Try Living In Hawaii For A Week

So you’ve already thought carefully about the impact a move to Hawaii would have on your family, and you’re OK with any sacrifices you’ll have to make. And you’ve done some research on the different Hawaiian Islands and narrowed it down to one or two that you think would best suit you and your family. You can’t wait to pack everything up and move to paradise.

But before you spend lots of time, money, and effort uprooting your life and moving it all overseas, it’s important to make sure that you really do want to live in Hawaii. At this point, that may sound like a no-brainer. But sometimes people think they want to live in Hawaii, but what they really want is to be on permanent vacation in Hawaii. What they love about coming to Hawaii is not necessarily unique to Hawaii itself, but being able to get away from the daily grind of waking up early, commuting to work, making dinner, cleaning the house, taking out the trash, helping the kids with their homework, etc.

Unless you’re fabulously wealthy and can afford to move into a suite at the Trump International Hotel, where your every need will be taken care of by their attentive staff (a girl can dream, can’t she?), your daily life in Hawaii probably won’t include maid service, room service, breakfast buffets, or a work-free schedule.

To make sure you really do want to be a Hawaii resident (and not just a permanent tourist), you should plan a trip to the Hawaiian island that you think you’d like to eventually move to — at least a one-week stay. If you can afford it, stay longer. If you’re not totally sure which island you want to move to, you’ll probably want to stay longer so you can do some island hopping.

Everyone who is part of your planned move to Hawaii needs to come along on this trip. But don’t think of it as a vacation. Your goal for the week you spend in Hawaii will be to live your life as close to the way you do now in your current home.

Accomodations | Transportation | Essential Tools | Daily Routines | Daily Explorations | Leisure Time | Reflection Time


Choose accomodations that match your current lifestyle and financial means. If you currently live in a detached house, ask yourself if you would be able to afford such a house in Hawaii. Check current real estate listings to make sure. If you discover that you’re more likely to be living in a condo, townhouse, or apartment, then that is the kind of accommodations you’ll want to seek out. Short-term condo rentals are not hard to find, and some are even cheaper than hotel rooms.

If you’re still able to afford a detached house in Hawaii, then try to find a rental house to stay in. This can be a challenge, though, as listings for short-term/vacation rental houses tend to be high-end, luxurious beachfront estates with sky-high nightly and weekly rates.

Most budgets will require something less expensive, and unfortunately detached houses in a lower price range are hard to find as short-term rentals in Hawaii. You might need to settle for a condo or hotel room instead.

Here are some good places to find all kinds of short-term rentals in Hawaii:

  • Airbnb: Whether you’re looking to spend $29 a night to sleep in someone’s living room or $4,000 a night to stay at the Kailua estate where the Obama family spends their winter holidays, there is something for every budget on this awesome site. (Why I’m not recommending Airbnb anymore.)
  • Craigslist Hawaii: Check out the listings under “Housing”: “Sublets/Temporary” and “Vacation Rentals.” You might want to also look under the general “Apts/Housing” category, because sometimes people post listings for short-term rentals there, too.
  • Honolulu Board of Realtors: This site includes rentals for all islands, although at the time I checked it, most of the listings were for Oahu. Still, it’s worth a try if you’re looking to stay on another island, as there are some relatively reasonable prices on here. Just be aware that this site also lists long-term rentals, so be sure to select “Short Term” or “Vacation” (under “Rental Type”) when conducting your search. Prices listed in the search results could be monthly or nightly rates, so read the details of the listing to find out which it is.
  • Aloha Living: This real estate site has a very handy search tool for finding vacation rentals by island, region, type of housing, size, and price range. (Note: Even their “budget” rentals can be pretty pricey, so you might want to start searching at that price range.)
  • Vacation Rentals By Owner: VRBO’s listings can be daunting — many of the listings are for outlandishly expensive oceanfront luxury homes and estates. However, if you dig deep, you’ll find some smaller, cheaper rentals, too, especially condos in Waikiki and the rest of Honolulu.
  • Polynesian Plaza: If you’re planning to stay on Oahu for a longer period of time, this place has one of the cheapest monthly rates I’ve seen online: $1,175/month for April-October 2011.

If you can’t find any short-term rentals that fit your budget, there’s nothing wrong with staying at a hotel. Just make sure the hotel you choose isn’t much more luxurious than the kind of home you’d be able to afford in Hawaii, and try to avoid using services like in-room dining, which you wouldn’t have in your home.

Before I moved, when I tried living in Hawaii for a week, I ended up staying at the modest but clean Park Shore Waikiki, located on the quieter eastern end of Waikiki, right across from Kapiolani Park. The room was comfortable but basic, containing no luxuries that I didn’t have in my own home. And the free Wi-Fi Internet access in the lobby was very handy to have.


Most likely you’ll want to rent a car — just make sure it’s the kind of car you’d be able to afford in “real life.” But if you envision using another form of transportation if you move to Hawaii, then you’ll want to try using that instead. If you like the idea of getting around by moped — a very popular form of transportation in Honolulu, where parking can be scarce and costly in some areas — then you should rent one of those instead of a car.

When I was planning to move to Hawaii, I decided I wanted to try living without any vehicle at all. So during my one-week stay, I walked and took the public bus everywhere, just as I would when I eventually moved.

Essential Tools

To make the most of this trip, it’s important to have three tools at your disposal:

Laptop or other portable device that can connect to the Internet. It would be ideal if you could connect to the Internet without having to rely on Wi-Fi (like with a 3G- or 4G-enabled smartphone, or with a broadband USB modem that you can plug into your laptop), but connecting via Wi-Fi will work, too. If you’re going to be relying on Wi-Fi, you should book accommodations that have Wi-Fi access, so you have at least one place you can count on for connecting to the Internet.

Free Wi-Fi hotspots can also be found at Starbucks coffee shops, Barnes & Noble and Borders bookstores, and even some McDonald’s locations. If don’t currently own a laptop or device that can connect to the Internet, you can make a reservation to use a computer at a Hawaii public library branch for free, or you can pay to use one at an Internet cafe, FedEx Office, or The UPS Store. Some hotels also offer pay-as-you-go Internet service.

And although I don’t recommend using this as your main method of connecting to the Internet, I’ve used it in a pinch: If you happen to be close to one of Honolulu’s three Apple Stores, you can use one of their demo laptops to quickly look something up.

When I was exploring Hawaii before my move, I used the Internet multiple times a day to look up rental housing listings, email landlords to schedule viewings of homes, map addresses, look up bus schedules, find locations of Wi-Fi hotspots in certain neighborhoods, and more. I suppose I could have used a local newspaper and a telephone to do most of that, but it would have taken much longer and I would have gotten less comprehensive information. Having Internet access will greatly help you accomplish everything you hope to during your “Daily Explorations”(see section below).

GPS unit or street map. If you have a portable GPS unit like a TomTom or Garmin, I recommend bringing it with you on your trip, even if you’re not planning to rent a car. It will save you tons of time and frustration in trying to find your way around unfamiliar territory. If you don’t already have a GPS unit, then I recommend buying a detailed street map once you arrive in Hawaii. If you have a handheld device (like a smartphone) with Internet access, that will work, too — you can just look up directions using Google Maps whenever you need to.

Camera. A picture truly can be worth a thousand words, so taking photos (or shooting video) is a quick, easy, and efficient way to document anything you want to remember from your trip: neighborhoods you like, neighborhoods you don’t like, local schools you toured, homes you viewed, etc. To help you document the places you visit, here’s a simple trick I picked up from my friend Vera: Before you start taking photos of a certain area, try to find an indentifying marker, like a street sign or entrance sign, and make that your first shot, so you’ll remember the location of the photos you take after that.

Daily Routines

During your stay, try to stick to your normal daily routines as much as possible: Make meals at home, go grocery shopping, do homework, run errands, tidy up after yourselves. If you have a fitness routine, stick to it as closely as possible. If you normally go to a gym, see if you can find one in your area that you can pay a daily or weekly fee to go to. If you normally attend religious services, try to find a local church, temple, or mosque that you can go to.

Assuming you currently have a job, try bringing some of your work with you on your trip. Do a little work, perhaps reading and responding to your work email, on each of the days you’d normally be at your job. If you have kids, have them bring schoolwork that they can work on each day. You don’t need to spend eight hours a day working (in fact, you’re going to need time during the day to do your daily explorations — see below), but you do want to preserve some sense of your normal daily life during this trip, and going to work or school is a significant aspect of most people’s lives.

Daily Explorations

Since you won’t be able to go to work and your kids won’t be able to go to school, use that time during the day to explore different residential areas of the island. If your accommodations are in a tourist area, it is especially important to get out of there during the day so you can experience where the residents live. Depending on the length of your stay and your family’s needs and interests, you may want to use your daily exploration time to:

  • Visit different neighborhoods in cities or towns that interest you. As you explore these neighborhoods, mentally go through your daily and weekly routines, placing yourself in that location. Ask yourself things like: If I lived here, where would I shop for groceries? Where would the kids go to school? Is there a gym nearby? How long would it take me to drive to work? Does this environment uplift me or depress me? Can I picture myself meeting people and making new friends here?
  • Attend open houses of homes for sale that are within your price range. You’ll get a true sense of the kinds of homes you can afford to buy in Hawaii. Find open houses on Oahu, the Big Island & Kauai (check the “Open House” box), and Maui, Molokai, & Lanai.
  • Tour homes or office/commercial space for rent. View listings for rental housing or commercial real estate.
  • Meet with a local real estate agent/broker. Hawaii Business Magazine’s annual Top 100 Realtors list might be a good place to start looking for an agent/broker in the islands.
  • Check out PreK-12 schools for your kids. Search for a public school or private school. If you time your visit just right, you can attend private school open houses. Honolulu Magazine offers more info on Hawaii’s schools in its annual Grading The Public Schools chart and Private School Guide.
  • Visit children’s daycare centers. PATCH is a statewide child-care referral agency that can help you locate daycare options throughout Hawaii.
  • Tour college and university campuses. University of Hawaii has 10 campuses throughout the islands. On Oahu, there are three private universities: Hawaii Pacific University, Chaminade University, and Brigham Young University Hawaii. If you plan your trip for this November, you can check out the annual Hawaii College and Career Fair, which is held on Oahu, Maui, Kauai, and the Big Island.
  • Go to local farmer’s markets. It’s a fun way to experience community life here in Hawaii, plus you’ll probably encounter foods you’ve never heard of or seen before. Find a location.
  • Visit public libraries. Hawaii has one large statewide public library system made up of 51 branch libraries. Find a library branch in your area (click the name to see its hours of operation).
  • Time a morning/evening commute. If you’ve identified a specific neighborhood you’re interested in and already know the general area where you’d probably be working, try driving between the two points during the times of day you’d be commuting to see how long it takes. This is an especially good idea if you’re planning to move to Oahu, which is known for having some pretty grueling commutes to and from downtown Honolulu, where most jobs are located. If you absolutely hate long commutes to work, this test may save your sanity in the long run. And with gas prices currently above $4.50/gallon here, avoiding a long commute will save you money as well.
  • Attend a job fair. If you’ll be staying on Oahu, Success Advertising Hawaii holds the biggest job fairs on the island three times a year. Also on Oahu: the annual Pearl Harbor Apprenticeship and Engineering Career Fair in March and the annual TechJobs Hawaii job fair in December.
  • Visit a career center or employment agency. Hawaii One-Stop Centers offer job-search assistance at locations on Oahu, Maui, the Big Island, and Kauai. Hawaii Small Business Development Center Network has centers on Oahu, Maui, Kauai, and the Big Island that offer free one-on-one counseling, in-class workshops, and online training, as well as the Hawaii Business Research Library on Maui. ALTRES is Hawaii’s oldest and largest employment agency for office, medical, technical, and industrial jobs. Kahu Malama Nurses is one of Hawaii’s largest nurse staffing agencies, with job opportunities for nurses, medical and nursing assistants, emergency and operating room technicians, and other specialty medical personnel. LAM Associates is a recruitment agency for physicians, physician assistants, nurse practitioners, pharmacists, and more.

Leisure Time

Just as you would in your “real life,” make sure you take time to relax and have some fun. Although this trip isn’t meant to be a vacation, you do need to have some downtime each day. Hawaii residents even have a specific term for this: pau hana (“done work”), and it represents a philosophy that’s very much a part of the local culture: that life is meant to be enjoyed after the day’s work is done, especially in a place as beautiful as Hawaii.

Otherwise, why bother living in Hawaii at all? So after your daily explorations, take some time to hit the beach, play a round of golf, hike a trail, indulge in some retail therapy, see a movie, or try a local restaurant — whatever floats your boat.

Reflection Time

Each day, discuss as a family your thoughts and opinions about that day’s exploration. Did anything make a positive/negative impression on you? Do you have any worries or concerns? Did anything surprise you? What adaptations do you foresee needing to make if you follow through with your plan to move to Hawaii? Consider taking notes during or after your daily explorations, while these thoughts and opinions are fresh in your mind.

After you’ve returned home from your trip and have settled back into your normal daily routines in familiar surroundings, see if any other thoughts come up about your recent trip. Do you find yourself missing something in particular about Hawaii? Or are you relieved to have gotten away from something there? Are there things about your current home/life that you appreciate more now?

Your trip may prove to you and your family that living in Hawaii is everything (or almost everything) you’d hoped it would be. It may also reveal some potential problems that you’ll have to deal with. Or you may discover that Hawaii is a place you’d rather visit once a year, instead of living there permanently. No matter what the results of your trip are, take heart in knowing that you gave living in Hawaii a try, and the life path you choose will be the better for it.