Which Hawaii island is best to retire on?

Kaua?i now holds the #2 spot, followed by Maui, and then by O?ahu.
  • 1 - Big Island.
  • 2 - Kaua?i.
  • 4 - Oahu. (Source) In other words, if you plan to retire in Hawai?i, you'll find an increasing number of Hawai?i residents in your age group to mingle with—especially on the Big Island.




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Retirees who move to Hawaii also benefit from the Aloha State's lower health care costs, state-of-the-art medical system, and retiree-friendly tax laws. Social Security income and public pension withdrawals are not taxed for Hawaiian residents, leaving more money in your pocket.

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Most Affordable Places to Live in Hawaii
  • Hana, Maui.
  • Hilo, Island of Hawaii.
  • Kahuku, Oahu.
  • Kahului, Maui.
  • Kapa'a, Kauai.
  • Waianae, Oahu.
  • Wailuku, Maui.
  • Waimalu, Oahu.


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You'll need six figures per year to retire comfortably in Hawaii. Hawaii has the highest annual retirement expenses in the country, costing retirees an estimated $121,228 annually. It's also the only state or district where retirees need to spend six figures.

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Oahu is the driest out of the main Hawaiian islands when it comes to the weather. With the shining sun year-long most of the time, usually along the coast, you can't have a bad weather day.

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Kauai, known as the “Garden Isle,” has the lowest violent crime rate among the four major Hawaiian islands. Its smaller population and close-knit communities contribute to a sense of security and safety.

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What's the most affordable Hawaiian island to live on? The Big Island. With Hawaii's lowest average cost of living (according to MIT's Living Wage project), lowest fair market rents, and lowest typical yearly expenses, the Big Island can be the most economical island in Hawaii.

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With this in mind, the ideal times to move to Hawaii are between the months of January and May, or between the months of September and November. With fewer tourists in the area, you can find cheaper flights; finding a car rental and short term accommodations will be a lot easier.

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Let's take a look at the five safest neighborhoods and what makes them good places to live for you and your family.
  1. Kahala. One of Oahu's most prestigious neighborhoods is Kahala. ...
  2. Mililani. ...
  3. Hawaii Kai. ...
  4. Kailua. ...
  5. Manoa.


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Cost of Living The most obvious drawback to living in Hawaii is our cost of living. Because everything needs to be imported, the cost of goods is significantly higher than any mainland market.

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Of course, living in Hawaii also has its challenges. The cost of living can be high, especially in terms of housing and groceries. The islands are also isolated from the mainland, which can make it difficult to access certain goods and services.

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Niihau, also known as the Forbidden Isle, is a beautiful small island in Hawaii spread across 180 sq km. The island is off-limits to outsiders and only the Robinson family, their relatives, invited guests, government officials and US Navy personnel are allowed here.

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Using data from The Hawaii Tourism Authority and Kayak.com, the cheapest island to visit is Oahu. Airfare, hotel, and rental car for two people for a week costs $2,625 on Oahu. The most expensive Hawaiian island to visit is Maui, where the same average costs for a week are $3,600.

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Dominican Republic, Belize (the only English-speaking country in Central America), Costa Rica, and Panama are a few of the most affordable islands to live on and double up as top destinations to visit.

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Lanai entices the sophisticated traveller with a handful of exclusive luxury resorts and championship golf courses. It's the least visited Hawaiian Island, small in size and slow in pace those that travel to Lanai, by air or on the ferry from Maui, are forced to rest and relax.

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The best time to visit this Hawaiian island to avoid tourist crowds is April to June and September to November. Lanai and Molokai are the least visited islands and are the perfect rural getaways for introverts.

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To live comfortably in Hawaii, an annual income of around $70,000 to $100,000 for a single person, or $120,000 to $200,000 for a family is recommended. Is it expensive to live in Hawaii? Yes, Hawaii is known for its high cost of living due to factors such as housing, groceries, utilities, and transportation.

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