Money”

  1. Alexandra Says:

    Two things I should add:
    Be Super Productive! I find that the relaxation and lack of distractions in Hawaii gives me the space to be both more creative and even more productive. You will need to show your employers/investors that you are more effective while you’re away, to compensate for the lack of face time.

    Timing. We haven’t yet experimented with how long we can be away without breaking our social support structure, but fortunately we are not incredibly social people to begin with, and online tools make staying connected easier. Still, making time for face-to-face interactions to rebuild bonds is incredibly important when you get back.


  2. […] 3. Live Simply. Or, get rid of all the useless stuff in your life. I live with as few things and commitments as I possibly can, and I highly recommend it! It feels wonderful to shed the heaviness and just be light. I recently wrote about our simple lifestyle here and here. […]

  3. Mara Hagen Says:

    Thank you Alexandra!
    you have always inspired me…I love your courage& sense of adventure in life!


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