Aloha! If you’re thinking about retiring in Hawaii, let me be the first to say: great choice. Living here is like being on a never-ending vacation—stunning beaches, warm breezes, and a relaxed island lifestyle. But before you sell everything and hop on a plane, there are a few things you should know. While Hawaii is paradise, it’s not for everyone. The cost of living is high, and finding the right community can make all the difference in whether you truly enjoy your retirement years.
As someone who lives here, I’ve learned a few things about Hawaii, and I want to help you make the best decision. Let’s break down the top places in Hawaii to retire, what to consider before making the move, and some insider tips to help you transition smoothly.
What Makes Hawaii a Great Place to Retire?
So, why do so many people dream about retiring in Hawaii? Well, let’s start with the obvious:
- The Weather – No snow, no extreme temperatures—just sunshine, ocean breezes, and mild temperatures year-round. You can leave the winter coats behind! Or, most of your wardrobe for that matter.
- The Lifestyle – Hawaii runs on “island time.” That means a slower, more relaxed pace of life, perfect for retirees who want to take it easy.
- Natural Beauty – Whether you love hiking, snorkeling, or just sipping coffee while watching the waves, there’s no shortage of breathtaking scenery.
- Healthcare Access – While the islands are remote, we have world-class hospitals and medical centers, especially on Oahu.
- Diverse Community – Hawaii has a rich mix of cultures, and locals are known for their warm, welcoming nature.
Of course, there are challenges too, like high costs and being far from family on the mainland. But if you can make it work, retiring here is pretty hard to beat.
Key Factors to Consider When Retiring in Hawaii
Before picking out a beach house, let’s talk about some real-life considerations:
1. Cost of Living
Hawaii isn’t cheap. Groceries, housing, and even gas cost more than on the mainland. Significantly more. That said, some areas are more affordable than others (I’ll get into that later). If you’re on a fixed income, you’ll want to budget carefully.
2. Healthcare Access
Oahu has the best hospitals and medical facilities, but if you’re considering Maui, the Big Island, or Kauai, check how close you’ll be to doctors and emergency care. Some insurance plans cover travel from the outer islands to Oahu for care. Check your coverage.
3. Community & Lifestyle
Some retirees want the convenience of city life in Honolulu, while others prefer a quieter, rural vibe. Hawaii has options for both, but it’s important to know what kind of lifestyle you want.
4. Family & Travel
Hawaii is far from the mainland. If you have family on the West Coast, visits are manageable, but if they’re on the East Coast, flights can be long and expensive.
With these things in mind, let’s dive into the best places to retire in Hawaii.
Top Retirement-Friendly Communities in Hawaii
Hawaii isn’t one-size-fits-all when it comes to retirement. Some people want to be close to world-class healthcare and shopping, while others just want to live quietly by the beach. I’ve put together a list of the best places to retire, each with its own unique charm.
Honolulu, Oahu – Urban Convenience with Island Charm
0704Hawaii037 by Luke H. Gordon is licensed under CC BY 2.0. Image may have been resized or cropped from original
The view of Diamond Head from anywhere is majestic, but the brown lava contrasts with the blue of Waikiki’s Pacific Ocean so beautifully.
If you love the idea of retiring in paradise but still want the perks of city life, Honolulu is your best bet. It’s the largest city in Hawaii, home to the best hospitals (like The Queen’s Medical Center), major shopping centers, and plenty of entertainment.
Pros:
✔️ Top-tier healthcare facilities
✔️ Plenty of senior-friendly activities (museums, parks, beach walks)
✔️ Public transportation makes it easy to get around
Cons:
❌ High cost of living (especially in Waikiki)
❌ Busy traffic in some areas
If you want a quieter lifestyle but still need access to city amenities, check out the neighborhoods of Hawaii Kai or Kailua. They offer beautiful scenery without the hustle and bustle of downtown Honolulu.
Hilo, Big Island – Affordable and Laid-Back Living
Stunning photo of “Coconut Island” in the town of Hilo, Hawaii. source: https://pixabay.com/en/coconut-island-hilo-hawaii-palm-1975480/ Pixabay image. No attribution required.
Hilo is the opposite of Honolulu—it’s peaceful, lush, and much more affordable. Located on the east side of the Big Island, Hilo is a retiree’s dream if you love nature, waterfalls, and a strong sense of community.
Pros:
✔️ More affordable housing options compared to other islands
✔️ A slower, relaxed lifestyle—no tourist crowds
✔️ Beautiful rainforests and waterfalls to explore
Cons:
❌ More rain than other parts of Hawaii (if you love sunshine, this might not be for you)
❌ Fewer medical facilities compared to Oahu
Hilo is perfect for retirees who don’t mind a little rain in exchange for a quiet, nature-filled lifestyle.
Kailua-Kona, Big Island – Sunny and Beachside Living
If you love sunshine, head over to the other side of the Big Island—Kailua-Kona. Unlike Hilo, this area is warm and dry, with some of the best beaches on the island. It’s great for active retirees who enjoy snorkeling, fishing, or golfing.
Pros:
✔️ Gorgeous weather year-round
✔️ Plenty of outdoor activities and a laid-back vibe
✔️ Lower cost of living than Oahu or Maui
Cons:
❌ Fewer hospitals (though there are good clinics and urgent care centers)
❌ Some areas can be tourist-heavy
Kailua-Kona is a great middle ground—relaxed but still lively enough to keep you entertained.
Kahului, Maui – Ideal for Nature Lovers
Maui is a favorite for retirees, and Kahului is a good mix of convenience and affordability (by Maui standards). It’s not as touristy as Lahaina or Kihei, but it still offers beautiful beaches, shopping, and good healthcare options.
Pros:
✔️ Central location with easy access to medical care
✔️ Great for outdoor lovers—hiking, beaches, waterfalls
✔️ Less crowded than other Maui spots
Cons:
❌ Still more expensive than the Big Island
❌ Limited public transportation
If you’re looking for a mix of adventure and relaxation, Maui might be the perfect fit.
Kihei, Maui – Beachside Retirement Haven
Kihei is on Maui’s south side and is one of the sunniest spots in Hawaii. It’s got a real community feel, with farmers’ markets, local restaurants, and easy beach access.
Pros:
✔️ Warm, dry weather—perfect for beach lovers
✔️ Friendly, close-knit community
✔️ Plenty of condos and senior-friendly housing options
Cons:
❌ Still pricey, though cheaper than luxury areas like Wailea
❌ Can get busy with tourists
For retirees looking for that classic island lifestyle, Kihei is a solid choice.
Princeville, Kauai – Luxurious Retirement Destination
If money isn’t a concern and you want to wake up to some of the most stunning views in Hawaii, Princeville on Kauai’s north shore is breathtaking. It’s an upscale community with golf courses, high-end homes, and a peaceful vibe.
Pros:
✔️ Gorgeous mountain and ocean views
✔️ Exclusive, quiet community
✔️ Excellent golf courses and resort-style amenities
Cons:
❌ High cost of living
❌ Limited medical facilities nearby
If you want to retire in luxury, Princeville is as good as it gets.
Lihue, Kauai – Small-Town Feel with Modern Amenities
Lihue is the main hub of Kauai, so it has more modern conveniences while still maintaining that small-town charm. It’s perfect for retirees who want a relaxed lifestyle but still need access to good healthcare and shopping.
Pros:
✔️ Centrally located with good healthcare access
✔️ Less expensive than Princeville or Poipu
✔️ Close to beaches, shops, and restaurants
Cons:
❌ Not as remote and quiet as other Kauai areas
❌ Still pricey compared to mainland cities
Lihue is a great balance of affordability (by Hawaii standards) and convenience.
Cost of Living and Affordability in Hawaii for Retirees
Let’s talk money—because Hawaii isn’t exactly the cheapest place to live. But don’t let that scare you off just yet! With some planning, you can make it work.
- Housing Costs: A single-family home can easily top $1 million in places like Honolulu or Maui. But if you’re open to a condo or townhouse, there are more affordable options in areas like Hilo or Lihue.
- Utilities & Groceries: Expect to pay more for electricity, water, and groceries since nearly everything is shipped in from the mainland. Local farmers’ markets can help you save on fresh produce.
- Taxes: Hawaii is friendly to retirees when it comes to property tax (one of the lowest in the U.S.), but it does tax pensions and retirement income.
If cost is a big concern, Hilo, Kailua-Kona, and Lihue tend to offer more affordable living than Oahu or Maui.
Best Retirement Communities and 55+ Living Options
Not everyone wants to maintain a big house in retirement, and that’s where Hawaii’s retirement communities come in.
Some of the best include:
- Hawaii Kai Retirement Community (Oahu): Resort-style senior living with tons of amenities.
- Roselani Place (Maui): Assisted living and independent living options.
- Regency at Hualalai (Big Island): A mix of retirement apartments and assisted care.
If you prefer a condo over a full-blown retirement community, look for senior-friendly buildings with elevators, security, and easy beach access.
Healthcare and Senior Services in Hawaii
Good healthcare is a must in retirement, and Hawaii has excellent hospitals—especially on Oahu.
Best Hospitals for Retirees in Hawaii:
- The Queen’s Medical Center (Oahu): Best overall care in the state.
- Maui Memorial Medical Center: Largest hospital on Maui.
- Hilo Medical Center: Great for Big Island residents.
Smaller islands have clinics and urgent care centers, but if you need specialized treatment, you might have to fly to Oahu. Many retirees opt for Medicare Advantage plans that cover inter-island travel for medical needs.
Outdoor Activities and Lifestyle for Retirees
One thing’s for sure—retiring in Hawaii means staying active! There’s no shortage of things to do:
Beach Days: Lounge on the sands of Waikiki, Hapuna Beach, or Poipu.
⛳ Golfing: World-class courses in Princeville, Wailea, and Ko Olina.
Hiking: Enjoy scenic trails like Diamond Head, Manoa Falls, or Pololu Valley.
Fishing & Boating: Perfect for retirees who love the ocean.
Community Activities: Many towns have senior centers offering ukulele classes, hula lessons, and volunteer opportunities.
Challenges of Retiring in Hawaii
No place is perfect, and Hawaii does have its downsides. Here are the biggest challenges retirees face:
- High Cost of Living: Even with budgeting, things just cost more here.
- Island Fever: Some people feel isolated being so far from the mainland.
- Limited Medical Care in Some Areas: If you have serious health concerns, consider living near a major hospital.
- Natural Disasters: Hurricanes, tsunamis, and volcanic activity are rare but possible.
That said, if you can handle these challenges, Hawaii’s beauty and laid-back lifestyle make up for it.
Conclusion: Is Hawaii the Right Place for Your Retirement?
So, is retiring in Hawaii the dream life you’ve been looking for? If you love warm weather, the ocean, and a slower pace of life, it might just be paradise. But it’s important to pick the right island and community for your needs.
If you’re unsure, I always recommend renting for a year before committing. That way, you can experience daily life without diving in headfirst.
At the end of the day, Hawaii isn’t just a place—it’s a way of life. And if you’re ready to embrace it, retirement here can be truly magical.
FAQs
What is the most affordable place to retire in Hawaii?
Hilo on the Big Island is one of the most affordable options, with lower home prices and a lower cost of living than Honolulu or Maui.
Is healthcare in Hawaii good for retirees?
Yes, especially on Oahu, which has the best hospitals and specialists. Other islands have good healthcare, but for serious medical needs, you may need to travel to Oahu.
Are there tax benefits for retirees in Hawaii?
Hawaii has low property taxes, but it does tax pensions and retirement income. It’s a good idea to check with a tax advisor before moving.
What are the best senior-friendly activities in Hawaii?
Golf, hiking, fishing, beach days, and community events like farmers’ markets and cultural festivals are all popular with retirees.
How can I find affordable housing for retirement in Hawaii?
Consider looking at condos in Hilo, Lihue, or Kailua-Kona. Also, check for 55+ communities and senior housing programs.
What do you think?