Maui for Retirees

Newest Maui Article: Lahaina Gateway

From basking in the sun on a glorious beach to seeing a sunrise from a volcanic peak, Maui is hardly an age-specific place.

Whether you’re an octogenarian intent on finishing a waterfall hike, or you just blew out the candles on your retirement cake, here are Maui’s best activities for those in their golden years:


Attend a Luxurious, Oceanfront Luau

Maui oceanfront luau

Second to aloha, “luau” may be the most well-known Hawaiian word. And for good reason: While luaus are traditionally known as aha’ainas, the contemporary take on the ancient custom is one of the finest forms of entertainment in Hawaii. Maui boasts a number of fantastic affairs, but one of its newest—The Feast at Mokapu—is distinguished from the rest.

Presented on the shoreline lawn at the Andaz Maui at Wailea Resort, the sterling presentation combines the fare of acclaimed chef Isaac Bancaco with Hawaii’s enthralling history. The intimate event—it seats 150—is complete with cultural demonstrations, live music, Polynesian dancing—and one of the South Side’s celebrated sunsets.

Gorgeous and authentic, it’s a lovely way to get a taste of bygone Hawaii.  If you’re on the west side, look through some of the best Maui luaus to find one near you.

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Escape to Hana

escape to Hana

In recent decades, Maui has assumed a buzzy, cosmopolitan feel—but that doesn’t mean its natural gems and historical import have vanished. Driving the Road to Hana—a serpentine route comprised of stone bridges, stunning vistas, and 600-plus turns—is just one example of this. The three-hour journey can be taken on your own, of course, but handing over the reins to an expert is the choice way to go.

Road to Hana Tours provides locals and guests with the supreme Hana experience, transporting visitors from their accommodations to the East Side’s most radical places. This locally owned and operated tour business takes you in comfort cruisers, which are a huge part of their draw—not only do they seat no more than 12 guests, but they also feature extra-large viewing windows.

It’s the perfect way to absorb the surroundings—and get lost in the lush rain forests around you.

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Sail the Sunset

sailing sunset in Maui

The Kai Kanani has gone down in Maui history for delivering one of the most sumptuous sunset sails on the island. Having served the Valley Isle for three decades, they’ve got their strategy down pat. Their winning vessel—a deluxe catamaran—launches from one of Makena’s most exquisite beaches before Maui-raised artist Brother Dwight serenades the crowd with his music.

Meanwhile, first-rate eats, prepared by Wailea’s The Market, are served up in style as the sun skips beyond the horizon. One could say the champagne toast culminates the night, but we’d argue that it’s the island’s dusk-time splendor that takes top prize.

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Journey to Maui’s Remote “Forbidden” Coast

Molokini trips

Charters abound on Maui, which is no wonder: The waters that surround the 727 square mile island redefine luminous. Redline Rafting Co. takes you into the heart of the Pacific’s action with their Molokini snorkeling tours.

Beginning in beachy Kihei, the excursion stops at the volcanic caldera off of Maui’s southwestern shore, where ocean lovers can don a snorkel mask to see awesome aquatic critters. From there, the affable folks who run Redline Rafting take guests to the site of Maui’s last lava flow—a picturesque slice of the island that features caves, blowholes, and spinner dolphins. Given the small size of their vessels, you’re destined to have an intimate and mesmerizing experience.

(Not into swimming or snorkeling? Not to fret: The vistas alone are well worth the trip to Molokini Crater.)


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Private Sunset Sail

Maui For Retirees Private Sailing Adventure

If you fancy a more exclusive experience, consider a private sunset sail with Maui Custom Charters. Choose from the sporty S/V Artemis, a 47′ Leopard sailing catamaran, or the S/V Nova, a 42′ Catalina MKII sailing yacht. Each welcomes aboard up to six guests for a wholly intimate and unforgettable sunset sail around Ma’alaea Bay (whale watching, snorkeling, and customizable tours are also available). While a private cruise on Maui is memorable in itself, the hospitable crew at Maui Custom Charters takes the experience to the next level— on hand to whip up tasty appetizers, give sailing lessons to keen learners, or simply offer five-star service. Not to mention, the views from the water are second to none. 

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Tour a Botanical Garden—and Dine with a View

Maui Tropical Plantation

Maui Tropical Plantation has been delighting visitors since its inception over thirty years ago. Situated at the base of the West Maui Mountains, the working farm and tourist destination teems with activities: a coffee roaster and café, zip-lining tours (in case you haven’t had enough), shopping, historical pieces, an ice cream kiosk, and more. One of its biggest allures is the opportunity to take a tour of its plantation, where organic crops give way to bright, wonderful flowers. (You can also take home some of their jewels at Kumu Farm’s outdoor stand.)

After feeding the ducks in the plantation’s lagoon, step into The Mill House (recently under Cafe O’Lei operations). Deriving their menu from the freshest produce on the island—including those that grow on and around the plantation— if you love Cafe O’Lei, you’ll love The Mill House’s meals. Intrigued by Hawaii’s agricultural past? Take a minute to admire the relics that embellish this unique Maui restaurant.

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Witness the Sunrise of a Lifetime

haleakala sunrise

Haleakala is, in short, a sight to behold: Ascending 10,023 feet into the sky, it cradles one of the largest dormant volcanic craters in the world. Given its height, it ought to arrive as no surprise that its sunrises reaffirm the real definition of awesome. So striking are Haleakala’s dawns, in fact, that they require registration with the National Park Service, oftentimes booking up months in advance. You can navigate the corkscrew Haleakala Highway on your own—or you can let Haleakala EcoTours take the helm.

This eco-friendly company provides NAI-certified guides, who offer a telling and fascinating look at Haleakala’s history before giving you a chance to explore the park (and to revere its unique species). Post-sunrise, Haleakala EcoTours will take you through Upcountry, the North Shore, and Central Maui, thereby allowing you to appreciate, first hand, what Haleakala helped create: An island marked by exceptional beauty and grace.

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Relocating to Maui

Maui for retirees

Perhaps you’ve always dreamed about living on Maui, but real-world obligations – your job, kids – have always kept you tied down. But now, here you are, retired and ready to pull the trigger. Whether you choose to settle in a beachside condominium or in a plantation house in Upcountry’s cool pastureland, Maui’s idyllic beauty and the active lifestyle that goes along with it are sure to keep you happy and healthy.

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Indeed, its leading activities—snorkeling, swimming, and hiking, to name just a few—are ideal for anybody from one to one hundred.

And yet, Hawaii’s second-largest island has special appeal for seniors, rendering it Kiplinger’s second-highest-ranking place to retire in the U.S.—and a splendid spot to visit.

Maui for retirees