Which Hawaiian 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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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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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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Due to the abundance of hotels, activities, tours, and attractions, Oahu is the cheapest Hawaiian island to visit. Between the competitive prices and myriad of things to do, those looking for a budget vacation to Hawaii will find that Oahu is exactly what they've been searching for.

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One of the greatest challenges of living in Hawaii is the high cost of living. The islands are popular tourist destinations, which drives up the cost of housing, food, and other essential goods and services.

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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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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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Among the Hawaiian Islands, Molokai is known as the Friendly Isle, and those who live there would consider it the best island to live on by far. With many longtime families and few visitors living on remote Molokai, it is one of the most secluded Hawaiian Islands.

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Molokai. The most local of the main Hawaiian Islands, Molokai also receives far fewer visitors than the other islands and will have the least touristy feel.

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Many retirees dream of retiring in Hawaii. The temperate climate and relaxing atmosphere of the islands may be the lifestyle reset retirees are seeking after decades of hard work. While retiring in Hawaii is generally quite expensive, for some retirees the move offers the opportunity to save money.

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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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Hawaii has a high cost of living. Pro: The mild climate makes Hawaii a year-round destination. Con: It can feel isolating living on an island if you don't embrace it. Pro: Moving to Hawaii is an adventure, and you'll be the envy of everyone you know if you take the dive and do it.

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In summary, Hawaii offers stunning natural beauty, a laid-back lifestyle and lower cost of living, while California boasts vibrant cities, a strong job market and excellent entertainment options. Consider your priorities – if you want island living, Hawaii may be your ideal match.

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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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Average Home Prices: The average median home price in Hawaii is $679,600, down by 9.07% YoY. In 2023, experts predict the median sale price growth to drop by roughly 4%, the first annual drop since 2012. Currently, the sale-to-list price ratio is at 98.1%, with a decline of 2.8 pt YoY as of April 2023.

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Downtown Honolulu, Ala Moana, Diamond Head, and Waikiki are all excellent examples. The bus routes in these areas stop at nearly every single block, and almost all properties will be directly on the bus line. You'll find that you can get anywhere on the island from a property in these areas.

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