Your Trip of a Lifetime

9 Days on Maui

9-day Maui itinerary

A vacation ought to be synonymous with stress-free, especially if you’re holidaying in Hawaii—a place that brings new depth to the whole concept of “no worries.”

And while planning 9 days on Maui may be exhilarating for some, wouldn’t you rather arrive on the island caring about little more than what to wear out for a Mai Tai?

With that in mind, we’ve done the legwork for you, pulling together the ultimate 9-day Maui itinerary—one that mixes sun and sand, culture and entertainment, glamour and Mother Nature, fun atend relaxation.

So? Let’s get started.


Day 1:


Rise with the mynahs and hit up one of Maui’s java cafés (if you’re staying in Ka’anapali, be sure to check out Island Vintage Coffee for a cup of farm-fresh, 100% Kona coffee) before gearing up for your first adventure: A sun-splashed snorkeling trip with a Molokini Snorkeling Tour.

Ohana-owned and eco-friendly, Redline Rafting will provide you with an ultra-personalized, private tour of Maui’s gorgeous, unspoiled waters and Lanai’s pristine, beautiful reefs. Dive into the Pacific, savor sights of tropical fish and Hawaiian Green Sea Turtles, and witness the splendor of Hawaiian Spinner Dolphins, all while the staff provides fascinating commentary.

Molokini Crater

Happen to be vacationing on Maui between November and May? You’re in luck: Humpback whales migrate to Hawaii during these months to breed, calve, and frolic—thereby giving you an unforgettable experience.


Take advantage of the fact that you’ll be de-boarding in Lahaina Harbor—the port’s surrounding environs teem with outstanding eateries. Grab a seat at Kimo’s Lanai Bar, where you can soak up more of Maui’s beauty while sipping a Maui Mojito and snacking on a plate of macadamia nut-crusted calamari.

Lahaina Harbor

Re-energized, peruse Front Street’s boutiques for a sarong or a pair of surf shorts—trust us that they’ll come in handy. Then, slip over to the Lahaina Jodo Mission in Mala Wharf. Featuring one of the largest replicas of Buddha outside of Asia, this peaceful, lovely spot tells the story of Hawaii’s Japanese history.


There’s no better way to leap into your Hawaiian escape than with a wonderful luau.

For the ultimate in authenticity, look no further than the Grand Wailea Luau. Located mere feet away from the moonlit water, this traditional Polynesian celebration is all about honoring Hawaiian and Maui history, from the lauhala mats upon which you’ll eat your feast and the customary imu ceremony to the sweet potato beer, Uala Lager, served by Maui Brewing Company.

Maui Brewing Company

Frequently deemed the most riveting luau on the Valley Isle, this memorable performance includes some of the finest Hawaiian and Tahitian dancers in the islands. As cultural critic and homegrown-Hawaiian journalists have said, “this is the best commercial luau I’ve ever been to.”

Grand Luau


Day 2:


Rise before the mynahs this time—as in, set that alarm for super-early (bear with us—it’ll be well worth it). Your second day on Maui will be spent on lofty grounds—as in, the 10,023-foot peak of the world’s largest dormant volcano.

Aptly called “House of the Sun,” Haleakala is revered for its height, history, and grandeur—so much so rising early to catch sunrise from its summit is one of the most popular activities on the island.

Translation? Morning excursions offer brilliant colors shearing the seemingly limitless sky as the ocean—and island—shimmer below.

Post-awe, lace up your sneaks for one of the most awesome rides of your life: Haleakala Bike Tours offer 16 miles of downhill biking with views that will blow your mind. They're one of only 4 companies taking visitors to the summit, thanks to their partnership with Haleakala National Park.


Situated among rolling green hills and misty forests, O’o Farm—an eight-and-a-half-acre organic orchard renowned for its bounty—presents panoramic vistas of Maui’s breathtaking coastlines and cool, even blissful weather.

OO Farm

Which will work well in your favor as you go on an informational, interactive tour of the farm to harvest your own lunch. Prepared by celebrated chef Daniel Eskelsen, this meal (past creations include fresh fish sautéed with lemongrass oil and served with O’o Farm vegetables) is one of the most delicious educations around.


Go out of your way to catch a stellar sunset and live tunes by heading to the southern stretch of the island. While all of the beaches in South Kihei, Wailea, and Makena are splendid—think: white sand beaches, aqua waters, swaying palms—Keawakapu seems to have been perfectly positioned to bestow the best in sunset views.


Nestle down on the beach’s bank of grass and swoon as the sun disappears between Lanai and West Maui’s edge. And when darkness hits? Meander up the way to Monkeypod. Helmed by Peter Merriman—one of Hawaii’s most preeminent and innovative chefs—this bright, buzzy place features a superb pau hana and live music by local talent.


Day 3:


After a morning walk to see the sunrise surfers at Cove Park (and sip on a cappuccino from Belle Surf Café), make your way to the central isthmus of the island, where you’ll be soaring into the sky on a one-of-a-kind voyage.

Maui Helicopter tours

Aboard a Maui helicopter tour, that is. Tours of Maui’s hidden gems, from Hana’s remarkable waterfalls to West Maui’s towering (and humbling) bluffs, are awaiting you! The Molokai tour is especially electrifying—it swoops passengers above the largest sea cliffs in the world—and each journey is accompanied by insightful facts about Hawaii’s history, geology, and culture.


It’s safe to assume that one of the primary reasons you chose Maui as your destination is the extraordinary sand and surf.

Relish both at Ho’okipa Beach Park. Located on Maui’s rugged North Shore, this is inarguably one of the best breaks on the island—and the number of kite boarders, surfers, and windsurfers serves as testament. While the swells may be too rough and large for newbies (it’s also a patently local spot), you can have just as much vicarious fun by spreading out a towel and taking in the marvels.

Hookipa Turtle

Of those? Parades of honu (Hawaiian Green Sea Turtles), who are just as passionate about the glassy water as the visitors and kama’aina. These intriguing creatures tend to make a grand appearance around sunset, when they come ashore to bathe in what’s left of the warmth.


Mama’s Fish House is a must-do on every Maui itinerary. And for good reason: Local fishermen take early morning trawls to deliver the freshest, most marvelous-tasting fish in Hawaii. (Top honors go to their crab-stuffed, Ke’anae-caught mahi mahi and their Papio sautéed with Hamakua mushrooms, lemon-butter, and garlic.) Refined and romantic—and equipped with heart-melting views of the Pacific—this is the place to dine when visiting the Valley Isle. Post-dessert—try their guava cheesecake with Hana breadfruit—head into Paia, where you can ogle local craftsmanship at Maui Crafts Guild and Indigo.

Mama's Fish House


Day 4:


Make your morning memorable with brunch at Paia Inn—a hip, bohemian lodge whose café and juice bar offers excellent eats in an elegant-but-casual venue. (Their Avocado Toast with tomato crudo, sea salt, and radish is particularly divine.) Relish the Paia Town people watching and scenery—including, perhaps, a celebrity sighting—before hopping into your car: You’re about to head out on the ride of your life.

paia in the morning


The Road to Hana has been called many things, from “the most beautiful road in the world” (Sunset magazine) to “one of the world’s best drives” (Travel + Leisure), but we’ll sum it up in one word: Wondrous.

fun in Hana

Your journey begins where you stopped for breakfast. Following a quick stop at Mana Foods for drinks and wholesome snacks, hop on the heavenly highway—upon which you’ll ooh and aah for the next fifty-some miles.

Your first stop on this iconic route ought to be Honomanu Bay County Beach Park, a discreet cove framed by lush, formidable headlands. Walk the nickel-hued sand and snap a few pics—the verdant surroundings are so green they’re startling.

Honomanu Maui

Next up? Ke’anae Peninsula—a historic fishing village (and home to that mahi mahi at Mama’s) that’s retained its Old Hawaii sensibility. While there are no swimmable beaches in this enclave, its enchanting history (it once housed the prisoners responsible for constructing parts of the Road to Hana, if ever there’s a feat), tropical flora, and serene chapel will mentally prepare you for two days of otherworldly serenity.

Black Sand

Which you’ll find more of in spades at Waianapanapa Beach Park, a striking stretch of exoticism that’s unlike anywhere else on the planet. Here you’ll find a beach comprised of onyx sand, blowholes that elicit one wow after another, underwater grottos, lava tubes, a seabird colony, even pools that run red certain times of the year, thanks to schools of tiny shrimp. Prepare to have a blast—this 120-acre state park supplies hours of amazement.


One of the points of sojourning to Hana is to receive the kind of sleep you likely haven’t enjoyed in years—a possibility that’s made manifest at the peerless Hana-maui Resort, Maui, an experiential resort that provides the utmost in comfort and calmness. Here, bungalows glace out at the rustic bay while the feather beds (and dearth of alarms and clocks) allow unsurpassed tranquility and rest. Dine at the hotel’s eatery, Their dining room, overlooking Hana Bay and Ka’uiki Hill, that serves sumptuous fare (such as Hawaiian flatbread with Kalua pork, caramelized onion, and pineapple) and hand-crafted cocktails—before treasuring the starlit sky from your cottage’s private Jacuzzi.

Travaasa Maui


Day 5:


Start your east side day at The Spa at Travaasa Hana, Maui. Voted the #1 Resort Spa in Hawaii by Condé Nast Traveler, this plush but unpretentious spot provides head to toe pleasure.

Travaasa spa

Indulge in their ‘Ohe’o Forest massage, which targets specific muscle groups with the aid of organic bamboo and lime massage oil, round birch sticks, and hot Hawaiian stones. Traveling with your sweetheart? Book their couples’ massage, which includes an uber-healing scalp treatment, an herbal foot treatment, and a 90-minute full-body massage.


After bopping into Hana Fresh for an iced Aztec mocha and one of their super-delish salads (one to try: grilled pear with crispy prosciutto)—make your way to Hamoa Beach. With salt-and-pepper sand and groves of palms, this windswept cove is a great place to get your feet wet, sunbathe, and people-watch.

Next up? Seven Sacred Pools, where you’ll witness even more spellbinding sights. While the pools are presently closed, nothing will stop you from savoring their beauty from the sidelines, while Pipiwai Trail—a gentle hike, through a bamboo forest, that will take you to Waimoku Falls—beckons just beyond.

Charles Lindbergh

Whether or not aviation fascinates you, the location of Charles Lindbergh’s grave ought to inspire awe: Palapala Ho’omau Church is tucked into Kipahulu like a well-kept secret, offering dynamite views of Hana’s raw and wild coastline. Delight in the smell and sight of plumeria trees outside the limestone chapel before grabbing a souvenir at Laulima Farms and striking out for the Back Road to Hana—a serpentine, often-desolate route that boasts the most untamed, and untouched, parts of the island. Time it right, and you can watch the sun set off Maui’s southwestern coast. (Believe us when we say there’s nothing quite like it.)


Evening calls for more R & R—this time at the incredibly cozy Kula Lodge. Here, a botanical garden brimming with proteas and colorful flowers gives way to moonlit views of Maui’s outer islands. Dine near the fireplace in the lodge’s atmospheric restaurant, where you’ll find hearty eats (such as lamb chops with a red wine demi-glace and Molokai sweet potato hash), first-rate wines, and homey vibes. Savor an apres-dinner drink at the bar before exploring the gallery downstairs, which features Curtis Wilson Cost’s pretty, precise renderings of Maui’s pastoral jewels.

Kula Lodge


Day 6:


Following breakfast at La Provence—where you can splurge on lemon-cream crepes and a breve latte—cruise down to Makawao. Often touted as Maui’s paniolo town—a village that holds remnants of Maui’s cowboy culture—this small, eclectic settlement is a shopper’s paradise. And we’re not talking about big-box superstores and mall staples; rather, the boutiques here run the gamut from apothecary wonders (at Dragon’s Den Herb Shop) to high-end clothing (check out Hurricane and Oh, Baby!). Arrive early enough and you may be able to score some malasadas for later at Komoda’s—a hundred-plus year fave for Portuguese donuts. Slept in? Not to worry: Makawao’s Rodeo General Store peddles an array of sweet treats, as well as kefir, kombucha, and espresso.

Makawao Town


Make your way to the town of Waikapu, a modest establishment in Central Maui that once served as the hub of commerce during the sugarcane era. See evidence of this compelling, multi-ethnic past at Maui Tropical Plantation, a 60-acre working plantation that cultivates everything from coffee to papayas. Stop in at the plantation’s exhibits (presented by The Maui Historical Society) before heading towards the sky.

Maui Tropical Plantation

Aboard one of their zipline tours, that is, at Maui Zipline Company—one of the most family friendly and convenient on Maui. Circuits take intrepid travelers over fertile plantation grounds and some of Maui’s most hypnotizing valleys, and with many different lines, including one over the lagoon in front of the Mill House Restaurant, you’re bound to find a trip that’ll fit—or exceed—your personal edge.

zipline Maui


There’s something fantastic about sipping a locally crafted beer as the sun crosses the sky. Appreciate this feeling—which, let’s face it, feels like the epitome of a vacation—at Beach Bum’s BBQ & Grill in Maalaea, where boats will bob in the harbor as you sink your teeth into a Smokehouse Burger with bacon and jalapenos. Then hurry on over to Maui Golf & Sports Park, where you’ll be playing a sunset round of mini-golf before soaring thirty feet in the air on their X-Treme Trampoline. After all, who said kids get to have all the fun?

Maalaea Town


Day 7:


To underscore that last sentiment: Here on your seventh day, you’ll be spending your morning learning to longboard. Group lessons can be tons of fun, but a private tour will supply you with a touch more instruction on the nuances of hanging ten.

Maui Surf Lessons offer courses on the west side’s sparkling, temperate breaks, and, as one of the highest-rated surf schools in Hawaii, their team is determined to help you surpass your potential.


After lunch at Prison Street Pizza—where you can dig into a Jersey-style pie (like their Serpico with pepperoni, sausage, and peppers)—satisfy your yen for a dose of culture at the Wo Hing Museum. Built on the principles of peace, harmony, and prosperity, this temple and museum takes visitors back to Lahaina’s Chinatown of the early 1900s. With a bust of Sun Yat-sen (often referred to as the Father of Modern China) and heaps of fascinating facts, Wo Hing Museum offers a glance back at Maui’s intricate past.



Choose from five Top Maui luaus and experience what is frequently considered an absolute must on Maui for good cause: your evening entertainment provides another soul-stirring look at Hawaii’s complicated, astonishing past. Skilled dancers bring to life the formation of the islands, the myths that surround them, and the consequences of Western contact—and all of it is set to some of the most heart-thumping drum beats, chanting, and singing of any performance in Hawaii. And don't forget the fire dancing (our favorite part!)

Top Maui luaus

After the show, meander down to the Honua Kai, where you can walk the Ka’anapali Boardwalk to the Hyatt—and perhaps be talked into a sneaking into one of the luxe resort’s hot tubs.

Kapalua Trail


Day 8:


Grab a quick but healthy bite at Choice Health Bar in Lahaina before starting off your day quite literally on the right foot: The Kapalua Coastal Trail easily goes down as one of the most alluring strolls on the island.

Kapalua Coastal Trail

Running north from Kapalua Bay Beach, across Oneloa Beach, and to D.T. Fleming Beach Park, this mellow trek will allow you to take in the sound of birds and the vistas of Molokai—to say nothing of turtle sightings and the chance to pop into the glorious water. Start—and end—at Dragon’s Teeth, an outcropping of jagged black rocks that’ll remind you of Hawaii’s fiery history.


Golfing on Maui is near perfection: Immaculate, sun-dashed courses that are paired with magnificent views of the Pacific. And since you’ll be in the heart of golfer country—Kapalua is one of the leading golfing getaways in the world—why not go for a hole, or, rather, eighteen? Golf at Kapalua Resort is the definitive experience, presenting tee-timers with two superlative courses (plantation and bay) and a range of post-golfing lounging choices. (Check out Taverna for “urban” drinks, such as a Dr. Feelgood with Flor de Cana 7-year rum, St. Elizabeth All Spice Dram, and pink Hawaiian sea salt.)

Golf Hawaii


Hawaii Tasting Tours takes the idea of progressive dining to the next level: On this epicurean journey through Lahaina, guests meet at Fleetwood’s on Front St., where a spirited, knowledgeable guide will take you to a smattering of premier restaurants for samples of signature dishes, including prime rib from Lahaina Fish Co., hand-rolled pasta with kale and sausage from Sale Pepe, and fresh-veggie stirfry from Koa’s Seaside Grill. Accompanied by an educational foray into Hawaii and its burgeoning food scene, this is a terrific way to “feed” the 5 senses.

Fleetwood's Restaurant


Day 9:


Your last morning on the island ought to be spent reacquainting yourself with Maui’s exceptional natural landscape. Discover more of the island’s underwater wonders at Ahihi Kinau, a coastal reserve located near the southern, arid tip of the island. Surrounded by lava fields—and peering out at Molokini and Kaho’olawe—this cove of glimmering water is resplendent with reef creatures, including turtles, fish, urchins, and more. Snorkel to your heart’s content during the morning hours, when the lack of trades gives the water greater clarity (but, with its teeny stretch of sand and sublime views, don’t be surprised if you’re tempted to stay for hours).

Ahihi Bay

With all the beauty that surrounds you, it's a popular idea to book a Hawaii portrait shoot to capture these moments with your loved ones. We find many people like to take the photos then dip into the ocean afterwards (and sometimes durring!)


The Grand Wailea may be the polar opposite of nature—but that doesn’t render it any less spectacular.

Grand Wailea

Situated on 40 acres of first-class real estate, this enormous, exciting resort is often called Disneyland—but only if Southern California were so lucky. This may be appealing to some and not so much to others, but what remains is that the Grand’s pools—hands-down the best in Hawaii—are matchless, and provide a crazy-fun way to spend a sunny Maui day.

We’re talking a 2,000-foot long pool that includes seven tiers, rope swings that’ll awaken your inner Tarzan, rushing rapids, a water elevator (the first one in the world), a sandy lagoon, and a lazy river. With an adults-only hideaway, hot tubs tucked behind waterfalls, and bars that serve killer Pina Coladas, this is one of the most amusing and exhilarating ways to end your Maui stay.


But it’s not quite over yet, and if you’re still abuzz with energy, head to Kihei’s Island Art Party to commemorate your island holiday. Here, vivacious art teachers will provide you with the tools and instruction to paint a Hawaiian landscape—all inside a lively space hopping with happiness and bouncy music.

art party

Tending towards something more sedate, but no less fantastic? Watch your final Maui sunset (this time around) at the Four Seasons’ Lobby Lounge, an airy, seductive space that boasts hula dancers, live Hawaiian music, and brilliant views of the sun slinking beyond the horizon.


Conclude it all with an exquisite meal at Spago, where you can chow down on cones of spicy ahi poke and Thai style opakapaka while savoring views of the luminous water. Aloha ‘oe, as we say—at least until next time.


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