How to Move to Hawaii and Thrive: Maui Edition [Updated 2021]



How to Move to Hawaii and Thrive: Maui Edition [Updated 2021]

Seven years ago, I came to Maui, Hawaii thinking I would be there for a few months. When those few months were over, I pushed it back a month. And then another month. And then another. I started asking myself, what can I do to live here? I was starting thinking about how to move to Hawaii. It's much more expensive than a lot of places in other states.

Living on the island is a huge difference than living on the mainland. We're still part of the States, yes, but there's a completely different feel about living in Hawaii compared to the mainland USA.

Are you thinking about moving to Hawaii? Want to smile every day in the sunshine and to go surfing before work and watch the sunset on the beach after you grab dinner?

Want to get out of the daily grind of daily life?

Moving to Maui might be for you :). Although, there aren't many people it isn't for. 

I've put together a guide of what I've learned trying to figure out how to move to Hawaii and Maui and a lot of tips that have helped me along the way.

Major things to think about

Why Maui?

There are a handful of things you'll need to think about if you're thinking of moving to Maui and Hawaii. One of the big ones is which island to move to. There's Oahu, Maui, Kauai, Big Island for the main ones and then there's Lanai and Molokai as well.

Maui, the Valley Isle

Maui is the best of all world and is easily my favorite of the Hawaiian Islands. It has enough going on that you're not stuck in the jungle (if you don't want to be) but you can easily get to the jungle if you're looking for a play day.

Oahu is very busy and populated. It is the home to Pearl Harbor and all of the main military bases on the islands. Oahu is great for people who want tropical but also want the big city too. 

The highway on Oahu, the H1, is often compared to Los Angeles' highway and the amount of traffic between the two is also pretty close. Where Maui has essentially one road that will get you around the island, Oahu has five-lane traffic in many parts of the island. The big city amenities can be nice but you don't come to Hawaii to feel like you're in LA.

How busy Oahu is compared to Maui is about how busy Maui is compared to Kauai. You're taking a step down and back when you're on Kauai, which is part of the appeal. For me, Kauai is my second favorite island but don't expect to have an action-packed and busy trip on Kauai. You breathe, relax and enjoy life on Kauai, but you're relaxing a lot. Maui is a nice combination between Oahu and Kauai.

Big Island is big enough that all of the islands combined could fit in the amount of land that Big Island spans. It has cities and you can also get into the jungle too. For those who don't like feeling like they're on an island, Big Island is big enough that you might feel like you're not. You still have the tropical paradise of Hawaii though.

That being said, Maui is my favorite island, hands down. You get a slice of everything all of the other islands have to offer and for me, it's the perfect place.

Where Can I live in Hawaii and Maui?

Housing is another thing you'll need to think about. Some people move to Hawaii with the thought in mind of living on the beach. If things don't end up working out, they'll just sling up a hammock between a few palm trees and live a little be free-er life.

While that doesn't always pan out like they may think, there are some people who have built a home out of a van with solar panels, a bed, a generator and electricity.

This will only work for a very specific type of person. Living out of a van, even if it does have a bed in it, can get really old, really quickly.

You can find a place to live on craigslist, facebook or even the newspaper. If you're looking to go a more official and nicer route, you can go to a realtor to lease a condo or home but you're probably paying a little more and committing to a longer time investment.

If you can afford a home, you will be set. Homes on the low end cost around $600,000 and go up from there. If you can afford that though, you can rent out rooms in your house long term and have your tenants pay your mortgage. You would be better off having a separate unit for yourself and your tenants but again that depends on the type of person you are.

How Can I Afford to Move to Hawaii? 

You need a way to make money, whether it's a job, career, hustle or your own business.

One of the biggest industries on Maui is tourism. There are tons of jobs in hospitality and the service industries and a lot of the jobs can be really fun jobs. You can work as a zipline guide, give horseback tours as a ranch guide or even crew on a sailboat or a zodiac.

They say if you love what you do, you never work a day in your life. Maui is full of jobs that will help you work less. After all, the jobs you could be working are things people are paying a lot of money for just to come there and do. 

You could get paid to do them!

The pay for many of the jobs would be considered good pay on the mainland. Maui is expensive though, so making a decent wage in comparison to the mainland doesn't necessarily mean great pay on Maui. There are a lot people who end up working a couple or few jobs, just to make it work on Maui. It can be hard to get ahead.

That's why it helps to get a job that has benefits other than pay.

Restaurant jobs often give you a meal after work a partial or full shift. Getting a free meal on top of working will help a lot when it comes to saving money.

Boat jobs often give you a meal too, since whatever food is on the boat can't be reused the next day.

If you're young and you don't have a career, it's a great time to visit Maui but expect to work hard to be able to afford life on the island.

Many jobs that are available to those without higher education don't pay enough to support you for the higher than average cost of living on Maui. Don't expect to get just any job (retail or grocery clerk, for example) and be able to afford Maui.

How Can I Get Around the Island?

You'll also need a way to get around. Some people will only need a bicycle which you can definitely make work if you live near where you work. The weather on Maui is pretty consistent and it's consistently nice.

For example, if you work in Kaanapali on the west side of Maui, you could get away without having a car and using a bike if you lived in Lahaina.

Public transportation is surprisingly reliable too, but keep in mind that it takes a long time to get from one side of the island to the other.

If possible, even if you do want to have or get a car on island, live close to where you work. Not only will that reduce on your commute, it allows for you to walk, run or bike to work. 

Even using a moped to get to work is a great way to do it. 

Gas is expensive in Hawaii and if you can minimize your gas expenses, you'll be able to save more money.

On top of that, you'll get a little exercise and stay healthier if you're biking or running to work. After all, one of the reasons you're probably moving to Maui is to be outside and enjoy the outdoors.

You'll find tons of Maui cruisers on craigslist if you're looking to get a car. Those are the used cars that still get you from A to B, even if they aren't as nice as new car or a used one for a dealership. 

There usually pops a car you can buy for around $1000 on craigslist or facebook marketplace if you look long enough. Those are good if you know your way around a car and an engine. You might even be able to find one that has some issues, fix it up and then repost it. 

Maui is such a transient place that there will always be people looking for a car.

If you don't know how to fix cars, you usually won't find anything other than a work-in-progress for less than $1500, but if you want to be on the safe side, go for $2500 or more. As long as you don't wreck it, you'll always be able to sell it to recoup your costs (at least some, if not more) and you'll have a more reliable ride to get you to where you want to go.

Other ways to save money

Island Life is expensive but there are a handful of ways that you can save money. Costco, Househacking, Car hacking, thrift shopping, and Grocery Store apps are just a few ways you can pinch a penny.

While not something you would have to do in the ideal world, if it helps you live in paradise, why not change up the lifestyle to help you smile every day?

How can I stay fit and healthy? Gym or outdoors?

Most of the appeals to moving to Maui include being outdoors in one way or another. It's easier to be motivated to go outside when you're somewhere as beautiful as Maui and there are unlimited opportunities to enjoy the outdoors on Maui. 

Whether it's being on the water, surfing, paddleboarding, kayaking or just swimming to hiking through the jungle to hiking up part of Haleakala and launching with your paragliding wing back down to your car, Maui is one of the active places that inspires you to get up and go play in the outdoors.

Why to Move to Hawaii?

Weather, sunshine, water, outdoors, aloha

Outdoor sports

water sports

Why Should I NOT Move to Hawaii?

Family, Cost of Living, an indoor lifestyle, to live on the beach

Ways to keep busy and hobbies

Water sports

Other ways to make money

Air travel

Time of Year

Quality of Life


What Can I do for work? What's the best job for me in Hawaii?


You have to find a way to support yourself on the island. When I first moved to Maui, I was really lucky.

Everything fell into my lap. I was offered a job on a boat, where I worked for four years. It ran nightly and I saved a lot of money eating the catered food that wasn't ordered. They didn't use the food cooked for a trip the next day, so the crew on the boat ate to their heart's content because whatever was left over had to go in the trash.

Needless to say, Tourism and Hospitality are industries on Maui and in Hawaii. People are always visiting from all over the world, no matter the time of the year. Just like San Fransisco is home to Silicon Valley and a huge tech hub, Hawaii and Maui are Tourism hot spots.

Resorts, restaurants, boating charters and activity trips like zip-lining and horse-back riding are constantly in demand on the islands. There are always jobs available working these positions, regardless of the time of year. 

The boating industry gets busier too during whale season, when the humpback whales come down to the islands during the winter months.

[Tourism Data]

One way to get your foot in the door when moving to Hawaii if you don't have a set career is to find a job that gives you other benefits as well. 

In my example, I worked on a boat that had a surplus of food, so I didn't have to buy dinner every night. Where a lot of people end up losing money when moving to Hawaii, I was able to save because I didn't have to buy dinner every night.






Word of Mouth


Lifestyle Jobs

Boats, Guides, Musician, Artist






Life Hacking


Digital Marketing



Little Time Investment For Extra Side Cash


More Investment, More Reward


How can I get around? Car, Scooters and Transportation


Where Will I live? Housing on the Islands


Word of Mouth


Air Travel and Flights



Flight attendants

Time of Year


Whale Season

Quality of Life






Money-saving Tips




Island Life





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How to Move to Maui
Job and Finances
Multiple Jobs?
Work Remotely? Online Jobs
Digital Marketing
Social Media Marketing
Job with Benefits
Places to Live
Areas of the Island
One month
Six Month
One Year
Two Year
Four Year
Facebook Marketplace
Save Money
Savers / Thrift Stores
Quality of Life
Health and Exercise
Work to Live or Live to Work?
Bare Necessities