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| My Children Were Fascinated by Waves on this Black Sand Beach |
In 2005, my wife, two children, and I went to Hawaii. My wife was going on business; the rest of us tagged along. This was my first trip to Hawaii, and if we were going that far, I wanted to make it count. I had no idea if we would ever go back. My wife’s business took her to Kauai, specifically Poipu, so we started there.
While my wife was busy with work on Kauai, I took my children and explored the island. My wife joined us for some of these drives when she was able. We visited the Waimea Canyon, and lots of waterfalls, and lots of beaches. My daughter and I hiked some of the Na Pali Coast.
Then we flew to Hawaii and stayed in Kailua on the Kona Coast. We explored a lot. We went to Punalu’u black sand beach, and Hawaii Volcanoes National Park, Hilo, the Waipio and Pololu lookouts, and lots of beaches. We saw lava fields and volcanoes and sunsets.
My wife and I started talking about how cool it would be to retire in Hawaii.
We made several more vacation trips to the islands, to Oahu, and Maui, and we returned to Kauai and Hawaii. We explored and checked neighborhoods. We shopped at Target and Walmart and Safeway. We saw waterfalls and sandy beaches and rocky beaches. We saw mountains and flowing lava. We saw turtles and goats and mongoose. And chickens. Lots of chickens. And we kept saying, we could live here.
Twenty years later… In 2025, I was getting really tired of working. My wife had retired from full-time work and was doing consulting. Our children had left the home. Our retirement investments had done well. I said to my wife, let’s go to Hawaii and Maui next year and really explore neighborhoods and target a 2027 move. Let’s really think hard about whether we’re able to afford it there, and let’s ask ourselves, is that really the lifestyle we want in retirement.
The safest, most financially responsible thing for us to do is stay put in Virginia. We have no mortgage or car payment. We’re established with doctors and a dentist. We’re settled, and comfortable.
But we’re not doing the financially responsible thing. We’re contemplating selling our house and moving to a much more expensive location. We want to live in a place that brings us joy; Virginia is not that place. It was a great place to raise our family and have careers. That no longer matters.
Well we made the exploration trip in October 2026, our 8th trip overall, 5th to Hawaii, 3rd to Maui.
It didn’t start well. We had to scramble to get there a day early because a hurricane was looming south of Hawaii. We feared we would get to San Francisco and be ready to board our flight to Hawaii only to have the flight cancelled. But we got there and explored the island again, even having to turn back in driving rain at South Point (hurricane rain and wind). My wife was having serious doubts about moving. We found some good neighborhoods with good houses, but concerns about volcanic eruptions and access to medical care started to creep in. The places we liked were a long way from grocery stores. It was obvious to me that my wife was very reluctant to move there. Then she broke a bone in her foot. We went to a clinic for treatment, and they sent us elsewhere for X-Rays. The X-Ray clinic closed at 2PM; we just missed it. We could have just gone to the emergency room at the hospital nearby, but she chose to wait for the X-Ray clinic to open the next day. She got crutches and a boot at the clinic. She was really dissatisfied with the whole experience. We both know it’s unfair to judge the medical services based upon that experience alone, but it’s hard to look past it.
I was concluding that we would end up changing our plans, that we would settle somewhere else, someplace on the mainland.
But we had another week planned on Maui, so we flew there. Immediately upon landing she had a follow-up appointment with an orthopedist. That went well and we took the opportunity to explore Upcountry near the doctor’s office. She was much more satisfied with that medical experience than that on Hawaii. Of course it’s unfair to judge based upon that single event.
We checked into our lodging in Kahana and started exploring. Before our trip, she had spent some time watching YouTube videos posted by a real estate agent on Maui. My wife totally surprised me by contacting that agent and setting up some home visits. I thought this was very premature; we weren’t going to move for at least a year, but we went on a tour of houses anyway. We saw 12 houses over 2 days. My wife was suddenly talking about researching the history of the house that we most liked. She was talking about the prospect of selling our house to buy that one on Maui. She researched the process of shipping cars and household goods to Maui.
Over the course of just a few days she had gone from really reluctant to move to Hawaii to all-in on a much shortened timeline for a move to Maui.
So now we’re back home and working on getting answers to some lingering questions before we make an offer on our preferred house. We’re taking our time, knowing that someone else might buy the house in the meantime. But we think that’s unlikely because it’s overpriced.
