Live Your Best Island Life on Maui

Moving to Maui

Updated 10/13/2021: Having just celebrated my eleven-year 'Mauiversary', I look back and realize I knew nothing about Maui when I moved here! I had never even been to Hawaii or Maui before. Prior to deciding to move to Maui, I had been living in Jackson Hole, Wyoming and if you've ever spent much time there you know it's amazing, but year-round the weather and career opportunities can be challenging. So, I made up my mind to sell my car, pack my stuff, and start a new life on Maui really knowing very little about the island. 

Truth be told, I had lived in the Virgin Islands for a short period of time and knew a little about island life in general. I knew Maui had more opportunities and things to do than St. Thomas and that was really enough for me. I knew moving to Maui was for me and I wanted to live my best island life!

Listen to Your Heart

My desire to move to Maui was mostly instinctual. Something told me it was the right thing to do and it certainly has been. If I had only known how amazing Maui is I would have moved here much sooner!  We literally have sunshine and rainbows virtually every day on Maui, but like any great endeavor, there are still a few challenges to overcome and some ways to optimize your experience. Keep reading to discover the big three questions you should answer before moving to Maui. 

1. What Will I Do?

Fun Stuff On Maui

This question is really two separate questions. What will I do for work? What will I do for fun? 

What To Do For Work

If You're Retired

This is going to be easy for some groups. If you're retired or semi-retired, you're all set and yes, I'm a little jealous. You can focus on finding your favorite hobbies and groups to be a part of.

Work Remotely

If you're a digital worker or can work remotely, you're all set too. Working remotely will bring a few other challenges such as the time difference and always having an internet connection. All in all, being a remote worker on Maui is really a dream come true. Going for a quick surf session before getting behind the computer all day really helps to keep your personal batteries charged.

There isn't a definitive coworking space that I've seen that would have all of the things a typical remote worker is looking for, so you'll really want to find a home that you enjoy working from or find a good coffee shop. I like Sip Me in Makawao, Akamai Coffee in Kihei, or Cafe Cafe in Lahaina. 

Looking For Work on Maui

Maui has begun to recover from the extreme challenges presented by the COVID-19 pandemic over the last year and a half. However, restaurants and hotels are still having challenges and aren't fully recovered yet. Overall, the occupational landscape on Maui looks much better than it did 12 months ago and some favorite local restaurants like Da Kitchen, which shuttered their doors during the pandemic, are starting to reopen. 

The main types of work available for those looking for work on the island will be in the restaurant, tourism and hotel industry, healthcare, business services, or retail.

As real estate agents, the way we work has changed a lot since the beginning of the pandemic, but we are fortunate that the housing market is still very strong. Other professional service jobs are available in healthcare and we certainly need more teachers on Maui. 

So, once we've figured out how we can pay rent or buy a home on Maui, its time to discover the island and your favorite things to do. 

What to Do For Fun

Maui Moving Tips

While Maui might not have the best nightlife, there is certainly no shortage of fun and adventure. Being a majestic tropical island in the middle of the Pacific Ocean IS as cool as it sounds and there are so many fun things about Maui. Your job when you move here is to try them all and discover your favorites.

Enjoy Nature at It's finest

Spending time in nature, whether at the beach or at the summit of a 10,000-foot volcano, is a big part of island life and makes Hawaii the ultimate place to be for nature lovers. Of course, we have all of the great ocean activities like surfing, scuba diving, sailing, fishing, and snorkeling, all of which you should certainly try (unless you're a pescatarian and don't want to fish). 

Maui is also home to some other cool ocean sports such as kiteboarding, windsurfing, and foiling. Foiling, particularly with a wing, has become a very popular ocean sport recently and I definitely recommend giving one of these sports a try. You'll find that ocean sports create communities of like-minded people who like to play in the water and it's a great way to make friends. Even if you're not into water sports, you're sure to enjoy the dozens of awesome beaches for hanging out.

More Than Ocean Sports

Asides from ocean sports, Maui has a wide variety of awesome land adventures to hidden waterfalls, particularly along the Road to Hana as well as many secret spots around the island. Many different hikes are located all over the island in a variety of climates. For the remote workers moving here, it's great to take a mid-day break to go do a quick hike to break up the workday.  

If you're looking for a lot of nightlife, you're going to prefer moving to Oahu over Maui. Maui does have a lot of great bars and restaurants, but very few that have regular events or that stay open very late. The main places for nightlife on Maui would be the Triangle area in Kihei or Front Street in Lahaina, but it's still hit and miss.

Maui is more of a happy hour island with lots of great bars and restaurants having most of their action happening in the early afternoons, you've got to get to bed early to get up and catch some waves! On Maui, we like to grab a Pau Hana (after-work drink) or two at places like Maui Brewing Company in Kihei or Merriman's in Kapalua. If you're moving from a big city, the quiet nightlife may be one of the biggest adjustments you make. 

Is It Expensive To Live on Maui?

You'll be surprised that compared to many major American cities, the cost of living on Maui is comparable or even less.

The most expensive thing about Maui is the rent and real estate. Maui's median property prices are significantly higher than the mainland aside from downtown areas in major metropolitan cities like San Francisco, LA, or New York. This also means rent is high as well. You can be paying up to $2,000/month or even more in some cases for a 1 bedroom condo. If you search for deals and are patient you can find rooms for rent on Maui for around $1,000-$1,300 per bedroom. 

You'll never have to drive too far to get anywhere and gas is usually a dollar or so more than the mainland, especially if you have that Costco membership. Food will be significantly more expensive at Safeway and Foodland and it's always more economical to buy in bulk at Costco. You'll also find Costco has a great selection of local products as well as quality meats. It's easy to find a starter vehicle for very little, we call them "Maui Cruisers" and they are a great way to get around while you're still deciding if you want to on Maui long term. New cars are slightly more expensive than the mainland, but odds are you will drive a little less here too. 

If you don't go out and eat too much it's not as expensive to live in Maui. I'd say it's actually a little easier to save money here once you have all of your ocean toys and go spend your time adventuring and playing rather than going out and spending money at restaurants and bars.

2. What Part of Maui is The Best to Live?

This the big question. When you first think of moving to Maui, it's usually a very general idea of living close to the beach and walking everywhere. I was surprised by the amount of difference there is between living in different parts of the island. One of the things few people realize without experiencing it is that temperatures vary a lot around Maui and so does the distance to the beach.

Not everyone is looking for the same things when they look at the best places to live on Maui, every part of the island has a little something for everyone and ultimately, you're never that far away from the beach. However, it is amazing to be able to walk to the beach from home and always have that option available.

There are 6 general areas of Maui. The West Side, The South Side, Central Maui, The Northshore, Upcountry, and East Maui.

West Side

Move To Maui

The West Side of Maui feels like its own island. Approximately 45 minutes from the airport, West Maui includes Lahaina, Ka'anapali, Honokowai, Kahana, Napili, and Kapalua. Hawaiian town names are given by the Ahupua'a for which the territory belongs to.

An Ahupua'a is a Native Hawaiian land division that stretches from the ocean up to the mountainside giving each community its own access to the ocean as well as land for agriculture. This was important for Native Hawaiian communities to have access to all the resources they needed within their division of land and ocean access. 

The Lowdown: The West Side is great if you want to be close to the beach, surf, and resort jobs. There are also 4 great golf courses in Ka'anapali and Kapalua. Ka'anapali is perhaps the most popular tourist area on the island and Ka'anapali Beach has all the major hotels. Front Street has some nightlife and bars if you're into that. One of the great things about West Maui is the sunsets. You'll always a front-row seat for the sunset on this part of the island. Check out the top 6 West Maui condos here.

Pros: Beaches, surf, sunsets, golf, resorts

Cons: Can feel isolated from the rest of the island, small, and can get congested during the busy season. Very hot in Lahaina, you'll want AC.

South Side

Moving to Wailea Maui

The South Side of Maui includes Kihei, Wailea, and Makena. While West Maui has many great beaches, many people feel like the beaches of South Maui are where it's at. Big Beach is one of Maui's most famous beaches and is one of few large beaches on Maui that don't have a resort or homes developed close by. Makena is the least populated and most wildly beautiful part of South Maui, it's also home to some of the most luxurious real estate anywhere in the world.

The Lowdown: Wailea is primarily a resort and second home community with three great golf courses, several world-class beaches, and excellent restaurants. Kihei is a great place to live because rent and home prices are lower than Wailea, but you are just a short drive from Wailea and Makena. Kihei has a lot of great condo complexes and neighborhoods that are walking distance to the beach and a lot of fun activities. You're also really close to Kahului where you'll be going to make your Costco runs. Sidenote: A Costco membership is a must, you'll save so much money shopping there versus anywhere else. 

Pros: Close to the beaches, close to shopping, spread out with lots of things to do. Makes taking adventures to Hana or to Haleakala much quicker than living on the West Side. Great dry climate, particularly Wailea and Makena. 

Cons: North Kihei can get very windy and dusty. Traffic can get bad on the lower road.

Central Maui

When I first moved to Maui I definitely overlooked this area. I lived on West Maui for my first 8 years here, spent 2 more years in Kihei, and then finally moved Upcountry. I always wanted to beach lifestyle, but I've learned you can have the beach lifestyle from basically anywhere on the island. Wailuku and Kahului are the commercial and industrial center of Maui with quick access to the hospital, courthouse, shopping, and the airport. 

Central Maui offers some of the most comfortable and affordable places to live on the island and you're still within 15 minutes to the beach. You're actually close to a lot of different things living in Wailuku, close to the Northshore for surfers and wind sports enthusiasts, and close to the South Maui beaches for those chill beach days snorkeling and laying out. 

The Lowdown: Central Maui can't be beaten for having access to it all. If you're coming to work in healthcare, professional services, or a similar field, living in Wailuku or Kahului will make getting to work easy and keep the cost of living down. You'll be able to hit the beach easily as well. 

Pros: Close to everything, especially close to shopping, healthcare, and services. Slightly cooler temperatures on the Wailuku hillside in Kehalani and Wailuku Heights

Cons: Not walking distance to the beach. The most heavily populated part of Maui. 

Northshore Maui

Maui's Northshore

This is one of my personal favorite parts of Maui. The rugged Northshore coastline of Maui has some of the world's most amazing surf spots like Jaws and Ho'okipa as well as the famous wind sports beach of Kanaha. Paia town and Northshore Haiku make up what we call Northshore Maui and offer a cool, quaint active lifestyle community. This part of the island is leeward meaning that it is facing thousands of miles of open ocean and gets a lot of wind, great for kitesurfing! 

Living in this part of the island will give you quick access to the beach, surf, as well as the Road to Hana for those waterfall and cliff jumping adventures. 

The Lowdown: It's not easy to find good places to rent in Paia and it does get really hot here during the summer, many Northshore sports enthusiasts choose to live a little further Upcountry in Haiku and Makawao for better rent and housing. Spreckelsville is one of Maui's very best neighborhoods and if you can afford to live here, go for it! Sprecks, as we call it, is a really cool neighborhood right on Baldwin Beach with some of the very best athletes in Maui ocean sports calling it home. 

Pros: Get to the beach quickly. Walk around Paia Town and shop at Mana Foods. Enjoy the adventures along the Road to Hana. Still close to Central Maui shopping and airport. Close to Mama's Fish House.

Cons: Low amount of places to rent or affordable homes to buy. 


Kula Real Estate

The area of Maui known as "Upcountry" is also another often overlooked area when first deciding to move to Maui. Most of us move to Maui because we want to be a stone's throw away from the ocean or at least a short walk away. Living Upcountry does make getting the ocean a short drive, but it comes with other benefits living on the coast doesn't have.

If you like wide open space, expansive views, and slightly cooler temperatures, you should really look at living Upcountry. The communities of Haiku, Makawao, Pukalani, Kula, and Ulupalakua make up Upcountry Maui and the homes for sale and for rent in these communities offer more land, more space, and often bigger views than many other areas of Maui. There is a lot of character and charm to Upcountry Maui and if you're like me, you'll enjoy not having to have the AC on while you sleep as you might in parts of the island like Lahaina. 

With the recent addition of the incredible pizza at Marlow and the craft beers at Mahalo Aleworks brewery, Upcountry has become a little more outgoing. There aren't many places to go out for dinner or drinks and these two hot spots are a welcome addition in Pukalani.

The Lowdown: Upcountry is rural, laid back, and still close enough to the beach. You're 45 minutes from Wailea and 20 minutes to the Northshore. You're also just a short drive from the airport and of course, Costco

Pros: Great views, slightly cooler weather, beautiful pastoral landscape. You're close to Haleakala National Park as well as Poli Poli State Park and close the Northshore beaches and activities. 

Cons: Further from the beach than the South Side and the West Side, having a car and driving is a necessity, and some areas don't have great cell service (could be a pro if you're looking to get away). 

East Maui

Road To Hana

East Maui is technically the entire east side of the island which is all of the 10,000ft volcano known as Haleakala. But, when I refer to East Maui here I really mean Hana. Not as many transplants look to move to Hana when they move here except for those looking for a work-trade on a farm, which Hana has several that offer this. It's the most remote area of Maui, along with Kahakuloa, and is an hour and a half away from Paia on the Road to Hana side and about the same distance from Kula on the backside. 

Hana is one of the most beautiful and rugged places in all of Hawaii. It has some stunning scenery, a black sand beach, and a red sand beach. Many of the island's most iconic destinations are in Hana, but few rental or homeownership opportunities are here.

The community of Hana is more insular than the rest of the island and this has been highlighted during the COVID-19 pandemic as they actually closed outside access to the area for months, even to other Maui residents and locals. You'll most likely just want to visit Hana as opposed to calling it home.

The Lowdown: Hana is the ultimate day trip. Check out a number of amazing waterfalls and scenic locations on an all-day drive or go out for a weekend of camping at Wainapanapa State Park. It's a beautiful, rural community that chooses to retain its simplicity and slower lifestyle.

Pros: Off-the-grid living. Some of the most amazing beaches, scenery, and adventures anywhere in the world.

Cons: Not much cell service, very remote and far away from healthcare, shopping, or other island activities. 

3. Will I Get Island Fever on Maui?

This is a great question and one you should really consider. To me, Maui feels like home, and when I leave I get 'off-island fever', medically defined as the desire to return to an island!  So, what's it like living on an island, and what can cause island fever?

Living on an Island in The Middle of The Pacific Ocean

Maui's Beaches

Hawaii is actually the most geographically remote place on Earth. So, moving to Maui is moving a long way away from anywhere. Even if you're coming from California.

That's right, it is thousands of miles out here in the middle of the Pacific, meaning, that if you want to go anywhere besides Hawaii, you're looking at a minimum 5 hour(ish) plane ride. It's not easy to just pack up and go on a big multi-day road trip, one of the main things I miss about living in Jackson Hole. Maui isn't small compared to a lot of islands, yet you could still drive around the entire island in one very long day. 

I've never personally felt island fever on Maui, but I do miss friends and family on the mainland and the longer I've lived the less I've gotten to see a lot of great people I love back home. You will certainly want to establish new relationships and connections once you get here and it's really not too difficult.

Find Your Ohana

There are a lot of great people on Maui that do interesting and fun things and enjoy meeting new people too. The hard part is making friends here that end up relocating somewhere else, but it's all just a part of life. There are tons of groups that meet up for hikes, diving, surfing, golfing, and other activities.

You won't meet as many people in the traditional city way of finding them at coffee shops or bars, most people on Maui are out and about doing fun outdoor stuff, so get out there and make friends, and if you're reading this and still want to know more, you can always call or email me, my contact info is everywhere!

Develop A New Positive Routine

One of the absolute best ways to adjust to your new island life is to get into some new positive routines. Going for walks regularly on your favorite beaches, learning how to surf or scuba dive, or going to your favorite coffee shop regularly will ensure that you're getting yourself out there and meeting new people. This is especially true for remote workers than have everything they need to work and survive at home. 

Get creative with your workday or with all of your days. Find like-minded people and causes that motivate you. 

The Most Important Thing To Bring to Maui: Aloha

 Kihei Condos

This might sound a little funny to some because it's typically in Hawaii where one will find Aloha, but it's important to remember that everyone has Aloha and you definitely want to bring it if you want to be happy here. You will hear people say "This Ain't Da Mainland" and it really isn't. Maui still has a slower pace of life compared to the mainland U.S. and that's what most of us are looking for when we move here. Locals are extremely friendly and Maui will certainly embrace you if you embrace island life.

So, what are you waiting for? Come to Maui and live your best island life and if you ever need any pointers along the way, feel free to reach out to me and I would be glad to help any way that I can. 

Get In Touch

Evan Harlow Maui

Get started on your journey to owning property on Maui by getting in touch with us at Maui Elite Property. 

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Posted by Evan Harlow R(S) 82003 on


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Thank you for the detailed article. Well done, honest. Helping to soften my heart for possible relocation from Oahu to Maui

Posted by Christine on Wednesday, June 9th, 2021 at 10:11am

Aloha Christine, I'm glad you found the article useful!

Posted by Evan Harlow R(S) 82003 on Thursday, June 10th, 2021 at 10:17am

Enjoyed your phrase, " OFF island fever", because that is exactly how I feel every time I

leave one of the Hawaiian islands.

I have this longing to be and to live in Hawaii again. I miss the rich culture, aloha spirit, and

ono food.

You have stirred up great memories and added to my knowledge of Maui.

Mahalo nui loa and hope to see you soon,


Posted by Donna Jane Roy on Monday, October 4th, 2021 at 1:33pm

22 years here.
Come on bra. Your about 77 percent right. I know I just came across your article. The average T-11 sided home that needs major improvements $750,000. Something liveable $950,000
Thats not not practical for most. Plus the cost of getting your stuff there. The low rent rate you mentioned you if you look hard enough, I don't think you can get a place at Harbor Lights for that reasonable. If your moving to Hawaii from Detroit maybe Harbor lights would work. You forgot to mention that Maui is none as PIRATE ISLAND.

Posted by Paul on Monday, October 11th, 2021 at 3:30am

Aloha Paul, thanks for your are right, we need Maui county and the state to address the cost of living issue because even now median income can barely afford median housing, and with the trajectory of the market, it isn't sustainable. My article was written last September, so I just went in and updated it a little to be more current. I appreciate the C plus on the article though! I'm trying.

Posted by Evan Harlow R(S) 82003 on Wednesday, October 13th, 2021 at 11:19am

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