No one wants to talk about LEAVING HAWAII…but at some point we all should or must leave…may it be for vacation, a trip back home, for work, or unfortunately because we can no longer make ends meet in Hawaii. Even those BORN & RAISED sometimes leave Hawaii because they are going off to school or can’t make ends meet anymore in Paradise. It happens…it happens to the best of us and at some point we need to all face it for one reason or another.

We’ll be the first to let everyone know…Leaving Hawaii is a hard thing to do and there are many reasons why someone would leave…No matter the reason…leaving Hawaii is NEVER EASY…but we’ll be the first to also tell you…returning to Hawaii ALWAYS IS!

10 thoughts on “LEAVING HAWAII

  1. the only reason i noticed the L/R issue was because i listen at work and leave one earbud out so my annoying coworkers can’t sneak up behind me.

    so regarding the mileage tax…

    “which would potentially replace the fuel tax”

    HAHAHAHAHA!! yeah. potentially eh? this is going to end up “oh well we need to keep the fuel surcharge going to fund the administration ($19 million!!!!) first few years of the mileage tax…” and then once the mileage tax is up, running and profitable they WON’T do away with the fuel tax.

    congrats on the new place brucie! post up some pics on the old facebook when you close. and yes, if you do a solo podcast i’ll be here listening while wayde’s freezing his dingus off in the icy northeast!

  2. Hi Bruce and Wayde,

    I have been listening to your podcast for a few weeks now and am really thankful for the great advise and laughs I’m getting out of it on my way to and from work. My girlfriend and I working towards our goal of moving to Oahu from California next September/October and this podcast is really insightful. We have been to Kauai twice and got bit by the Aloha Spirit. Our initial plan was to move to Kauai but after listening to your podcast and doing more research we decided it would be easier to start out in Oahu. So we will visit the island for the first time in February. We are super excited and already booked a small rental property on the North Shore, from where we will explore the whole island to get a feel for all the different areas.
    I have to admit I didn’t listen to all your episode yet, but if you haven’t yet, I was wondering if you could touch on the topic of living in Hawaii, specifically Oahu with pets. We have a small border collie/spaniel mix (22 lbs) that we will bring with us when we move and looking at rental properties on craigslist and other websites it seems very hard to find places that accept pets. I saw that Wayde and his team did a lot of volunteer work with local shelters bringing shelter dogs on hikes with them and I love them for that. So yeah an episode on living with pets, maybe even about bringing pets to the islands (even though I did a lot of research on that topic already) would be great! Pet friendly activities, pet friendly rentals etc.

    I’m also wondering if Bruce could share more information about the condos he is renting out. We will need a temporary place to stay when coming to Oahu next September and renting from him would be great. I promise we won’t trash the place and do our dishes 😉

    Thanks so much for all the great work you do!


  3. Sebastian – you may want to check out a website and ebook on moving to Hawaii. She breaks down everything you need to know/do when it comes to moving to Hawaii with pets in painstaking detail with timelines. We have a dog and found this info very helpful as we plan our own move:

    • Hey Matt,

      Thanks so much for your reply.
      I think I know which blog you are talking about and have it already bookmarked. I think I got all the information I need for a direct release at the airport. Now I just have to hope we don’t make a mistake with all the paperwork required.

      What concerns me the most is finding rentals that allow dogs. While I found a few apartment buildings that allow pets, it seems to be very hard to find a house/guest house or duplex to rent with a dog.
      Did you look into that at all yet?
      I’m sure it’s doable. It just lowers the already scarce options out there.


      • I have talked to a couple of property managers and they’ll often advertise homes as not accepting pets even if the owner might be open to it conditionally. I would say cast a wide net on the kind of places you’re interested in with respect to rentals, let them get to know you, and then bring up the subject of pets/introduce your dog. I think there are a lot of owners who, while they might ideally look for tenants without pets, prioritize other factors like employment, credit history, rental history, etc. in reviewing a prospective tenant. That was definitely the case with us when we rented out the place we own in HI. It probably means a little more leg work in reaching out to more property managers/owners, but it may be worth it since it sounds like you really want to be in a house/guest house over an apartment. I hope you guys are able find the right spot for you!

  4. Gentlemen:

    Your podcast is something I look forward to whenever a new one is released. The information is really helpful, and your honesty and frankness is what keeps me coming back.

    I booked the Aloha Plate Tour, a helicopter ride and car rental through Hawaii Aloha Travel. Abby set up everything and she was great to deal with. Bruce, thank you for the podcast listener discount.

    My wife and I are in Oahu now and staying until October 17. We have not visited for 3 years and man have things changed. Everything in Waikiki is way more expensive, even a lot of the hole in the wall hotels and restaurants are charging big bucks. Although expensive and full of chains, the new International Marketplace is great. Roy’s Eating House 1849 has amazing service and the food is on point.

    The two of you make a great podcast, thank you.

  5. Every time I have had to leave Hawaii has been painful — gut-wrenchingly painful — because as a visitor I haven’t known when I will be returning. The first time I stepped off the plane in Kauai with my wife on our honeymoon it hit me immediately, like the powerful feeling of love at first sight or an instant attraction, and I still get that same electric feeling after many trips to Kauai. We’re looking to move our family there next summer (we already own a house there that we rent out now) and would appreciate your perspective on the neighbor islands and people who have successfully transitioned to them. We still have so many questions but want to make this move because we love Kauai deeply and want to get engaged in the community and find ways to contribute. Like the stories I’ve heard from your guests, there’s a lot behind our desire to be there, as hard as we know some of the challenges will be (transitioning young kids, careers, and a dog). Thanks for bringing us so many guests who have told about their struggles to make a move work – it’s a huge help to anyone thinking about, or committed to, a move to Hawaii.

  6. Hey guys! I know you’re on hiatus, but just wanted to tell you that we secured a house in Wailuku for the same price & size as we’re renting now in Pasadena! Lucked out and got connected with a great realtor named Sherry Tuttle with Elite Pacific Realty.

    This has been a crazy ride and we’re almost there! Mahalo Nui Loa for all of the support and words of encouragement. We’ve done this whole move on a shoestring budget, but with a genius plan that’s already reaping rewards.

    As always keep up the great work, and as soon as we get settled, We’ll hop over there and meet up with you guys.

    All the best

    Rico & Mayra

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