How To Retire In Hawaii From Canada: 6 Steps to a Tropical Paradise (2024)

Looking to retire in a tropical paradise?

Even though Hawaii seems like a world apart from the rest of the North American continent, it’s technically a part of the United States, which means that Canadians can stay in the country for six months out of the year without having to apply for a Visa.

Alternatively, Canadians can apply for a residency Visa to retire in Hawaii full-time.

Below, I’ll explain how to retire in Hawaii from Canada, following these steps:

  1. Deciding on snowbird vs full-time retirement
  2. Research and apply for a US Visa
  3. Decide which Hawaiian island you want to live on
  4. Plan your retirement income and budget
  5. Plan your living situation
  6. Transport your belongings to Hawaii

Are you ready to travel to the land of surf and sunshine?

Does Hawaii Offer Retirement Visas To Canadians?

Retirement Visas are special long-stay Visas that are issued to foreigners looking to retire outside of their home country. To be approved for a retirement Visa, the applicant typically needs to show that they have

  • Steady, reliable retirement income
  • Adequate healthcare coverage
  • A place to live

Many countries, such as Thailand, offer these Visas to ex-pats.

Retirees get to take advantage of the lower cost of living in other countries and spend their golden years exploring an exciting new country, and retirees spend money in the country and contribute to the local economy. It’s a win-win situation for both parties.

Hawaii is a US state, and the US doesn’t offer retirement Visas to foreigners.

However, all Canadians with a clean criminal record and a valid passport may stay in the US for six months (180 days) during a calendar year. This means that you could potentially retire in Hawaii for half of the year and return to Canada to spend time with friends and family for the remaining half of the year.

The stay doesn’t have to be for exactly six months either. For example, you could stay for four months, return home to Canada, and then return for another two months during the same year. It’s all up to you!

How To Retire In Hawaii From Canada: Step-by-Step

Ready to start planning your retirement? Retiring overseas may seem complicated at first. If you break it down into steps, though, you can create an action plan and retire in Hawaii in a year (or less).

Let’s get started, shall we?

Step 1: Snowbird Retirement vs Full-Time Retirement

Step 1: Snowbird Retirement vs Full-Time Retirement

Since the US (and, by extension, Hawaii) doesn’t offer full-time retirement Visas to Canadians, you’ll need to choose between two different retirement paths:

  • “Snowbird” retirement (staying in Hawaii/the US for six months a year)
  • Full-time retirement (apply for a Green card and permanent residency in the US)

As I mentioned above, snowbird retirement is the easiest way to retire in Hawaii as a Canadian. Some of the benefits to this retirement path include:

  • No Visa application process, paperwork, or fees
  • You can stay for up to six months a year, on your own schedule, with unlimited travel to and from Canada
  • You can purchase or rent property in Hawaii, even if you’re a foreigner
  • You don’t have to leave your life in Canada behind completely
  • You’ll still be eligible for most of your Canadian benefits and government pension payments

Of course, the main downside of snowbird retirement is that you must return to Canada for the other half of the year. This can involve extra planning and requires you to purchase plane tickets (which can be expensive).

It also means you’ll need to maintain a secondary residence in Canada unless you plan on renting or staying with family when you return.

Step 2: Research Your US Visa Options

Step 2: Research Your US Visa Options

Although the US is very generous to Canadian visitors and snowbird retirees, the country also makes it very difficult to obtain a Green Card or Visa for full-time residency.

Many countries (like Italy) allow foreigners to obtain a long-stay Visa, which can eventually transfer into full-time residency after you’ve spent enough time there.

In the US, your Visa options are far more limited. Realistically, you won’t even be able to apply for a Visa unless:

  • You have family members in the US who have Green Cards or are citizens
  • You purchase or start a business with an investment of over $1.8 million USD

Here’s a quick table outlining the different ways that Canadians can obtain a US Visa and full-time residency:

Green Card PathDescription
Family sponsorshipIf you have a spouse or family member with a Green Card or a US citizen, they can “sponsor” you and help you apply for your green card.
Investment green cardIf you invest in a US-based business (with an ownership percentage) or start a business in the US that meets certain employment requirements, you may be issued a green card.
Employer sponsorshipIf you have an employer in the US, they can “sponsor” you to obtain a work-based Green Card. This defeats the point of retirement, though.
Diversity LotteryA small percentage of green card applicants with a historically low rate of immigration may be given a residency Visa. These are very rare, though, and are issued based on “the luck of the draw.”
Refugee or asylum green cardIf you’re a refugee or seeking political asylum, you may be issued a Green Card. This doesn’t apply to most Canadian retirees, though.

The fastest way to obtain a US Green Card is if you get married to a US citizen or have extended family living in the US. For example, many Canadian parents have children who went to school in the US, obtained a US work Visa, and then went on to pursue a Green Card or citizenship.

If money isn’t an issue, then you may consider the investment Visa option. There are two paths here:

  • Purchase an ownership percentage in an existing business
  • Start your own company

To qualify for an investor Visa, though, you must invest at least $1.8 million USD ($2,429,703.00 CAD).

The company you purchase or start must also employ people, meaning you can’t just buy an apartment and rent it out as a business.

If you’re trying to retire and enjoy the rest of your life in peace, this may not be the best option for you.

However, if you do go down this route, I’d suggest the first option.

If you do your research, you may be able to purchase an existing business that’s already successful and doesn’t require as much personal involvement on your end. Examples of this could include:

  • A restaurant or franchise location
  • A small hotel with full-time staff
  • A gas station
  • A home services company

You’d want to select a business with a proven track record and good management. While you would technically be the owner, you should be able to spend your time as you please, while your managers, accountants, and attorneys care for the business.

That being said, the risk is that the company goes under, and you lose a lot of money.

Step 3: Decide Which Island You Want To Live On

Step 3: Decide Which Island You Want To Live On

After deciding the residency option that best suits your retirement lifestyle, you’ll need to decide which island you want to live on.

The state of Hawaii consists of seven islands:

  • Hawaii (the Big Island): The largest and youngest of the Hawaiian islands is home to two active volcanoes, Mauna Loa and Kilauea.
  • Oahu: The “Gathering Place” is home to the state capital of Honolulu and the iconic Waikiki Beach.
  • Niihau: The “Forbidden Island” is the most isolated and privately owned island in the Hawaiian chain.
  • Kauai: The “Garden Island” is the oldest and most lush of the Hawaiian islands.
  • Molokai: The “Friendly Isle” is known for its beautiful beaches, waterfalls, and Kalaupapa National Historical Park.
  • Lanai: The “Pineapple Island” is a popular destination for luxury resorts and outdoor activities.
  • Maui: The “Valley Isle” is home to Haleakala National Park, the Road to Hana, and the famous Lahaina Plantation.

Interestingly, Hawaii’s main capital city, Honolulu, and most of its population don’t live on the “Big Island” of Hawaii, which is mostly a rural farming island. Instead, most of the state’s population lives on Oahu, which is a mid-size island and home to the capital.

Oahu is where you’ll find most of your creature comforts, such as Walmarts, banks, fine dining, luxury hotels and shopping, car dealerships, resorts, nightlife, etc.

The other islands have a more rural feel. Housing tends to be older, and they’re more known for their resorts, natural beauty, and indigenous history.

Most retirees plan to retire on Oahu, as it’s more convenient. Healthcare, groceries, and shopping are more accessible. You can take a short 15-minute flight or ferry across the ocean to the other islands, though, which is a great way to spend a weekend exploring.

Step 4: Plan Your Retirement Budget And Income

Step 4: Plan Your Retirement Budget And Income

After figuring out where you want to retire, it’s time to start budgeting. Unfortunately, Hawaii can be a very expensive place to live. For reference, it’s one of the most expensive places to live in the United States.

The average rental rates and housing costs are similar to what you’d pay living in Toronto or Vancouver.

If you plan on retiring in Hawaii, you’ll need to have a reliable source of retirement income that exceeds what you’ll get from the federal Old Age Security (OAS) and the Canada Pension Plan (CPP) programs.

A recent study indicated that the average person would need an annual salary of at least $200,000 USD ($269,967 CAD) to afford the cost of living in Hawaii to be “happy”.

You can live for much less than this amount as the average salary in Hawaii was only $72,000 USD, but the study was an interesting read and detailed many of the costs you can expect to have.

Of course, you could also compensate for this with passive retirement income, such as that earned from owning rental properties, stock dividends, investment portfolios, and more.

Step 5: Plan Your Housing Situation

Step 5: Plan Your Housing Situation

If you’re planning on obtaining a full-time US Green Card, then you’ll likely want to purchase a home in Hawaii, as rental rates are incredibly high.

If you’re following the snowbird retirement path, you must account for splitting time between Canada and Hawaii.

In my opinion, the most straightforward path for this is to keep your home in Canada, purchase a second home in Hawaii, and rent your home out on AirBnB or VRBO while you’re out of the country.

If you play your cards right, the income from renting one house out for half of the year will be able to fund the mortgage on the second home you purchased.

Before travelling back home, simply store your personal/private belongings in a storage unit, allowing guests to take advantage of your furniture, dishes, TV etc.

To simplify things, just hire a property manager to take care of the property and manage guests, cleaning, and maintenance.

Step 6: Move Your Belongings And Fly Out

Step 6: Move Your Belongings And Fly Out

Finally, you’ll need to move your belongings and fly out to Hawaii. Since Hawaii is a rather remote island, you’ll likely need to pay for freight shipping if you plan on shipping out your car, furniture, or other bulky belongings.

To limit costs, I’d recommend leaving as many belongings as possible in Canada. It could easily cost thousands of dollars to ship all of your belongings overseas, which could be used to purchase new furniture or put towards a new vehicle in Hawaii.

FAQs About Retiring In Hawaii

To wrap up, here are a few quick-fire answers to some of the most frequently asked questions about retiring in Hawaii from Canada.

How Often Can I Stay In The US Without A Visa?

Without a US Visa or Green Card, Canadians can stay in the US for six months in a calendar year. The stay does not have to be consecutive and can be broken up into several trips if you wish.

Can I Use My Canadian Healthcare In Hawaii?

Unfortunately, Canadian universal healthcare won’t provide coverage if you travel or live outside Canada. You may be able to purchase travel healthcare through your provincial government. However, your best bet is to purchase a private health insurance plan to cover you while you’re in Hawaii.

What’s The Best Time Of Year To Live In Hawaii?

The best time of year to live in Hawaii is between December and March, during the peak of winter. The temperature and humidity levels are very high in the summer and can become unbearable if you’re used to a cooler climate.

Luckily, this also correlates with the frigid Canadian winters.

If you’re a snowbird retiree, you can escape Canada’s winter storms in Hawaii, when the islands have incredible weather. Then, you can return to Canada and enjoy its mild summers, avoiding the peak of tropical heat in Hawaii.

Conclusion – Hawaii Is Expensive But Incredible

Hawaii is an incredibly beautiful place to live and retire in. However, the cost of living is very high, and you’ll need a high retirement income to live comfortably.

The good news is that you can stay in Hawaii for up to six months out of each year without having to apply for Visa or uproot your entire life.

One of the best ways to develop steady retirement income is to invest in stocks and ETFs that offer reliable dividend payouts. Keep reading to see my list of the best dividend ETFs in Canada next!

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Author Bio - Christopher Liew is a CFA Charterholder with 11 years of finance experience and the creator of Read about how he quit his 6-figure salary career to travel the world here.

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2 thoughts on “How To Retire In Hawaii From Canada: 6 Steps to a Tropical Paradise (2024)”

  1. I lived there for 4 years (2017-2021). It is outrageously expensive to live on Oahu. Our rent was just over $6,000 (Can) per month and it was not a fancy place. Crime and homelessness is rampant on the island. The locals have to work 2-3 jobs in order to get by. Generations live in the same house, that is why you will see 6-7 cars outside of a home, its not a party going on, there are between 15-25 people living in a single house! Don’t get me wrong there are places on the Island that are indeed paradise and its a great place to visit but I sure would not want to live there no matter how good the weather is! There are no ferries between the islands, only a cruise ship and flights to get to the other islands. One goes shack happy after a year, the island is only 30×40 miles, so after a year of exploring you have seen everything multiple times and anything good is overrun with tourists! It was great during covid and the people got their island back for a year! People always ask us why didn’t we stay and retire there, its simply way to expensive and way too far away from anything else, literally in the middle of the pacific.


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