7 of the Friendliest Towns To Retire In Hawaii
The beautiful state of Hawaii has long been a dream retirement destination for many, and it’s easy to see why. When most people think "Hawaii", the first things that often come to mind are sandy beaches, drinks with umbrellas in them, surfing, beautiful weather, and a famously laid-back attitude. The Aloha State comprises 137 islands covering approximately 10,931 square miles, featuring diverse scenery that includes forests, waterfalls, rivers, and mountain ranges. All told, there are plenty of options to choose from if one is looking to spend their golden years living in paradise in the Pacific, so here are seven of the friendliest towns to retire in Hawaii.
Wailuku - (Maui)
Perhaps one of the easiest ways to describe the town of Wailuku, on the island of Maui, is to simply call it breathtaking. Home to about 17,697 people, this town, just west of the ʻĪao Valley, offers amazing views of the West Maui Mountains, which look like something straight off a postcard. Residents and visitors alike enjoy spending time at Kepaniwai State Park. Spread across more than seven acres, the park is a great place to enjoy the local scenery while grilling something up at one of the provided BBQ spots.
To learn about the area’s local history, visitors can stop by the Maui Historical Society Museum. One of the best parts about Wailuku is its thriving arts community. Stop by the historic ʻĪao Theater, which has showcased plays, musicals, and more since it opened in 1927. The area’s almost-always-beautiful weather makes the town a great place to take a stroll through areas like the Wailuku Civic Center Historic District, which features numerous historic buildings, including the courthouse built in 1907.
Kaunakakai - (Molokaʻi)
On the island of Molokaʻi sits the town of Kaunakakai. This town is what many people imagine when they dream of life in Hawaii. The area’s climate is classified as tropical savanna, meaning it enjoys an average year-round temperature of about 75°F (24°C). Once the summer home of King Kamehameha V (Lota Kapuāiwa Kalanimakua Aliʻiōlani Kalanikupuapaʻīkalaninui), the town is currently home to around 3,419 people.
Getting there is easy thanks to the town being only about six miles from Molokaʻi Airport. While in town, residents can relax and take in the views at Kapuāiwa Coconut Grove, listening to the breeze move through the trees. The grove is private property, but the view is no less spectacular. Speaking of coconuts, for anyone who has ever had the urge to decorate and mail a coconut to a friend or loved one, be sure to stop by Post-A-Nut, a service that does exactly that.
One of the town’s most distinctive landmarks is the longest pier in the state, found at Kaunakakai Harbor — perfect for an evening stroll while enjoying a cold drink. For a great meal while in town, stop by Paddlers Restaurant & Bar.
Lānaʻi City - (Lānaʻi)
Located on the island of Lānaʻi, this town of 3,332 people was once the epicenter of the Dole Pineapple Company. It remains the only intact former plantation town on any of the Hawaiian islands, a complicated and often troubling history that makes for a fascinating present. Today, the area surrounding the company’s former headquarters is filled with shops like The Local Gentry, a funky boutique that’s a perfect place to pick up gifts.
To learn about the area’s rich history, visit the Lānaʻi Culture & Heritage Center, which is always looking for volunteers, a great way to spend one’s golden years. Cat lovers can spend time at the Lānaʻi Cat Sanctuary, where more than 700 cats live on a beautiful 4 acre property. Visitors can learn how the cats are cared for and make donations while there. Should any medical needs arise, the Lānaʻi Community Hospital is fully staffed and ready to serve residents.
Kailua-Kona - (Big Island)
Located on Hawaii’s Big Island, the town of Kailua-Kona, often simply called Kona, is home to just under 20,000 people. It’s the kind of seaside town most people picture when they imagine Hawaii. Sitting along the Pacific coast, Kona’s beaches have long been a haven for surfers from around the world.
Of course, one doesn’t need to be a surfer, or even a fan of surfing, to enjoy the alabaster sands and crystal-clear water at Laʻaloa Beach Park (Magic Sands). The beach is perfect for swimming, jogging along the shoreline, or simply enjoying the sunshine and ocean breeze while reading and browsing one’s favorite travel website.
For a uniquely Hawaiian experience, the Royal Kona Resort hosts a Voyagers of the Pacific luau, complete with a traditional pig roast, cultural dancing, and refreshing drinks. After a hearty meal, a walk to Huliheʻe Palace is well worth it. Built in 1838, the palace was once home to High Chief John Adams Kuakini and today stands as a monument to one of Hawaii’s most important historical figures.
Hāna - (Maui)
The charming town of Hāna on the island of Maui is perfect for those who truly want to get away from it all. Home to just over 1,500 people, Hāna is one of the most isolated towns in the state. Despite its remote feel, Hāna is accessible by land, sea, and air thanks to the Hāna Highway, Hāna Airport, and its coastal location.
Residents and visitors can learn about the town’s history at the Hāna Cultural Center & Museum. Visits are by appointment only, so be sure to call ahead. One of Hāna’s must-see attractions is Red Sand Beach (Kaihalulu Beach). Small and secluded, it’s best visited early in the day, but its striking red sand and clear blue water make the effort worthwhile.
As beautiful as the beaches are, Kahanu Garden and Preserve is Hāna’s crown jewel. The preserve is home to Piʻilanihale Heiau, one of the largest heiau in Hawaii, and offers stunning views of lush forests, ocean waters, and distant mountains. Just be sure to bring a fully charged camera.
Makawao - (Maui)
Located in Maui’s rural, farming-focused interior, Makawao is a charming community of 7,297 people. In many ways, it feels like a laid-back mainland farming town just with much better weather. Residents can decorate their homes with locally made art from places like Sherri Reeve Gallery & Gifts.
For those curious about Hawaii’s agricultural roots, the Maui Pineapple Tour offers a look at how one of the island’s most famous fruits is grown. And here’s a bit of fun trivia for pizza lovers: Hawaiian pizza was not invented in Hawaii. It actually originated in a bowling alley in Ontario, Canada, with the name chosen purely for marketing purposes.
Thanks to Hawaii’s climate, nearly every day is a good day for golf. Pukalani Country Club, just outside Makawao, features 18 holes of lush greens with views of the Pacific. Just remember to shout “fore!”
Captain Cook - (Big Island)
Home to about 3,253 people, the town of Captain Cook was named after the famed explorer Captain James Cook, who spent his final days in the area before his death in 1779. Today, the community is a welcoming and relaxed place well suited for retirement.
Coffee lovers will enjoy visiting Hala Tree Coffee Farm, which offers tours of its fields and sells freshly roasted coffee on site. The tours provide insight into one of the world’s most beloved beverages while offering a chance to enjoy the area’s fresh air and scenery. For local history, the Kona Historical Society is well worth a visit.
Captain Cook’s calm atmosphere makes it easy to slow down and enjoy life. For a great meal, stop by Shaka Tacoz, a popular food truck known for its fish tacos. The town is also just 12 miles from Kailua-Kona, providing convenient access to larger services if needed.
It’s easy to think of Hawaii as just a place of surf, sand, and sunshine, but the Aloha State is so much more than that. Its deep history, unique culture, and distance from the U.S. mainland truly make Hawaii a world of its own. Anyone who visits the islands wishes they had more time to stay and retirement offers exactly that.
With warm weather year-round, residents can enjoy activities like gardening, golfing, and swimming no matter the season. No matter what a person’s ideal version of retirement looks like, Hawaii offers something for everyone. From rugged landscapes to awe-inspiring beaches, it has it all the only thing missing is you.
