Moving to Maui, Living on an Island, Jobs and Affordability

Moving to Maui

Moving to Maui, Living on an Island, Jobs and Affordability

Being a realtor in Maui, I meet many people, most of whom are visitors. So I get asked the same questions alot. What is it like to live on an island? Do you get island fever? How can one afford to live here since the cost of living is so high?

I moved to Hawaii in 1999. First to Oahu and then to Maui in 2000. It has now been about 23 years, and I’ve raised 4 kids here in Maui. Maui is like no other and I can wholeheartedly say that it is a place that feels like home more than any other place. Prior to that, I lived in New York City for over 14 years and also spent time on Sanibel Island, Florida. I had visited the Grenadines numerous times and tried to find a way to make a life there. But it proved too difficult being outside the US. But I didn’t give up on making a life on an Island and Hawaii was the answer.

Sure, in the beginning, it was not easy. Actually, let me be more specific. In the beginning, it was easy! I felt like I was on vacation and in a dream. Playing with my kids on the beach, teaching them how to swim and surf, camping with them under the stars; how could I be happier? But once you realize you have to “find your life” here, then that’s when it started to feel “uneasy”. Back then, in 2000 the internet was real but not as prolific. I started an online fashion/decor business on my big Apple Mac desktop. I was in the fashion business and was still trying to keep ties to it. Maui was definitely not New York, and I didn’t know a soul outside of my own family. So you can say, I actually felt a bit “homesick”. I won’t go into all the details here in this blog. But as I mention below, it takes time to acclimate even if it’s paradise!




After showing a property in Makena, the sun was setting and I took this serene photo at Makena Landing Beach Park.

Maui Dreamin’: How You Can Make Your Island Living Dreams a Reality

This Hawaiian island paradise offers endless opportunities for relaxation, adventure, and natural beauty. But how can you turn your Maui dreams into a reality? In this blog post, I’ll share tips/ideas on everything from finding the perfect home to landing your dream job in paradise. So grab a pineapple cocktail (or flavored seltzer) and let’s dive into how you can make Maui living a part of your everyday reality.

Introduction to Maui: Geography, Climate, and Culture

Maui is the second-largest of the Hawaiian Islands and is often referred to as “The Valley Isle”, due to the large valley that is nestled between two mountains. Maui is about 48 miles long and 26 miles wide, with a total land area of 735 square miles. The island is made up of two volcanoes, the West Maui Mountains and Haleakala, which form Maui’s dramatic landscape.

The climate in Maui is diverse. It has many subclimates and is in my opinion one of the most delightful things about Maui.  Where can you go from 85 degrees Fahrenheit to 50 degrees in about an hour? From rain to the sun just around the bend? Plus rainbows! From desert-like plants to lush rainforest within an hour? Maui is so incredibly unique.

To be overly simplistic, here is a short explanation of how the weather is made on a typically warm day in Maui. Trade winds carry moisture-laden air up the northeast slopes of Haleakala Mountain. As the moisture rises, it cools and condenses into the cloud layer that frequently circles the mountain. Rising warm air often pushes the clouds up through Ko’olau Gap and Kaupo Gap. As the temperature lowers in the evening, the clouds go down the valley and the cycle begins again.

Haleakala Mountain impacts the weather all around it.  Average annual rainfall varies from about 400 inches (10.16m) in the high-elevation rain forest above Hana to 10 inches (25 cm) in Kihei, only about 15 minutes apart. Because temperatures drop about 3.2F (1.3C) every 1,000 feet (305m), the summit of Haleakala is roughly 32F (13C) cooler than the beaches. These are past averages. To read more about rainfall, and climate on Maui, please refer to my prior post here.    

Moving to Maui Guide

Very quick snapshot of what you can expect weather-wise (non-scientific! Just my observation from living here):

South Maui: (Kihei, Wailea, Makena) Drier, sunnier warmer area. Considered leeward side.

West Side: (Lahaina, Kaanapali, Napili, Kahana, Kapalua) Lahaina tends to be a drier, sunnier, and warm area. Tends to get a bit wetter as you go towards Napili-Kapalua area.

Upcountry: (Kula, Keokea, Pukalani, Makawao, Olinda). Cooler. How cool, depends on elevation- the higher you go the cooler it gets. Homes at high elevations may need a heat source, especially during winter months! Makawao/Olinda tends to be rainier than Kula. Keokea tends to get more rain than Kula. On the top of Haleakala Mountain, it can snow! Although it is a national park so no homes but just to give you an idea of the climate. The mountain is just over 10,000 ft!

Central: (Wailuku and Kahuli): Not sure I would call Wailuku central because there is part of Wailuku that goes up the West Maui Mountains they definitely get more rain than the central valley of Kahului. Kahului is dryer and warmer.

North Shore: (Paia, Haiku) Can get windy as the day wears on (the reason why it is world class windsurf spot!). It is rainier than the dry areas like South shore of Maui. The rain tends to be more consistent inland/higher and farther east you go.

East Maui: (Hana) Semi-tropical rainforest. So it’s wetter. But ohhhhh that means lush, green and so magical!

Maui Climate

Maui is known for its glorious beaches but there is much more diverse beauty here. This is a photo I took recently at Kealia Pond which is National Wildlife Refuge.

Maui is home to a diverse population, with people from all over the world calling the island home. The island has a rich culture steeped in Hawaiian history and traditions. Don’t think that culture is just what is presented in the brochures. The culture is much deeper and varied. When you live here, you can take time to learn and experience it in a more holistic manner. Family (ohana), respect for one another, and the environment is held with reverence. I would encourage a visit to Hale Hōʻikeʻike at the Bailey House to learn more. If you are on Oahu, then the Bishop Museum is a must!

I will also be writing about the areas and towns of Maui and give you my take on them. So stay tuned for later posts. You can subscribe to be on my newsletter!

Maui Real Estate: Three Things to Consider Before You Buy

If you’re thinking about purchasing a property in Maui, there are a few things you should know before buying. The first thing to consider is your price range. The median price for a single-family home in Maui is $1,150,000 (March 2023). For Maui Real Estate Statistics and Market Report, click here. Secondly, you’ll need to think about what area of Maui you want to buy. I would recommend considering your lifestyle. Are you a beach person, who likes walks and swimming on the beach? Or do you surf, kite or windsurf and want to be close to those surf breaks and windsport-conducive areas? Or maybe you are a mountain person and prefer cooler temperatures? Or maybe you want to have a garden or be more remote? Maui is an island but an island with many options!

Secondly, what type of property you’re looking for? Do you want a condo, a house, or raw land? If you would like a condo, then what kind of amenities? Also in purchasing a condo, there are two main types: fee simple and leasehold. Also, do you prefer short-term rentable or long-term rentable? There are pros and cons to each option, so it’s important to do your research and figure out what’s right for you. Better yet, find yourself an experienced trusted real estate agent (that is client focused)  to help you navigate the many details of buying real estate on Maui! Another consideration is where will you be working (unless you do not need to work, then congrats!) and how close you want to be to your place of work. For instance, if your job is on West Maui, then it is highly recommended that you live in West Maui, due to the unpredictable traffic on the Na Pali coastline highway. If the west side is too expensive, then I would consider the Wailuku area if you are working on the west side for “easier” commutes.

Now keep in mind before making the decision to buy a property, you may consider renting.  Sometimes this makes the most sense as it gives you time to get to know the island as a resident (very different than as a visitor) and get a better feel for what you want. HOWEVER, sometimes this is not the best option. I had a client who felt that if he had bought 2 years earlier, he could have saved a lot of money since real estate prices and interest rates went UP! So renting is not always the foolproof plan. This is a decision you will need to make, as markets and obviously life events are not easy to predict. But a wise investor once told me long ago “don’t wait to buy real estate, buy real estate and wait!”. Of course, you need to do what is most comfortable for you and that you can afford.

Jobs in Maui: Finding the Right Fit for You

When it comes to finding a job in Maui, there are a few things you need to keep in mind. First and foremost, the island is a tourist destination, which means that many of the jobs will be in the hospitality industry. However, there are also a number of other industries represented on the island, so you should take the time to research which businesses are operating in Maui and see if any of them are a good fit for your skillset.

Another dominant industry in Maui is the healthcare industry. From doctors, nurses, health technicians, physical therapists, psychiatrists, and so on.  It’s not just the actual occupations but the need for skilled labor to address the equipment and its ancillary offshoots that are most likely in need.

In addition to the healthcare industry is the Health and Wellness industry which encompasses many modalities such as therapeutic massage, acupuncture, and naturopathy, just to name a few.

Maui does have a high-tech performance center. Read the article here.

There are also government, county, state, and federal jobs. Click here for info on Maui County Jobs.

There is the University of Hawaii, Maui College Campus. Click here for one of the resources. 

On top of Haleakala is what is dubbed “Science City” which is Haleakala Observatory (unfortunately it is not open to the public) but if this is your field then this could be a very interesting place to work. They were responsible for unveiling the biggest digital map of the universe! For more info on Haleakala National Park click here. 

However, now with the rise of remote jobs, the location may not be such a big factor except for the need for reliable internet. Perhaps you have dreamed of starting your own business and being an entrepreneur. From energy, restaurant, food products, high tech, agriculture and etc maybe it’s time to fuel that passion of yours. Maui County has a Business Resource Center Maui County even offers a “Starting a Business in Maui County” resource book, click here. 

I am sure that I have left out other ideas on jobs and work, but this should give you a start.

Making Island Life More Affordable 

Island living doesn’t have to be a pipe dream. With a little bit of planning and creativity, you can make your Maui dreams a reality. Here are a few tips for living on a “budget” in paradise:

  • Eat like a local. Dining out can be expensive, so take advantage of Maui’s incredible produce and cook at home as much as possible. Farmer’s markets are a great place to stock up on affordable, fresh ingredients. Quality vs. quantity. Better for your overall health too! Consider a Costco membership and stock up on bulk items that you readily use!
  • Take advantage of free awe-inspiring activities. From hiking and swimming to stargazing and taking in the sunset, there are plenty of free things to do on Maui. Get out there and explore!
  • Maui island culture doesn’t put a high priority on having the latest fanciest car, And yes, trucks are popular here in Maui. For many reasons, one being the hauling of water sports gear like surfboards. Having a good reliable car is very important. Gas is more expensive here than on the mainland. But it’s likely that you won’t be driving as far. EV cars are more popular now and especially energy efficient if you plug them into a solar-powered off-grid system. Try to walk or bike as much as you can, especially if there are good bike lanes (always with caution) or sidewalks (for walking).
  • Shop Less! No need for winter clothes. No heavy coats, winter boots, snow tires,  etc. So simple, comfortable, natural, and breathable fiber clothing is best in our warm weather. Of course, a swimsuit and flip-flops is a must!
  • Even if you don’t need to be “budget conscious” it still is nice to eat fresh locally grown food, and just enjoy one another and nature more…

It’s all relative, right? I came here from NYC over 20 years ago and for me the cost of living didn’t phase me because I was use to NYC prices. But I know its not inexpensive to live on Maui. Gas, food, electric is higher than many places on Mainland USA. Here is a good website I found that gives you estimated cost of things on Maui. I checked many of the prices and they seem to be in the ballpark. Click here. 

Does one get “Island Fever” living on a rock?

Well, I can only speak for myself. But no, I don’t get island fever. First of all, Maui is just 5-6 hours away via current plane travel to the west coast of the US. Non-stop- easy! Also, I can go to other islands like Kauai, Oahu, Lanai, Molokai, or Big Island. Believe it or not, they are all very different islands. Or I also remind myself that I still have not explored all of Maui! Spend the weekend in Hana or a day in Kapalua. I have yet to camp at the cabin at Haleakala Crater! I have not yet snorkeled every great spot on Maui either. Also with the age of computers and high-speed internet, so much is available just at my fingertips.

Living PONO

I don’t want to get preachy or didactic here. I am sure you don’t want to hear from a realtor about how to live your life. But this subject is important so let me just say this… as much as the brochures want to commercialize “aloha”; the true aloha and living “pono” is alive and well. I have witnessed it and see it almost every day. Whether it is someone kindly letting you make a left turn onto a busy road or just waiting a bit and not instantly resorting to honking, it alive and well.  Sure… there is always room for improvement but don’t overlook the importance of Pono. Pono is multi-leveled and deep so I won’t by any means try to explain it all nor do I profess to fully understand its meaning. It is more of an aspiration to bring respect, correctness, balance, and harmony to one’s actions. Again, this is just an overly simplistic explanation. If you have an interest, I would suggest exploring deeper into this meaning.

A very general introduction outline of culture/values was nicely presented by Hawaii Tourism Industry. You can read it here. 

Hula at Hui No'eau at Annual Art Exhibit 2023

I took this photo of the beautiful and culturally significant Hula at Hui No’eau at the Annual Art Exhibit 2023

Creating Your Dream Here in Paradise

Island living is a dream for many people. The golden-sand beaches, azure waters, and year-round warm weather are just a few of the reasons why. A change of location can be amazing, especially if it is on an Island like Maui. But don’t delude yourself that location is the cure-all. Your mindset, your outlook, and your willingness to be open to a new place, new people, and a new environment will be more important (in my humble opinion) than anything else. It takes time to find your “home”. I tell my clients who move here to give it at least 2 years. First-year, you may still feel like a tourist, trying out all the new restaurants and tourist spots. It is the 2nd year where the acquaintances you met may become friends, where you find your rhythm, your go-to spots for swimming or walks. The people feel more familiar because YOU are more familiar. It’s been said that our brains are wired for survival, so the brain tends to point out potential hazards; the “unfamiliar”. Having said all that, for some, Maui simply is not their place, and that’s totally fine too. But before you make that conclusion, I would suggest you give it some time.

For some, meeting people is just not easy. So, my suggestion is to just go do things you love or want to do; whether it’s taking an art class at the Hui No’eau art center, dance lessons, continuing education at the University of Hawaii, Maui Campus, surf lessons, diving lessons, and so many other things. Or VOLUNTEER! Maui has an incredible website where you can look up organizations and sign up to volunteer. It could not be easier. I use this website regularly. It’s called Hands on Maui.  Click here!

Here is a post I wrote about volunteering on Maui. Great way to meet people as well. Click here. 

Oh, and you can try out the latest craze-Pickleball! I don’t want to offend tennis players out there so please excuse me… but I have never seen a sport get this hot- this quickly! I will be writing about pickleball on Maui in a later post. But there are county courts and private courts. I play at Wailea Tennis Courts and have met so many new people. There is a pickleball league as well. Email me if you want info on pickleball

Here is a great test. You fly to the mainland and spend some wonderful time with family and friends. You go to all the places you can’t find in Maui, like certain museums, stores, and restaurants. It’s time to go back home to Maui. You get on your plane, and you recall the great time you had and that you had to buy extra luggage to bring back all those items you can’t get on Maui (although Amazon has done a good job!). Your plane lands at OGG (Maui airport). You deplane and walk into the open-air airport and you feel the warm moist air and it feels soft and sweet…you just realized you are so glad to be back. To be back home… and slowly but surely Maui has gotten into your soul, and you feel so lucky that Maui is your home. Your home base…. aloha…welcome home.

Maui Aerial on Cessna Plane with my son as the pilot.

There is so much more about moving to Maui that I could probably write a book, but right now being a realtor on Maui takes up most of my waking hours. So if you want to chat about it, feel free to give me a call and we can simply start with a friendly conversation. f you are looking to buy/invest, then we can certainly have a meaningful conversation about what that entails. If you want to sell your Maui property then we can discuss how to (and my experienced marketing advantage!)  and the difference between selling as an in-state or out-of-state owner. Whatever you need regarding Maui real estate, I am here to be of service. But hey, if you just want a great restaurant recommendation, well I think I am good for that too!

Have a great aloha day wherever you are on this planet!

In future posts, I will be writing about areas and towns of Maui and give you my quick takes and summaries. Stay tuned and subscribe!

For now, if you want to look up real estate in certain areas of Maui, click here and you can see the Map of Maui. Just click on different areas on the map and it will take you to that area for listings. You can also create an account and save your searches. Go

Bringing Pets to Maui. Go to here. 

A hui hou…and mahalo.

Jeannie Kong-Evarts. Voted by her colleagues she is a prior recipient of Maui Realtor Salesperson of the Year, the highest award given by the Realtors Association of Maui.

All photos taken by Jeannie Kong-Evarts unless otherwise noted.

Maui's best realtor


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