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. Enjoy this 8-day Maui itinerary.
Before we dive in… the real question is, where should your home base be for your eight blissful Maui days? Consider the Fairmont Kea Lani in Wailea, where bland, cramped hotel rooms are swapped for sleek suites and villas. This resort has a secluded feel while conveniently located near some of our favorite Maui beaches, restaurants, and activities.
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:
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, Haleakalā.
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 2 am and 3:30 am – 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.
If you are not into sunrise, they also offer a sunset tour. Also, if you want to take your Haleakala experience to a new level, try a morning bike ride down the volcano. Tour Upcountry Maui on a downhill bike ride where you will do more braking than pedaling while you take in unbelievable views of Mauiʻs central valley and surrounding islands of Kahoʻolawe, Lanaʻi, and Molokai.
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.
After your morning adventure, it will be time to eat! Head to Kula Bistro (try their Kalua Pork panini for a taste of Hawaii) for lunch. Then 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.
Grab some takeout pizza and head for sunset at Paia Bay. Restaurant Marlow has quickly made a name for itself as the best pizza on Maui with woodfired sourdough Neapolitan-style pizzas. Grab some meatballs and try the octopus too!
For those willing to get there early and save sunset for later, it’s worth getting a table for the full experience, then heading next door to Mahalo AleWorks for a pint or 2. The sunset from the Mahalo patios is awesome!
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, head to Paia Town and take an hour or two to browse the windsurfing capital’s boutiques and galleries. A few musts? Soley Aloha Boutique is a family-owned and operated shop on the west end of Paia specializing in men’s, women’s, and kids’ apparel, jewelry, and other accessories. They also feature local art and photography, and shopping here is a great way to support a local family. 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.
Next, make the 20-minute drive to Haiku Town – Paia’s lush, sleepy neighbor. This small town is known for its smattering of cafes and restaurants (like the esteemed Nuka Sushi) and niche shopping opportunities like Ace of Cups.
Haiku is known for its supernatural energy, and Ace of Cups capitalizes on the magic of this north shore town. This witchy divination shop specializes in tarot and oracle decks from around the world – some decks are ultra-rare, while others are designed right here on Maui. The shelves are also stocked with crystals, pendulums, journals, oils, sprays, and books on tarot and astrology. Stop by at the right time, and you can get a reading by one of Maui’s tarot, akashic, or astrology experts. Check out @ace.of.cups.maui on Instagram for reading and workshop schedules.
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.
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 kamaʻaina in the early 90s when big wave surfers Dave Kalama and Laird Hamilton started surfing its enormous, unpredictable swells. Due to the size and unforgiving nature of this wave, it has become known as ʻJawsʻ.
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. Getting down to Peʻahi can be difficult and sometimes dangerous and is not recommended unless the waves are breaking (check the surf report to see what is happening at Peahi before making the journey). Please take precautions and err on the side of safety when visiting this area. You will also be in a local neighborhood, so please show respect to the people and the land.
Grab a famous mai tai 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!
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) return home from their feeding adventures in 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 a 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. Snorkeling tours typically begin in the morning when conditions are calm and usually take up about half the day. Half-day snorkeling excursions— approx. 5 hours—takes visitors from Kihei Boat Ramp or Maalaea 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. One snorkel tour that has our attention is with Island Star. You’ll find yourself enjoying an intimate yet luxurious 57-foot sailing yacht from Maalaea Harbor to Lana’i. Limited to 18 passengers, you’ll snorkel some of Lana’i’s most secluded reefs and look for dolphins and whales (in season.)
While Island Star’s 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 fresh island seafood at Seascape Restaurant. Set along Maalaea Harbor, this bright, lively place serves up some serious locally sourced chow, from fresh fish and vegetables to Kauai prawns.
Once you’ve had your fill, grab some shave ice—the iconic treat of Hawaii—before heading to the Maui Tropical Plantation for your next adventure, a botanical garden tour. The Maui Tropical Plantation is home to a bevy of native Hawaiian flora, tropical flowers, and beautiful scenery. Take the tram tour for an in-depth breakdown of the grounds and what they are growing. For the daring, take a zipline tour of the plantation and see the farmland from above.
Cafe O’Lei at The Mill House is the restaurant set within the gardens at the Maui Tropical Plantation and is a perfect spot to celebrate another great day on Maui. With amazing views of the pond and up into Waikapu Valley, the sunset will be coming soon and that will paint some nice colors in the sky as a backdrop to your evening. Try some of the locally inspired dishes, hand-crafted cocktails, and desserts while you relax and reflect on your day.
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 is a world of its own—a place where rolling hills give way to panoramic vistas and unusual flora (think: jacarandas and eucalyptus) scent the misty landscape. Within this idyllic haven rests Maui Wine, where you can sample delectable 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 shops and restaurants. Do your best to check out Hot Island Glass before they close at 5 pm to see some beautiful artwork. Then walk to one of the restaurants in town.
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.
Wailea—a stunning enclave on the south shore of the island that is about far more than golf courses and resorts (although both are madly 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).
If you decide to participate in any water activities, be sure to check out the Maui Snorkel Report for the most up-to-date information about snorkeling conditions and recommendations at various spots around Maui.
Grab lunch at Jazzy’s Beach Kitchen or Jawz Tacos 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.
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 (Andaz) 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 (Fairmont Kea Lani) for Portuguese sweet bread with coconut gelato, vanilla sugar, and Kula-grown black raspberry jam.
Maui Helicopter Tours have been flying valiant voyeurs to Maui’s most secluded gems since 1985. These heli tours provide 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 beaches, waterfalls, sea cliffs, and volcanic coastline. This is the Maui few see—and the Maui that’ll get deep into your heart.
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 ever to 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 guitars around.
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 Loco Moco breakfast at Paia Bay Coffee Co. in Paia. Then, hit the twisty, spellbinding road, where your next major stop should be Wai’anapanapa State Park (reservations required). 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.
You might be on one of the most remote coasts on Maui, but that doesn’t mean you won’t find elegance—and excellent (albeit limited) dining options. The Hāna-Maui Resort presents first-rate eats at their inviting restaurant, The Restaurant at the Hāna-Maui Resort; 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.
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, the 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. The pools are permanently closed for swimming but a 1 mile loop trail brings you down to the bottom pools for some photo opportunities. Next, 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. Head back to your hotel after this for some much-needed rest.
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 six-line side-by-side zipline, this excursion will take you on an ATV ride before sending you over two miles of the luxuriant jungle—and a scenic, seasonal waterfall.
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?
Want more than 8 days?
Considering that it’s more than likely that you have found yourself deep in the throes of a passionate love affair with this little island, why not indulge yourself in a house hunt? There are a number of properties currently listed on Maui, from vacant lots to luxury homes to humble condos. Spend an afternoon on the best type of island tour – a house hunt. Maui realtors will help you find the property most suitable for you so that you can turn eight days on Maui into an eternity.