8-Day Maui Itinerary

October 7, 2019
Kaanapali Maui

The Beatles may be the first band to popularize the concept of eight days a week—and it sure sounds blissful, doesn’t it?—but it’s residents of Maui who are actually living the dream.

In other words, we know how to stretch out time so long it feels like we’ve been granted eight days a week.

8 days Maui itinerary


Happen to be coming to the island for the same amount of time? Here’s how to make like a Mauian and maximize every minute of your week-plus-one:


Day 1:



Haleakala Sunrise tour

Since your internal body clock is likely to be hours ahead of schedule anyway, you may as well make the most of your first morning on Maui by planning a visit to watch a spectacular sunrise atop the world’s largest dormant volcano, Haleakala.

While some visitors opt to drive themselves, the winding, uphill journey in the dark is somewhat tedious, so we recommend the much more relaxing approach of a guided Haleakala Sunrise Tour, which includes round trip transportation from your hotel – a treat when your pickup time is somewhere between 2am and 3:30am – as well as snacks, warm drinks to enjoy at the summit, and a full buffet breakfast on your way back down. The guides are well versed in fascinating commentary on the local history and culture of the area, and the panoramic views from the comfort of a cozy leather seat certainly make for an unforgettable first morning on Maui.

To ramp up your adventure level and get the most out of your early morning wake-up call, we also recommend combining your tour to include a post-sunrise, 21 switchback downhill bike ride, continental breakfast and 5-line zipline experience as part of the Haleakala Sunrise Bike & Zip tour from Skyline Hawaii. Round trip transportation is included, and guests must be at least 12 years old and weigh between 60 and 260 pounds. Hey, if you’re going through the effort to experience the magic of Haleakala, this combo tour offers a 3-in-1 opportunity for further exploration.

top tours haleakala mauiFirst, the facts.

Haleakala is a well-trod destination for a reason. Climbing 10,023 feet into the sky, it looms above Maui like a premonition. Deep within its 3,000-foot crater rests an alienesque landscape comprised of lava tubes, caverns, and cinder cones. Up above, Hawaii’s state bird—the endangered nene goose—trundles by the Haleakala silversword, a surreal, majestic plant that grows nowhere else on Earth. Meanwhile, Maui’s golden coves shimmer below the clouds and the quiet stretches on for miles.



Following lunch at Kula Bistro (try their Kalua Pork egg rolls for a taste of Hawaii), make your way to Lumeria Maui—an upscale resort and healing center on Makawao’s verdant slopes. Here, you’ll be giving your muscles major relief with Lumeria’s signature crystal massage. Inspired in part by the four life forces in Hawaiian culture, this profoundly restorative treatment includes aromatherapy oils, Lemurian seed crystals—and hands well-versed in therapy.



Charley's Maui

Nuka makes sushi ultra-seductive at their glossy little spot in Haiku. Here, consummate sushi chef Hiro Takanashi delivers delectable sashimi and innovative rolls, such as the Hawaiian with ahi, avocado, and roasted macadamia nuts.

Then, sling back a shot of espresso from Paia’s Honolulu Coffee before strolling into Charley’s Restaurant and Saloon for a nightcap. Widely renowned as North Shore rez Willie Nelson’s favorite watering hole, this bluesy-but-beachy bar is often abuzz with fun. Have as much as you’d like: Given that you’re staying at the super-hip Paia Inn nearby, you can walk—or crawl—to your bed.


Day 2:



Paia and Kuau

There’s nothing like being the first footprints on the beach, something you can readily accomplish by using daybreak to amble down to Kuau Cove—a picturesque stretch of sand just past Paia. Explore the tide pools and go for a dip—a dose of Vitamin Sea will pump you up with energy.

After your swim—and a plate-full of cardamom French toast at your hotel (whose staff, by the way, was ranked among the “World’s Sexiest” by Condé Nast Traveler)—take an hour or two to browse the windsurfing capital’s boutiques and galleries. A few musts? Puka Puka, a chic shop on Paia’s western end; here, you’ll find organic surfboard wax, surf art by Jim Severson, and custom boards. Meanwhile, Alice in Hulaland peddles hip shirts that could double as décor, Indigo Paia displays portraits of photographer Daniel Sullivan’s travels, and Maui Crafts Guild showcases work exclusively by local artists.




It makes perfect sense that Twin Falls lures a sizable crowd to its crown jewels. The waterfalls, which are part of Ho’olawa Valley, are fantastic. It’s minutes away from Haiku, rendering an afternoon here less of a commitment than a drive to Hana (although, mind you, that is in our itinerary). And the hike to reach the falls—through the lush grounds of Wailele Farm—is heart-pounding pretty.  Check out Hike Maui for guided trips to the private waterfalls at Twin Falls.

Peahi, Maui, Hawaii

Fronted by acres and acres of a former pineapple plantation, Peahi—whose apt translation means “wave” in Hawaiian (as in, to beckon)—began entrancing more than Hawaiians and kama’aina in the early 90s, when big wave surfers Dave Kalama and Laird Hamilton started surfing its enormous, unpredictable swells.

And enormous they are: From December to May, waves that reach the 30-foot, cone-shaped ridge on Peahi’s seafloor turn into beautiful monstrosities that peak at 60-plus feet—and rev for up to 200 yards. Whether or not you happen to be visiting during this time, stop between mile markers 13 and 14 to see the raw and unshakable forces of the ocean.



Grab a famous maitai at Mama’s Fish House or save some cash and have a great meal in Paia at Cafe Des Amis where they serve delicious savory crepes and other Mediterranean dishes.  Ask for their lilikoi margarita.  AMAZING!

North Shore Maui restaurants



Day 3:



snorkeling Maui

Maui’s marine life is incomparable. The clear, dazzling water banking our shores teem with a cornucopia of aquatic creatures, from Hawaiian Spinner Dolphins and manta rays to Hawaiian Green Sea Turtles and moray eels. What’s more, Humpback whales (aka 45 tons of magnificence) migrate from Alaska to Hawaii from November to May. One of the choicest ways to see them (and the rest of Maui’s ocean animals) is with a Maui snorkel tour.

You have 2 choices: take a big double-decker catamaran or smaller raft. Aboard speedy but safe rafts, groups are very small, meaning you and your crew are in for a special, private tour of Maui’s gorgeous waters. Half-day snorkeling excursions—complete at approx. 5 hours—takes visitors Kihei Boat Ramp, Maalaea Harbor or Lahaina Harbor to two to three snorkeling outposts, where a guide will give you the goods on our tropical wonders while you splash in and out of the water.



While Hawaii Ocean Rafting’s half-day tour includes a continental breakfast, snacks, and beverages, all that fun in the sun is sure to spur an appetite. Indulge yours by digging into some local eats at Aloha Mixed Plate. Set on the oceanfront in Lahaina, this bright, lively place serves up some serious chow, from Kalbi ribs to coconut prawns.

Once you’ve had your fill, grab some shave ice—the iconic treat of Hawaii—before joining forces with Maui Nei. Helmed by a kumu (or local guide), this walking tour will take you on a fascinating expedition of the former capital of Hawaii, which, over time, has transformed from a missionary village to a whaling port to a plantation—to its status now as a world-class destination.



Lahaina Maui

Warren & Annabelle’s—an unsurpassed magic and comedy show in downtown Lahaina—sells out nightly. No surprise there: This is a Maui favorite. Here, acclaimed showman and one of America’s leading sleight-of-hand magicians, Warren Gibson, pairs up with a piano-playing ghost to knock your socks off (or, rather, your slippahs and watch). His interactions with the audience are downright delicious, but it’s the tricks and wit of this dynamite show that will you with grinning and breathless.


Day 4:



For the uninitiated, paragliding might seem exclusively reserved for daredevils. But given the reputation that paragliding has earned as the safest and simplest form of personal flight, it’s since become more mainstream. Hop onto the bandwagon—and test your personal boundaries—with a paragliding tour from the slopes of Haleakala. The bird’s eye view will astound, while the full-body experience will leave you electrified.



Upcountry Maui Hawaii

Upcountry Maui is a world of its own—a place where rolling hills give way to panoramic vistas and unusual fauna (think: jacarandas and eucalyptus) scent the misty landscape. Within this idyllic haven rests Ulupalakua Vineyards, where you can sample pineapple wines while peering down at the mesmerizing coastline. Lunch at Grandma’s Coffee House in Keokea; the intimate, laidback café offers some of the best baked goods on the island. Pop into the gallery next door to get an eyeful of John Sheldon’s Wallau’s surfboard art, and then spread out a blanket in Keokea Park. With its serene surroundings and outstanding views of Haleakala, this is the way to revitalize after such an exhilarating morning.



Makawao presents another side of the Valley Isle—one that speaks to Hawaii’s vaquero past and the paniolo culture that developed after the arrival of horses. While the town is now more gentrified (it’s considered one of the best places for artists in the country), its cowboy soul remains—and can be found quite poignantly at the village’s eponymous steakhouse. Select a choice cut, pair it with a robust drink, and enjoy the blaze in the homey fireplace.

For a nightcap you won’t soon forget, head back down to sea level to give Wailuku’s Mystery Maui Escape Room a try. Set in one of two cleverly-designed escape room scenarios, private groups of 2 to 6 people will team up to solve the mystery and escape their given room in 60 minutes or less. With help from your game marshal, you can put on your best Sherlock cap to unlock the clues in front of you, and discover new ones along the way. A budget-friendly and extremely fun way to end your night on The Valley Isle, we particularly love talking story with the friendly owners and working our way through a totally unique escape room scenario you won’t find anywhere else on earth.

maui escape rooms


Day 5:



Maluaka Makena

Wailea—a stunning enclave on the south shore of the island—is about far more than tony golf courses and equally tony resorts (although both are mad enjoyable): This sunny stretch boasts several of the top swimming holes on Maui. Makena’s Maluaka, in particular, is one for the records; here, sugary sand is framed by quintessential palms while Kaho’olawe and Molokini gleam in the distance. The water, meanwhile, is clear as glass, rendering snorkeling, swimming, and body-boarding terrific (and a total blast).



Makena snorkeling

Grab lunch at Bubba’s Gourmet Dog Shack just up from Maluaka on Makena Road, and then hit up more of the island’s rugged southern flank. At One’uli, you’ll find a cove of tobacco-shaded sand, where the views of Pu’u Ola’i—a cinder cone created by Haleakala’s last eruption—are nothing short of spectacular. Check out the tide pools on the beach’s northern end, where urchins and sea cucumbers shimmy in the water.

Then, head out to Ahihi Kinau Natural Reserve, where you can put your snorkel mask and fins to even greater use. Rightfully deemed a leading snorkeling spot on the island, the fish here are wild and profuse, including the beloved humuhumunukunukuapua’a.



Wailea Maui

Call it a safari supper. A round-robin. A trip in taste. No matter: the point is that progressive dinners are a delightful way to experience the best a region has to offer.

Lucky for you, Wailea has bloomed into one of the top culinary hubs on the island. Start on the northern end of its strip of resorts, where the masterminds at Ka’ana Kitchen plate out wicked-good pupus that range from grilled octopus with Big Island chevre to a watermelon salad with candied walnuts. Ready for more? Meander towards your main meal at Humble Market Kitchin in the Marriott next door. Here, Roy Yamaguchi—a preeminent Hawaiian chef and the brains behind 30 Roy’s restaurants throughout Hawaii and Guam—delivers ono eats, such as a hot-iron seared “kale kale” (lavender snapper) with fennel and saffron fumet. Pause for a post-dinner stroll along the Wailea Coastal Walk—where the lulling waves and luminous stars reinforce the fact that you’re in paradise—before heading to Ko for Portuguese sweet bread with coconut gelato, vanilla sugar, and Kula-grown black raspberry jam.


Day 6:



Maui helicopter tours

Maui Helicopter tours have been flying valiant voyeurs to Maui’s most secluded gems since 1985. As the only air tour company to serve the whole state, Blue Hawaiian provides the kind of thrills that are genuinely inimitable. Relish a fresh perspective of the island from the cabin of their quiet and comfy EcoStar ‘copters, which will plunge into the astounding verdure that is Honomanu Valley and soar above Haleakala’s crater floor. This is the Maui few see—and the Maui that’ll get deep into your heart. Call (808) 871-8844.



Maui Ocean Center

Maui Ocean Center is Hawaii’s premier in-door activity: As the largest tropical aquarium in the Western Hemisphere, it features a 750,000-gallon tank packed with deep-water wonders, including tiger sharks, honu, and stingrays. With a 54-foot walkthrough tunnel and the planet’s biggest collection of live coral, this oceanic wonderland instructs, awes, and inspires.



Slack key originated in Hawaii in the 1830s when vaqueros were brought to the islands to teach natives how to lasso, brand, and ride. Evenings then were spent in literal harmony: The Spanish cowboys would pull out their four-string basses, six-string catguts, and four-string tenors to make some killer melodies. When the vaqueros’ contract ended, they left behind several of their instruments—including one that was picked up by George Kahumoku Jr.’s grandfather, who, with other native Hawaiians, slackened the strings to “open” the tunings—thus giving rise to one of the loveliest and most soothing sounds to ever be produced by a guitar.

Today, that tradition is carried on by Kahumoku Jr. himself, who, as a Grammy Award winner (and the “Hawaiian Renaissance Man”), showcases his heritage every Wednesday night with his Slack Key Show: Masters of Hawaiian Music at Napili Kai Beach Resort. Start with dinner at the Sea House Restaurant (where you can dive into a mixed grill with fresh fish in lemon beurre blanc, shrimp scampi, and petit steak) and then cruise over to the Aloha Pavilion to see some of the grooviest fingerstyle acoustic guitar around.


Day 7:



Road to Hana tours

52 miles. 617 curves. 54 bridges. Getting to Heavenly Hana is in itself an adventure—particularly since all of it is paired with sights too exquisite for words (dense rainforests, towering waterfalls, black sand beaches, magnificent sea cliffs, and quilted patches of taro). Navigate the road yourself, and you’re free to stop wherever (and whenever) you please, but as your guide to Maui, we advise spending your morning hours over a Maui cattle-Loco Moco breakfast at Café Mambo in Paia. Then, hit the twisty, spellbinding road, where your next major stop should be Wai’anapanapa State Park. Here, 122 acres are filled with one natural marvel after another, including beguiling lava tubes, an astonishing rock arch, an onyx-sand beach, serrated rock cliffs, and a peaceful seabird sanctuary. Keen on having an authority man the car—and show you the scenery? Book a journey with one of Maui’s premier tour companies; Road to Hana Tours, for one, is tops.

road to hana best toursAlternately, Rappel Maui offers a slightly more daring way to experience the Road to Hana from a whole different perspective. With no previous rappelling or climbing experience necessary, their daily Classic Canyon Rappelling Tour is open for guests 10 and over, and weighing at least 70 pounds. After driving to their central Maui meeting point, you’ll be transported half way through the Hana Highway before arriving at a 30 acre botanical garden, where you’ll gear up and walk to the first stop – a 60 foot dry jungle wall – for your initial rappelling practice run. Afterward, you’ll continue onto a 50 foot waterfall and 30 foot waterfall, where you’ll perfect your rappelling skills while enjoying the gorgeous jungle scenery around you. Take a dip in a natural swimming hole and rest easy knowing your safety (and fun!) is a top consideration. Tours last approximately 6 1/2 hours and a catered lunch is included.



Travaasa Hana

You might be on one of the remotest coasts on Maui, but that doesn’t mean you won’t find elegance—and excellent (albeit limited) dining options. The Travaasa Hana, Maui presents first-rate eats at their inviting restaurant, The Preserve Kitchen + Bar; here, you can linger over a lovely meal sourced from local farms. Go for their seasonal spicy greens (which is made sweet with papaya seed dressing) and savor the views of Ka’uiki Hill, a myth-steeped cinder cone where civic leader—and King Kamehameha’s favorite wife—Queen Ka’ahumanu was delivered into the world.



Oheo Gulch

Kipahulu—a sustainable farming community about eleven miles past Hana—may be part of Haleakala National Park, but it’s starkly different from the barren crater that gave it its official moniker. Once a largely populated agricultural hotbed, the chill, beautiful district is now home to boutique farms, aviator Charles Lindbergh’s grave, and a few celebrity residents.

Its real star, however, is Ohe’o Gulch. Otherwise known as Seven Sacred Pools (a misnomer, given that more than seven waterfalls cascade down these parts), this extraordinary park features freshwater pools and dramatic rock carapaces—and all of it is surrounded by dazzling greenery and views of the vast Pacific. Check ahead to see if the pools will be closed (the park has recently been shuttered, due to rock slides, flash floods, and accidents); if so, cross the street to Pipiwai Trail, where you can make the most of what’s left of the day to trek through a bamboo forest to the 400-foot Waimoku Falls.


Day 8:



Kaanapali Beach

Beat the blues that tend to arrive at the end of a holiday by absorbing the splendor of Ka’anapali Beach—a three-mile stretch of immaculate sand bordered by luxe resorts and views of Moloka’i. Grab some 100% Kona joe at Island Vintage Coffee—a charming café tucked into the adjoining Whalers Village—swim out to (or leap off) Pu’u Keka’a, or just spread out a towel and bask in the brilliance—there are few better feelings than simply soaking up the Maui sun.



Devote the better half of your morning to hovering above the skyline. This time, however, it’ll be astride two cables as you whiz above the West Maui Mountains with Kapalua Zipline. With a seven-line tandem zipline, this excursion will take you on a Polaris ATV ride before sending you over two miles of luxuriant jungle—and a scenic, seasonal waterfall.



Sheraton luau Maui
No trip to Hawaii is complete without a luau. While there are a number of stellar performances from which to choose, the Maui Nui Luau at Black Rock gives the ancient celebration an innovative twist: watch the torch ceremony before the torch lighter jumps off the cliff at Black Rock.  Then the Sheraton Luau Maui presents a luau feast buffet extravaganza that highlights the primary islands of Polynesia. Accompanied by traditional dances and chants, this intimate, family-friendly event is much like Maui itself: impossible to forget. Eight days have never felt so good, have they?

Blog Comments

Awesome, Thank you! Going to Maui in November. This will help lots!

Going in November….I just had surgery so no zip lines for me. Will I still be able to see waterfalls and Beautiful places?

Certainly hope so! What kind of surgery?

I’d love to see how much all of this would cost if you followed this itinerary! $$$$$$$!!!!! Unrealistic.

It’s definitely not for every budget. We’re also not saying you have to do everything on the list. That being said, this is a great itinerary for Maui!

Maui is beautiful but crime is out of control along with the homeless population. Everywhere you turn, in every public beach park, there are homeless and tent cities. Never leave anyting in your car or you windows will be busted out when you return. Also, I found that most Hawaiians do not like tourists. We began to feel that “mahalo” really meant “get over it.”

So sorry to hear about your experience! We’ve lived here most our lives and have had our window broken and stuff stolen once. I rarely see homeless on the beaches.

great stuff..been doing maui long time, but your suggestions are right up there.
thanks and aloha
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