A reader writes:

I’ve read many of your posts and links about military retirement in Hawaii. It’s not something we had considered previously, but it sounds pretty good. Apart from the high cost of real estate, what are the pitfalls? We are a pretty frugal couple, so I don’t think the excise tax would be too bad for us. My spouse is retiring from active duty this year, and we are both “beach people” with a fair amount of experience living and traveling overseas. We’re not surfers – we both scuba dive.

(We found your blog from MrMoneyMustache. Thanks for serving the military community in this way.)

You’re welcome, and thanks for inverting the question! This is the first time I’ve focused on reasons NOT to move to Hawaii.

Kamehameha Day lei draping ceremony
Photo courtesy of my daughter

Part of the challenge of answering this question is that people place different priorities on different factors. I grew up in Pittsburgh yet I’ve never waxed nostalgic about experiencing all four seasons (let alone winter) or being able to drive hundreds of miles in a straight line. However, those are two very common reasons that servicemembers didn’t enjoy their Hawaii tours.

Whether you’re commuting to work, or self-employed from home, or even if you’ve earned your financial independence, here are some other issues.

Oahu is a 600-square-mile island. Its “small” size can drive many people nuts. Yet in 23 years we haven’t explored even half of it, and we have not yet visited Lanai or Molokai. We enjoy returning to our favorite spots again and again, and occasionally we’ll try something new. I’ve spent most of my decade of surfing at the same break, only tackling other breaks when they’re big.

I think the biggest pitfall of living in Hawaii is proximity to family. If you have Mainland relatives who you’re close to, or aging parents who need your help, then you’re going to get awfully tired of the 2500-mile five-hour flight between Honolulu and the west coast. People on the Mainland claim that they’re going to visit, and they do it once or twice, but the plane fare is discouraging. After the first couple trips you’ll spend years swapping Facebook updates before you get together again.

Local kids are likely to leave Hawaii for a Mainland college, and then they’ll start a Mainland career. They’ll meet someone on the Mainland, you’ll enjoy their Mainland wedding, and someday there’ll be Mainland grandkids to visit. It tends to draw your interests back to the Mainland, and we see it a lot among veterans. One of our local submariners retired from active duty in the 1970s and started a real estate agency. He hired dozens of veterans who were stationed in Hawaii and wanted to stay here. But one by one, during the next decade or two, they all relocated to the Mainland– closer to aging parents and new grandkids.

Excise tax is not much of an issue alongside commissaries, exchanges, and base gas stations. Costco, Wal-Mart, Home Depot, and Target are competitive with military shopping– even including the excise tax. Shipping expenses from the Mainland are still annoyingly high for online purchases, but there are ways to work around that. Eating local cuisine is fairly cheap, while Mainland food can be expensive.

Speaking of four seasons & driving, it’s best to live here for several months. The year’s “worst” weather is August-October (dry & “hot”) and January-February (rain & “cold”). House sit or rent an apartment. Use local transportation or buy a cheap sedan from a military base’s used-car lot. Live as local as you can… and then see if any of those pitfalls matter to you!

Related articles:
Lifestyles in military retirement: Living in Hawaii
Lifestyles in military retirement: Hawaii long-term travel
So You Want to Live in Hawaii (a very popular book)
How to Live in Hawaii (a very detailed blog about moving to Hawaii)
Lifestyles in military retirement: Napili Bay, Maui
Lifestyles in military retirement: Haleakala Crater, Maui
Lifestyles in military retirement: Haleakala Crater again
Lifestyles in military retirement: Learning to surf
Waikiki beach camera
HawaiiThreads discussion board (Register and then browse the “Islands Ahoy” forum)
Star-Advertiser newspaper website (Worth paying for a subscription)
Honolulu Civil Beat (another excellent online newspaper)