Lifestyles in early retirement: Hawaii long-term travel



Last week’s post on long-term retirement travel talked about different air & lodging resources for seeing the world. I’ve also added several military websites to the sidebar “Travel links” section. Like blogger Jan suggested a couple of weeks ago, it’s a great area for showing advertising from military lodging & recreation centers. I’d much rather have those advertising dollars for military charities than from payday loan companies.

Waianae sunset over Pearl Harbor

But for today’s post, a reader has a different slant on military travel:

My wife and I would like to be able to spend a month or two a year in Hawaii as well, to get a dose of sunshine! We’ll see how it all works out. Any advice for a couple of military retirees on how to live frugally in Hawaii for a couple of months per year? Working or volunteering somewhere in return for cheap housing?

Great question, thanks! My advice comes from these basics: cheap airfare, traveling light, finding long-term lodging, and living like a local.



My first advice on travel to the islands would be Space A. Your flight might land on the reef runway next to Honolulu International Airport, but you’ll end up on Oahu’s Joint Base Pearl Harbor Hickam. It’s possible (but unlikely) that a Navy P-3 might make the flight from the Mainland to land at Marine Corps Base Hawaii near Kaneohe. (Unless you’re a Navy aviator with deep contacts in the maritime surveillance community, I wouldn’t count on this option.) Those are your only military choices for getting to Hawaii, and you’ll have to transfer to a commercial airline (or a boat!) to get to the neighbor islands.

If you’re staying in Hawaii for a few months, and if you’re flexible on your travel dates, then you may be able to take advantage of airline pricing. In general, Hawaii flights are more expensive in the summer months when kids are out of school. June and July are also particularly busy for honeymoon travel. However, the most expensive flights to Hawaii are during the winter. The colder it is on the Mainland, the more the airlines charge you to come here. Late November through mid-February is “high season” for travel and lodging, so you’ll find more bargains if you can get here in September-October and leave in March-April.

If you don’t have to arrive on a particular date, and if you’re traveling light (no checked luggage), then be open to the possibility of getting bumped. Flights from Los Angeles and San Francisco are particularly good candidates for this option. You may spend several extra hours (or even overnight) at the airport, but you may be able to negotiate hotel/food vouchers and discounts on your next trip.


Houses, condos, cabins, and camping

Last week’s post talked about military lodging, and the “Travel links” sidebar has over a dozen links to military lodging & vacation websites. If you’re planning to live here for longer, though, I’m going to recommend other options. The advantage of these short-term military lodging options is that you have a starting point for checking out neighborhoods and rental ads before you make a longer-term choice.

The cheapest Hawaii choices are house swapping and house sitting. Of course this is challenging if you’re traveling with four kids, but older singles (and couples) are generally regarded as good candidates. My spouse and I have never done a house-sitting gig or swapped houses, so I’m going to defer to Sydney Lagier’s considerable experience and Billy & Akaisha Kaderli’s network with links that I’ve read on their websites. The largest and most popular house sitting and swapping sites are House Carers, Trusted Housesitters, Caretaker Gazette, and Home Exchange. (Of course for Home Exchange you actually have to have a home that someone from Hawaii would like to visit, too.) You’ll want to do your due diligence on these sites to learn the rules and the challenges of getting a Hawaii home. I doubt that you’ll be sitting in Kahala or Waikiki, but you could certainly end up elsewhere on Oahu or in a more rural location on a neighbor island. Make sure you understand your transportation options, too– the homeowner might not mind you sleeping in “their” bed but they could draw the line at driving their car. Bus service is available on Oahu, especially in Honolulu and other major neighbor-island towns, but as you get further away from the urban areas you’re going to want to borrow or rent your transportation.

Hawaii has a large snowbird population, and many of them are condo owners trying to rent out their places during the rest of the year. If you’re able to work around the snowbird months, or if you can find a snowbird who’s not visiting Hawaii that year, then you’ll be able to get a discount rental. We’ve seen the best success with Vacation Rentals by Owner and AirBnB. A third option is the military Automated Housing Referral Network, although this is mostly seeking military tenants for long-term rental properties near military bases. (We’ve used AHRN several times to find tenants for our rental property.) AHRN landlords would probably prefer at least a six-month lease but some of them will go month-to-month for Reservists or temporary duty personnel. Craigslist might also work if you know the neighborhoods and are willing to deal with the occasional eccentric landlord or a scammer.

Another option is lodging at military recreation areas, state campsites, and national parks. (See a few paragraphs further down for working at a national park.) You’ll be in “rustic” cabins or tent camping, and the length of your stay may be limited by high demand or agency policies. You’ll also need to carefully consider your transportation needs– for example the nearest bus stop to the White Plains Beach cabins is over two miles from the beach. Pokai Bay beach cabins are in Waianae, over an hour away from Waikiki. Kilauea Military Camp (on the Big Island) is near the middle of the island and at altitude– winter temperatures can dip down into the 40s. It’s also an hour away from Kailua-Kona and Hilo. Oh, and there’s a live volcano erupting nearby… but it’s been well-behaved for nearly three decades. No worries!

I’m sorry to say that camping in Hawaii may not be a fantasy experience. Camping is viewed as a way to “live at the beach” for quality fishing and surfing and partying, and evening noise can be a problem. Gasoline generators and sound systems can be an issue, and camp security is not always immediately available. Some state campsites and beaches have a persistent homeless population. The best tent camping I’ve experienced has been at White Plains Beach, Bellows Air Force Station, and Haleakala National Park. Camping in Haleakala is for hard-core backpackers only– at altitude, with no transportation or open fires or potable water.


Transportation, entertainment, & food

Part of the location equation is also transportation. If you’re in Waikiki then The Bus (or, as it’s more popularly known, “Da Bus”) will take you just about anywhere you want to go. Elsewhere on Oahu the nearest military base will have a car rental franchise (no airport taxes/fees). Car rentals on neighbor islands can be expensive, and unfortunately there are no RentAWreck franchises in the islands. Your maximum flexibility for minimum price in the more remote neighborhoods might be bicycles, scooters, and short-term rentals.

Once you’re here, entertainment is relatively cheap (especially outdoors). You’re living in one of the world’s biggest outdoor recreation areas where you’re only limited by water, sunscreen, and protective clothing. Oahu has an extensive network of bicycle trails (particularly on the North Shore and around Pearl Harbor) and every island has miles of hiking and beaches. If you don’t know how to surf, then this is the place to learn. Every beach rental franchise has someone available for a lesson, and military recreation areas (like White Plains Beach) will offer very cheap lessons from the lifeguards. Kayaks and stand-up paddleboards are also easy to learn, with different muscle groups and different reflexes. If you’re hooked then there’s a lively Craigslist market in used gear, and almost every surfboard shop sells reconditioned used equipment.

Living in Hawaii long-term means eating local. If you’re expecting a daily breakfast of box cereal and cow’s milk, then you will pay dearly for the privilege (especially on neighbor islands). Lunchmeat can be surprisingly expensive, too. Of course you’ll be able to find a wide variety of fish (both fresh & frozen) as well as local beef, pork, & chicken. Vegetables are plentiful & cheap, too, if you eat the local versions of greens & fibers. You can find potatoes but you could substitute yams or, for a color thrill, Okinawan sweet potato. Poi & taro products are an acquired taste but they’re easy to find, and rice is cheap. If you’re expecting to eat raspberries, blueberries, or cranberries then you’ll pay by the ounce. However, the islands grow strawberries and a surprising variety of the most exotic fruits you’ve never eaten, far beyond the typical mango & papaya options. Lilikoi, guava, lychee, and rambutan are plentiful at certain times of the year. One of your most entertaining local activities might be an hour browsing the local grocery store for menu ideas.

Restaurant dining can be expensive but there are plenty of kau kau wagons. Military bases, of course, offer commissaries and cheaper food courts. Grocery stores (outside Waikiki) help you handle your own cooking, but you’d be using loyalty cards and shopping for local foods. Hawaii has big-box store chains, too, but your lodging would have to have the storage for you to stock up on larger quantities.

Those Hawaii vacation options give you the greatest range of flexibility and recreation opportunities. But what if you’re willing to trade a little labor for your lodging and transportation?


Voluntourism and labor exchanges

The National Park Service has a wide Mainland network of volunteer labor and seasonal employment, and some of that is available here. Both Volcanoes National Park and Haleakala National Park have occasional temporary positions. If you’ve participated in this program on the Mainland then you may be ready to jump right in, but otherwise I’d advise spending a week or two at these locations exploring the programs and the facilities.

Hawaii is a popular destination for voluntourism, and most of them are outdoors working on the land or with wildlife. One of the most thorough summaries of organizations and opportunities is the Let’s Go Hawaii site, which links to other organizations and their programs. Unfortunately most of them are short-term projects, although if you’ve worked with a particular organization in other locations then you may be able to use those contacts to your Hawaii advantage. I haven’t personally worked with these organizations and I can’t vouch for their credibility or their popularity.

Another intriguing possibility is WWOOFing. By “intriguing” I mean “Sounds interesting but I’ve never done it; could be a lot of hard work.” “World Wide Opportunities on Organic Farms” is the parent organization for linking volunteers to agricultural projects in exchange for room & board. If you’re interested in sustainable living and permaculture then this is a wonderful way to learn the techniques and the lifestyle. In its harshest terms, if you’re able to weed for several hours per day then you have the rest of the day off with food & lodging. I found another review of Hawaii WWOOFing at the BootsnAll indie travel website.

If you’re willing to do your own networking then you can start at Help Exchange, where people and local organizations offer homes or nearby lodging in exchange for project work. Keep in mind that these tend to be private homeowners, businesses, farms, or monasteries looking for labor in exchange for room & board. While it’s extremely affordable, and you’re living in paradise, there will be a certain degree of occupational toil and drudgery. Again I can’t vouch for any of these organizations, and I strongly advise visiting them in person before making any decisions. This might be a good idea for your third or fourth trip to the islands, but I’d hesitate to make a commitment just based on a website and a phone call.

If you have more questions about these opportunities, or if I can make a drive-by visit on Oahu to a particular group or site, then please use the “Contact Me” box or send me an e-mail. I’d like to thank reader Chris for asking these questions. I learned a lot about these programs, and I enjoyed the research!


Related articles:
Lifestyles in military retirement: Living in Hawaii
During retirement: where do you want to go next?
U.S. Air Force Air Mobility Command
Armed Forces Recreation Center Resorts
Department of Defense Lodging
Armed Forces Vacation Club
Billy & Akaisha Kaderli’s “Retire Early Lifestyle”
Paul & Vicki Terhorst’s travel site
The “Wandering Wahls” blog

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About Doug Nordman

Author of "The Military Guide to Financial Independence and Retirement" and co-author of "Raising Your Money-Savvy Family For Next Generation Financial Independence."
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2 Responses to Lifestyles in early retirement: Hawaii long-term travel

  1. Janette says:

    Great tips. I haven’t tent camped at White Plains, but I have atayed in the barracks at Kilauea MC. Hawaiian Air runs a special around Halloween every year. Remember to check your local National Guard for hops. Ours flies to Hawaii at least once a week!
    I thought our last trip was it… Back in the planning mode….2014?

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