Signs It Might Be Time to Leave Hawaii

Written by a couple who've made this move both directions.

Making the choice to leave Hawaii was not an easy one. We had to consider so many things. Of course the obvious: we’d be leaving the beauty of the island such as the beaches and nature. We’d be leaving the friends we’ve made behind (that was really hard). However, the signs it’s time to leave Hawaii were there for us.

One the flip side, we chose to leave the island for many reasons including the cost of living (rent and groceries), missing our families, the cost of flying to and from the continent, and believe it or not–noise pollution (more on that later).

I’ll share some real, practical, and emotional signs that it might be time to leave Hawaii.

How do I know it’s time to leave Hawaii?

You’ll likely know that it’s time to leave Hawaii when you are constantly thinking and talking about making the move. Maybe you’ve been brainstorming places to move or have even checked out some moving companies. If the desire is there and you’re feeling it strongly, it is a strong sign that it’s time to leave.

Key Takeaways

• The cost of living, especially for groceries, rent, and gas, was one of the biggest reasons for us wanting to leave Hawaii
• Missing major family events and the high cost of flights to visit family became a real financial strain
• “Island fever” began creeping in. What used to be exciting turned into restlessness and boredom by year three.
• Housing was permanently out of reach on Oahu. The HOA fees alone ($1,000/month or more) and rent for a small apartment being equivalent to a larger home in another state
• The desire to leave is a consistent feeling. It builds over time due to financial and emotional factors.

Why This Decision Is So Hard to Make

Hawaii is a hard place to leave. Living there is not always paradise but there are so many things to enjoy on the island. For one, the weather is great if you don’t mind some humidity. The cooler season is wonderful. Plus, the friends that we made and people that we met made living there enjoyable.

Besides that, we worked hard to move to Hawaii. We made the decision and took the steps to make it happen. It cost us not only financially but emotionally because we were leaving family behind. And of course, leaving a place that many people would love to live or even visit.

10 Signs It Might Be Time to Leave Hawaii

The following are some signs that we either experienced or watching others go through when deciding to leave the island.

1. The Cost of Living Is Outpacing Your Income

It’s not a secret that the cost of living is high in Hawaii. Not being able to keep up with the cost of living is one of the number one signs it’s time to leave Hawaii. The high cost of groceries, gas, rent, and dining out are some of the reasons we chose to relocate.

For us, the groceries were eating up a lot of our budget. After living on Oahu for 4 years, the grocery prices here on the continent gave us reverse sticker shock. A dozen eggs on Oahu averaged between $8 – $10. On the continent, we can get a dozen eggs for less than $2 at some supermarkets. We tried to save money by shopping at Costco but our tiny apartment didn’t offer room for bulk items. That meant having to shop at Foodland, Times, or Safeway on many occasions.

2. Your Career Has Hit a Ceiling

Depending on your career field, you may find that it is difficult to move up or you may have moved to Hawaii and realized later that the industries are limited with fewer senior roles or lower pay. The opposite actually happened in our case. My wife’s career actually took off after moving to Oahu because of her career field. However, the pay was still lower for something comparable on the continent.

3. You’re Missing Major Milestones With Family on the Mainland

This was also a major reason why we moved from Hawaii. We began to miss so much time and major events with our family. The cost of flights made it difficult to visit family as often as we would’ve liked. We actually ended up in debt because of family emergencies and flying back and forth.

4. “Island Fever” Has Become a Regular Feeling, Not a Phase

I honestly didn’t think that I would experience island fever. If you’re not familiar with the term, island fever is a feeling of isolation, claustrophobia, boredom, and restlessness that tends to happen living in an isolated area like an island. Initially, it was fun and exciting because everything was new to us.

After a couple of years of living on Oahu, island fever began to set in for me. We did most of the major events. There was nowhere “new” to go. Leaving the island to fly someplace else was costly. By year three, I was over it. I was ready to go and so was my wife. We began to speak more about moving more often.

5. Housing Feels Permanently Out of Reach

If you watch videos on YouTube created by Hawaii real estate agents, you will think that buying a home in Hawaii is attainable. The truth of the matter is that almost any house on the island of Oahu is almost always over $1 million dollars. Condos may be more affordable but not by much when you take maintenance fees and HOA fees into account.

Some HOA fees are well over $1,000 a month for many condominiums. Renting isn’t much better. Many apartments will be around $2,500 – $3,500 or more a month. What you pay in rent for a one bedroom apartment or studio, you can rent a 2-3 bedroom home in another state like Texas or Nevada.

For us, we never considered buying a home or condo on Oahu. The HOA fees alone were too much to consider any of it. Now that we’ve relocated, buying a home feels much more attainable. Note: we now rent a two-bedroom, two-bath home with central air for the same amount of rent we paid for a one-bedroom apartment in Honolulu with no windows (only jalousie windows) and no AC.

6. Your Health (Physical or Mental) Needs Resources Hawaii Doesn’t Have

We didn’t experience this personally, but it is a real issue for many people living in Hawaii. Appointments for specialists could be months out or the specialist you need is not available on the island. If this is an issue you’re dealing with, it is a huge sign that it’s time to consider relocating if it is possible.

7. You’re Constantly Trading Necessities for the “View”

There are so many beautiful spots on Oahu and for many people, that’s what keeps them living there. I loved that we lived 10 minutes from Ala Moana Beach Park. It was my favorite beach park and one that I miss. However, it was not enough to want to continue living on Oahu. The grocery prices were a burden for us and so was our living situation. We lived in a 3-story walk-up which was a hassle when carrying heavy grocers or laundry up and down the stairs.

8. Your Support System Has Thinned Out

I’m an introvert so this doesn’t apply to me as much as it may for someone who likes to make new friends and have a support system. For some, it is challenging to build a lasting community as many people they form relationships with may leave the island for their own reasons. There is a big difference between simply having neighbors and having real support.

9. You Feel Guilty for Wanting to Leave and That Guilt Is Wearing on You

I can imagine feeling guilty for wanting to leave may happen for people who leave behind family on the island. Or maybe you were born and raised in Hawaii or lived on the island for decades. Whatever guilt you feel doesn’t mean having the desire to leave is wrong.

10. You’ve Started Researching Moving Companies “Just to Look”

One of the sure signs it’s time to leave Hawaii is when you begin checking out moving companies and figuring out logistics to move simply out of curiosity. That curiosity is stemming from a deep desire that is worth paying attention to. It started for us when we began brainstorming other states we would want to move to.

Signs It’s Not Time to Leave (Yet)

Now, for as many signs it’s time to leave Hawaii, there are many for signs it’s not time to leave. For example, if you’ve experienced a bit of a financial dip, it doesn’t mean it’s time to pack up and leave as long as the dip is temporary. Homesickness is often a reason to want to leave. If it’s only occasional versus constant, leaving doesn’t need to feel like a priority.

How to Know for Sure: A Quick Self-Check

A good self-check as to whether you truly want to leave Hawaii is to ask yourself some questions. Good questions to ask yourself include:

• Has the feeling of wanting to leave lasted more than a year?
• Would having more money keep you from wanting to move off the island?

Also read: Shipping a Car & Household Goods From Hawaii

What to Do Once You’ve Decided

If you’ve finally decided that you want to leave Hawaii, that is only the first step. There is the practical side of things to consider next such as saving for your more, shipping your belongings, timing your move, or even deciding where you want to move to.

The different signs listed on this post are significant but on their own, they do not mean you have to pack up everything and move tomorrow. Below is a table to help you tell the difference between a passing rough patch and an actual sign that you’re ready to go:

Sign It’s Time to Leave	Sign It’s Not Time to Leave
Cost of living has outpaced your income for over a year	You had one unusually expensive month or season
You feel constant, low-grade island fever	You’re just missing a specific holiday or event back home
Your career has genuinely plateaued with no path forward	You had one rough year at work, but growth is still possible
Housing feels permanently out of reach on your income	You’re saving toward a home, just not there yet
You feel guilty for wanting to leave, and it’s wearing on you	You’re second-guessing a single hard week, not a pattern

Frequently Asked Questions

Final Thoughts

Leaving Hawaii has been a positive experience for us. While we enjoyed parts of living there, we feel that our quality of life has improved significantly. We have a larger place to live, grocery prices are extremely reasonable in comparison to Oahu, and we have more options in terms of shopping in general.

Making the decision to leave Hawaii wasn’t one that we took lightly. We talked about it for awhile and even wrote out a checklist of what we needed to do to make it happen. Whatever you decide, it will be the right decision for you.