Island Bound 1: Dreams of Maui

A couple of years ago, my wife, Sarah, and I took a vacation on Maui. Sarah had never been to Hawai'i before, so I was curious to see how she liked the place. I used to live on Oahu many years ago, enticed out to the University of Hawai'i at Mānoa from Denver when my future boss said something like “well, you’ll have to spend about half your time in the water training dolphins.”

Sarah lived for a while in Costa Rica, and had thoughts of returning to that sort of climate at some point. Sitting at a table in Ka'anapali, sipping a cold drink, looking out over the ocean, Sarah commented “this is so much like Costa Rica, but something’s different.” I'm a pretty experienced traveler, but it's one thing to visit a foreign country and quite another to consider when buying real estate, settling down and such. Also, Costa Rica is a long way from the west coast. I responded “It’s in the U.S.” and her reaction was “Whoa! Yeah, that’s it!”

I think our dream of moving to Maui may have started at that moment.

Over the next couple of years, we returned to Maui a few times, staying in different locations to try out the many microclimates and communities found on the island. We did the resort thing in Ka'anapali. We stayed in a cottage by the beach in Kihei, and in an ohana in Pukalani. We explored the south shore down to Makena and the north shore down to Haiku. We started gravitating to the upcountry area (is that antigravity?), and fell in love with the vibe, and the views, in Kula. I reached out to an old acquaintance, a realtor on the island, and started the process of getting more serious about a future with the word “relocation” in it. 

House hunting on Maui can be exciting and frustrating. Houses can be ramshackle but crazy expensive, neighborhoods can change dramatically by turning a corner. As a mainlander, you need to understand the difference between lease hold and fee simple. New home construction is surprisingly costly per square foot - and many neighborhoods dictate a minimum size enclosed space - lanais don’t count. There are garden views, and territorial views, and ocean views - and something I’ve only heard of on Maui, the bi-coastal view, where you look sort of westward at the West Maui Mountains, and you’re able to see both north and south coasts. And there’s the concept of the Condominium Property Regime

Early in 2013, house-hunting, we fell a bit in love with a little place just up the road from the Kula Lodge. Not quite a bi-coastal view, but a sweet view of the north shore, Kahului, the West Maui Mountains, and even Moloka’i in the distance. We arranged pre-approval with a local lender, and thought long and hard about making the leap. In the end, however, we decided the time wasn’t right, and we left the island for home.

The story doesn’t end there, however...

[next: Island Bound 2: Timing is Everything]