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Hawaii’s 11 Best Retirement Towns Ranked

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Hawaii’s 11 Best Retirement Towns Ranked


Hawaii is home to a wide range of towns that give older adults relaxing ways to enjoy their retirement years. Across the islands, retirees can find communities with easy access to healthcare and outdoor recreation. Coastal towns like Kailua-Kona and Līhuʻe offer ocean views and nearby medical care. Inland communities such as Waimea and Makawao provide cooler weather and an easier rhythm. Retirees may be drawn to smaller places with a strong community feel, while those wanting more services may prefer regional hubs like Hilo. Together, these Hawaiian towns offer a mix of natural beauty and everyday comforts.

Kailua-Kona

Keauhou Bay, Kailua-Kona, Hawaii.

Kailua-Kona is a coastal town on the Big Island of Hawaii with fewer than 25,000 residents. It continues to attract retirees thanks to its warm weather and ocean access. Areas like Kealakehe and Holualoa are still growing, with new subdivisions adding more housing options for people who want to stay long-term.

Most medical care is provided by the nearby Kona Community Hospital, and clinics throughout the Kona district offer additional services. Some of the main landmarks are Kailua Pier, Huliheʻe Palace, Kamakahonu Beach, and Kona Commons Shopping Center. These spots help residents stay active year-round.

Hilo

Overlooking Hilo, Hawaii.
Overlooking Hilo, Hawaii.

Hilo is a well-known retirement-friendly community on Hawaii Island, known for being easy to walk around. With about 48,000 residents, according to recent Census data, Hilo is a regional center for healthcare, education, and government services, which helps create long-term stability for residents.

Hilo Benioff Medical Center is the main hospital for East Hawaii and provides most of the area’s healthcare. There are also outpatient and senior care services, such as the nearby Life Care Center of Hilo.

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People in Hilo often spend time at places like Wailoa River State Recreation Area, Hilo Farmers Market, Liliʻuokalani Gardens, and Rainbow Falls. These spots are close to neighborhoods like Waiākea and Keaukaha.

Waimea

Rolling green pastureland with white fences near Waimea, Hawaiis Big Island.
Rolling green pastureland with white fences near Waimea, Hawaii’s Big Island.

Waimea is a small inland town on Hawaii Island with fewer than 10,000 residents. Because it sits at a higher elevation, the weather is cooler, with daytime temperatures usually between 70 and 80°F and nights that feel much cooler.

Residents have access to healthcare through local clinics and services linked to Queen’s North Hawai’i Community Hospital in Waimea, which provides essential care for the area. The town has strong connections to Parker Ranch, one of the country’s largest ranches, as well as nearby ranchlands. Waimea attracts retirees who want a quieter inland setting, strong community organizations, and fewer people.

Līhuʻe

A couple walks along Kalapaki Beach in Lihue, Kaua'i, Hawai'i
A couple walks along Kalapaki Beach in Lihue, Kaua’i, Hawai’i.

Līhuʻe serves as Kauai’s administrative and service center and has fewer than 10,000 residents. The town plays a central role in healthcare and government operations across the island. It is just 30 minutes from Hanapepe and offers retirees a small-town feel, with natural scenery all around.

Wilcox Medical Center is the largest hospital on the island and provides care for residents throughout Kauai. Notable landmarks include Kalapaki Beach, Nawiliwili Harbor, Kauai Museum, and Kilohana Plantation. Together, these sites support recreation, tourism, and community events across the area.

Kapa’a

Shops in downtown Kapa'a in Hawaii.
Shops in downtown Kapa’a in Hawaii. Image credit bluestork via Shutterstock.com

Kapaʻa sits on the east side of Kauai and has about 11,000 residents. It is easy to get around on foot, with everything you could need close by. The town serves as both a place to live and a hub for businesses in the area.

Residents can access healthcare at local clinics such as The Clinic at Kapaa or at Wilcox Medical Center in Līhuʻe. Some well-known spots in Kapaʻa are Kapaʻa Beach Park, the Sleeping Giant Trail, Coconut Marketplace, and Wailua River State Park. Coconut Marketplace has a Farmer’s Market twice a week, plus live local music. Hula classes and shows are also a local favorite offered at Coconut Marketplace.

Kailua

Overlooking Kailua, Oahu.
Overlooking Kailua, Oahu.

Kailua is a residential area on the windward side of Oahu with fewer than 50,000 residents. The town is known for its easy access to beaches and well-established neighborhoods such as Enchanted Lake and Coconut Grove.

Residents have access to healthcare through nearby hospitals in the Honolulu area. Adventist Health Castle, which is located in Kailua, is one of the main options. In addition, Kalapawai Market is a local favorite to grab coffee, ube scones, and other treats.

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Kailua is home to many beaches for swimming and watersports, including Kailua Beach Park. Lanikai Beach is a public beach within a residential neighborhood, with no lifeguards, restrooms, or public parking lot. For walking and biking, Kawainui Marsh Wildlife Sanctuary is a popular dog-friendly wildlife sanctuary with a scenic trail.

Haleʻiwa

Aerial view of Haleiwa, Hawaii.
Aerial view of Haleiwa, Hawaii.

Hale’iwa is known for its slower pace and strong connection to Oahu’s North Shore coastline. This historic North Shore town is said to be the quirkiest and has a population of under 5,000. It maintains a small commercial core while serving nearby rural communities.

Healthcare is available through clinics in Waialua and through The Queen’s Medical Center – Wahiawā in central Oahu.

Notable landmarks in Haleʻiwa include Haleʻiwa Beach Park, a popular spot for fishing and sunset views, and Waimea Bay, known for its large winter surf and summer swimming conditions. The nearby Banzai Pipeline draws surfers from around the world during big-wave season on Oahu’s North Shore. Residents also spend time at Haleʻiwa Aliʻi Beach Park, which has picnic areas and shoreline walking paths.

Wahiawa

Waikele Premium Outlets in Honolulu County, near Wahiawa, Hawaii.
Waikele Premium Outlets in Honolulu County, near Wahiawa, Hawaii. Image credit ARTYOORAN via Shutterstock.com

Wahiawa is a central Oahu community with a population of roughly 17,000. It sits between the island’s north and south regions, and provides a quieter inland setting while still allowing access to both Oahu’s north and south coasts.

Healthcare in Wahiawa is available through in-town facilities, such as The Queen’s Medical Center – Wahiawā.

Local landmarks include Lake Wilson, where residents fish and kayak, and the Wahiawa Botanical Garden, known for its large tropical trees and walking paths. Nearby Schofield Barracks remains one of the largest military installations in Hawaii and shapes much of the area’s economy. Residents also rely on Whitmore Village for local businesses, neighborhood services, and access to agricultural areas outside town.

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Makawao

The town of Makawao sits on the slope of the Haleakala volcano in Maui.
The town of Makawao sits on the slope of the Haleakala volcano in Maui.

Makawao is a small town in upcountry Maui with fewer than 10,000 residents. Its higher elevation gives the area cooler temperatures than much of coastal Maui, especially during the evenings.

Makawao maintains a rural atmosphere while still keeping residents close to shopping and healthcare in nearby Kahului and central Maui for routine and specialized care.

Residents enjoy art galleries, and nearby access routes to Haleakalā National Park, which draw both residents and visitors into Maui’s upland landscapes. The community also gathers around Oskie Rice Event Center, which hosts rodeos and local events throughout the year, while Pukalani Country Club provides golf and recreation with views of central Maui.

Pāhoa

Downtown street in Pahoa, Hawaii.
Downtown Pahoa, Hawaii. Image credit Chris Allan via Shutterstock

Pāhoa is a small town on Hawaii Island with fewer than 1,000 residents. The community has a slower pace of life and a strong local character shaped by East Hawaii’s volcanic landscape. Residents access healthcare through clinics in nearby Hilo and facilities connected to Hawaiʻi Health Systems Corporation in East Hawaii.

Local landmarks include Lava Tree State Monument, where lava formations surround walking paths through tropical forest, and the historic downtown which still contains several older storefronts and small local businesses such as Tin Shack Bakery. Nearby Pohoiki Black Sand Beach has become a popular coastal gathering area following recent volcanic activity, while the former Ahalanui Park site (destroyed by the Kīlauea lava flow in 2018) remains an important part of the region’s history and shoreline identity.

Honoka’a

Overlooking Honoka'a, Hawaii.
Overlooking Honoka’a, Hawaii.

Honokaʻa is a small plantation-era town on the Big Island of Hawaii. With fewer than 3,000 residents, its historic main street reflects its sugar industry past with preserved storefronts and a compact town center that still serves the surrounding Hamakua Coast communities.

Residents access healthcare through Queen’s North Hawai’i Community Hospital in nearby Waimea, which provides essential services for the region.

Along the main corridor, residents frequent shops such as Tex Drive-In, known for its malasadas, and Cafe Il Mondo, a long-running local café. The nearby Kalōpā State Recreation Area offers forest trails and native vegetation, while the Hamakua Coast provides scenic coastal drives with waterfalls and ocean views. Routes toward Akaka Falls connect the town to one of the island’s most visited natural landmarks.

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Hawaii Retirement Across the Islands

Retirement spots in Hawaii are found across the islands, each with its own pace of life. Towns like Kailua-Kona and Līhuʻe keep residents close to healthcare, services, and coastal scenery, while places such as Waimea, Makawao, and Honokaʻa offer quieter inland settings with strong local character. Others, including Hilo, Kapaʻa, and Haleʻiwa, balance everyday conveniences with beaches, parks, markets, and community gathering places. As people in Hawaii look for more space, fewer crowds, and reliable access to care, these towns show how varied retirement living can be across the state.



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I took my 30-year-old son on a vacation to Hawaii. We had to set ground rules first.

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I took my 30-year-old son on a vacation to Hawaii. We had to set ground rules first.


I live in New York City. My 30-year-old son, Alec, lives across the country in Southern California. When I visit, I respect that he has his own busy, adult life. While I’d like nothing more than to spend every minute with him, I’m proud of his independence and try not to monopolize his time.

Alec has a roommate and no space for an overnight guest. When I’m on his home turf, I stay in a hotel or with a friend.

When he comes to NYC for the holidays, his schedule is packed. Plus, with the entire family under one roof, it can be tough to carve out one-on-one time.

I don’t feel shut out of Alec’s life, but I do miss spending quality time with him, so I floated the idea of a mother-son vacation.

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He set a few ground rules before we started planning

Alec was vocal that for our getaway to work, we’d need to approach it as equals. This may sound deceptively simple, but it took lots of self-control on my part.

Little kids and I pair like milk and cookies. I did my graduate studies in early childhood education and taught preschool for years. Parenting young kids is never easy, but it felt instinctive. It grew harder as my children grew older.

Alec is my firstborn, and my parental grip was tightest around him. When he was a teenager, he told me I didn’t understand that teens needed autonomy. At the time, he was correct, but over the years, I’ve worked hard to pacify my bossy instincts.

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This time, I would welcome his voice in planning our vacation.

Alec brought up another rule: that part of being equal should include sharing expenses. I gifted Alec his airline ticket using miles, and we split additional expenses.

Choosing a destination

Alec had four days off work over Memorial Day Weekend. I advocated for a location that wasn’t too hot, as I had suffered a bout of heatstroke in Greece last summer. A yoga class nearby would be a bonus.

Alec made a case for Hawaii. He’d never been, but its laidback reputation appealed to him. He said he wanted to destress at a resort and eat poke every day.

Hawaii is special to me. I first visited when I was a kid, spending a summer at my aunt and uncle’s home in Waianae on Oahu. The idea of sharing Hawaii with Alec was exciting.

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From a practical point of view, Hawaii made sense. There are numerous nonstop flights from LAX, Alec’s home airport. I was going to be in Denver for work, so I was already heading in a westerly direction.


Allison Tibaldi  and her son in front of the ocean in Hawaii wearing leis

The author loved spending time with her adult son. 

Courtesy of Allison Tibaldi



Each of the Hawaiian Islands has its own flavor. We had lots of options and weren’t quite sure how to narrow them down.

Alec is a fan of the television cooking show “Top Chef.” During his online research, he learned that former contestant Sheldon Simeon was scheduled to be the visiting chef at the Ritz-Carlton O’ahu, Turtle Bay on the island’s North Shore on the Saturday night of our trip.

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The Hawaiian-born chef would be preparing a multi-course dinner using island-grown ingredients. I’m all about exploring local culture through food, so it seemed like a jackpot for both of us.

After we booked the dinner, we figured it made sense to stay at the Ritz-Carlton.

Balancing time together and separately was key

Another boundary we set for our vacation was balancing time together with time apart.

Each morning, Alec surfed, and I swam laps in the pool. I signed up for a lei-making workshop while he attended a tennis clinic.

In a perfect world, we would have reserved individual rooms; however, we shared a room for economic reasons.

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We were still able to maintain boundaries and give each other privacy as our room had a comfortable ocean-view patio, perfect for reading and relaxing.

Meaningful conversations are what stand out

Time together sparked the meaningful conversations and connection I had longed for.

On May 24, I mentioned that it was my beloved dad’s heavenly birthday. Alec shared tender memories of his grandpa and told me that my dad had been a father figure for him, too, teaching him lessons that continue to impact his life. It made me teary.

We also had an intelligent discussion on income inequality. Alec overheard a group of vacationing doctors and a group of vacationing teachers chatting in the Jacuzzi. He said the doctors worked very long hours without complaint, while the teachers complained nonstop about their overwhelming workload. This led to a conversation between Alec and me about teachers being underpaid and undervalued.

As a former teacher, I found that my son’s thinking about socio-economic issues that hit so close to home really resonated with me.

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Our mother-son vacation brought us closer

Our mother-son vacation was a success. Alec ate plenty of poke. I got to practice yoga. Together, we swam in the Pacific, walked trails surrounded by gardenias, and enjoyed a delectable Hawaiian dinner.

As much as I loved our activities, it’s the memories of our personal and poignant conversations that are etched in my heart.

I can’t wait to travel with Alec again.





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Waianae encampment deadline extended amid pushback from lawmaker, community

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Waianae encampment deadline extended amid pushback from lawmaker, community


HONOLULU (HawaiiNewsNow) – A state senator is challenging the Department of Land and Natural Resources’ (DLNR) decision to extend the deadline for the Puuhonua O Waianae (POW) encampment at Waianae Boat Harbor.

It comes as state and community leaders continue efforts to relocate residents to a permanent site.

The deadline was originally set for the end of June and has been pushed to Oct. 16.

State Sen. Samantha DeCorte said the extension marks the third delay in the relocation process since the original notice to vacate was issued last year. The initial deadline was Nov. 27, 2025, followed by extensions to April 30 and June 25 before the most recent extension.

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DeCorte criticized the repeated delays during a press conference on Saturday.

“We are calling on DLNR Acting Chair Ryan Kanakaole, members of Puuhonua O Waianae, and the governor’s office to do what they said they would do. Complete the transition, honor the commitment, and bring this process to a close. After 20 years, another extension is not the solution,” DeCorte said.

She added concerns remain around public safety near the harbor, including reports of vandalism involving fishing equipment and conditions she says affect families and students traveling through the area.

“Fishermen have dealt with vandalism (and) theft of their equipment. Public safety concerns have persisted, and kids have to walk past unsafe conditions just to get to school.”

DLNR said the extension is intended to provide additional time for the relocation of the POW community to a nearly 20-acre site in Waianae Valley, while construction continues at the mauka housing development.

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Kanakaole said in an email sent to DeCorte Friday that POW requested a deadline extension to vacate by the end of November, and the department, along with the governor’s office, reached an agreement on the October move-out deadline.

“DLNR, POW, and the Governor’s Office worked through what remains to be completed and established a reasonable timeline tied to actual relocation, cleanup, and closure activities and to provide for the most orderly and voluntary transition, which will ultimately lead to a solution that will last,” Kanakaole’s email said in part.

He added that more than 100 people remain at the site and POW leaders said that number should substantially reduce over the next several weeks, “potentially by nearly half within the next month.”

Read Kanakaole’s full email to DeCorte here.

The agency said it is coordinating with community leaders to ensure residents can relocate safely and to support cleanup and transition efforts at the harbor.

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The relocation site has been part of a long-term plan tied to the late community leader Twinkle Borge, who envisioned moving families from the harbor into permanent housing.

Community leaders with Puuhonua O Waianae said the process remains complex and cannot be completed immediately.

Kala Paishon, a community leader with the encampment, said some residents are still unable to move because housing units at the new site are not yet complete. He also said limited transportation and volunteer support make moving difficult for some families.

“We do have some people that volunteer their time to help our people move. We’re limited on our vehicles, but we do what we got to do to move the people up there,” Paishon said.

He added that many residents have deep ties to the harbor after years of living there.

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“Some people have been here 10-plus years,” Paishon said. “This is the memory they have, and this is where they felt like home.”

Paishon also said crews are working to gradually transition residents while maintaining cleanup efforts at the site.

“We’re making sure everybody moves up there safely… at the same time, we’re still cleaning up our opala down here.”

DLNR said it continues to work with community leaders and the governor’s office to move the relocation process forward in the coming months.

Copyright 2026 Hawaii News Now. All rights reserved.

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Office of Hawaiian Affairs Responds to Senate Bill Involving Pōhakuloa – Big Island Video News

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Office of Hawaiian Affairs Responds to Senate Bill Involving Pōhakuloa – Big Island Video News


(BIVN) – The Office of Hawaiian Affairs (OHA) says it is in alignment with provisions in the Fiscal Year 2027 National Defense Authorization Act dealing with military-leased lands in Hawaiʻi, including the Pōhakuloa Training Area. 

In a news release, OHA said it is encouraged by the bill’s “clear movement away from condemnation and toward negotiated solutions” for the approximately 19,700 acres of state lands at Pōhakuloa, and 450 acres at Kahuku. “The process outlined is consistent with OHA’s long-standing position opposing condemnation – whether forcible or ‘friendly’ – and insisting that lands held in public trust remain in the public trust and continue benefiting Native Hawaiians and future generations of Hawaiʻi’s people.” 

The U.S. Senate Armed Services Committee recently passed the Fiscal Year 2027 National Defense Authorization Act, or NDAA. The bill is expected to advance to the full United States Senate for consideration by the end of July 2026, OHA says. 

In a June 12th news release, U.S. Senator Mazie Hirono (D, Hawaiʻi) said she voted against the NDAA. Hirono is a senior member of the Senate Armed Services Committee (SASC) and Ranking Member of the Readiness and Management Support Subcommittee. 

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“I’m proud to have secured numerous provisions in the Senate’s FY27 NDAA that invest in military readiness, Hawaii, the Indo-Pacific Region, and our servicemembers and their families, while also holding the Army accountable on the military training land lease negotiations,” Hirono stated at the time. “However, I could not in good conscience vote to advance a bill that paves the way for an up to 40% increase in year-over-year Department of Defense spending, especially as this administration wages an illegal war in Iran with no plan or end in sight.” 

Hirono said the bill “directs the Secretary of the Army to seek from the State of Hawaii, on terms acceptable to both the Army and the State, a renewal of expiring training land leases. As part of this, requires the Army to expeditiously resubmit their Environmental Impact Statements (EISs) for the leased lands and address deficiencies identified by the Hawaii Board of Land and Natural Resources.” 

Soldiers assigned to the 209th Aviation Support Battalion, 25th Combat Aviation Bridge qualify on the M2 Machine Gun during a training rotation at Pohakuloa Training Area, Hawaii on March 1, 2026. Soldiers conducted live-fire training, improving their proficiency with crew-served weapon systems and enhanced force protection capabilities in an expeditionary advanced base operations environment. (U.S. Army Photo by Sgt. Olivia Cowart)


OHA noted Section 2864 of the NDAA also requires a report to Congress on the steps and proposals taken to advance lease renewals, within 60 days from the NDAA’s enactment.

“The Senate Armed Services Committee’s action reflects meaningful progress in acknowledging Hawaiʻi’s unique legal and cultural context,” stated OHA chair Kaialiʻi Kahele. “The removal of condemnation as an option and the requirement for renewed environmental review are consistent with what OHA has long advocated – that these lands must not be permanently alienated and that Hawaiʻi’s concerns must be fully addressed in good faith. Congress appears willing to respect Hawaiʻi’s laws and institutions. The opportunity before us now is to fully embrace the responsibilities and authorities those laws entrust to us. OHA will continue to ensure Native Hawaiian rights and public trust responsibilities remain central to any future decisions.”

OHA has been holding high-level meetings in Washington, D.C. concerning the military lease renewals.

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An AH-64 Apache Helicopter flight crew assigned to 2nd Squadron, 6th Cavalry Regiment “Sabers”, 25th Combat Aviation Brigade, execute an aerial gunnery designed to certify pilots on their weapons systems at Pohakuloa Training Area, Hawaii from February 2-25, 2026. (U.S. Army Photo by Sgt. Olivia Cowart)

OHA says it is also actively moving forward with a comprehensive Ka Paʻakai Analysis for Pōhakuloa Training Area. “The Board of Trustees has already approved a Permitted Interaction Group allocation of $60,000 to support this work, and OHA is finalizing a memorandum of understanding with DLNR to complete the work,” the Office stated. The analysis “will help create a more complete record of the cultural, historical, and community connections to these lands, providing decision makers with information necessary to evaluate potential impacts, identify appropriate protections, and fulfill their responsibilities under Hawaiʻi law.”

From the OHA news release:

OHA also notes that the NDAA contemplates the pursuit of future lease arrangements pursuant to Section 2667 of Title 10, United States Code. As discussions continue regarding potential lease terms, community benefit commitments, land-back and lease-back models, and other components of any future agreement, OHA believes those arrangements must remain consistent with Hawaiʻi’s environmental laws and public trust obligations. Any benefits derived from renewed use of these lands should reinforce the purposes of the public trust, protect traditional and customary Native Hawaiian practices, honor the history and significance of these lands, and preserve the value they were intended to provide for Native Hawaiian beneficiaries and future generations of Hawaiʻi’s people.



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