10 Day Maui Itinerary

Ten days in the tropics might sound like a lifetime when you’re toiling away for that trip, but arrive on Maui and you’ll find that island time is far from just a myth.

10 Days Maui itinerary
10 Days Maui itinerary

10 Day Maui Itinerary

Whole days can disappear in such blithe, beachy bliss that your entire vacation can pass by in the blink of an eye. Prepare to relish every minute of your hard-won break with this ultimate guide to your ten-day stay:

Day 1: Get Pacific

ocean snorkleing
ocean snorkleing

As in tranquil, valiant traveler. The best way to slip into the aloha rhythm is to make like a local and head straight for the beach. Jetlagged mornings call for stretches of barely-trodden sand and surf so calm you can get lost on its surface for hours. The farther south you drive, the quieter your respite, with Wailea’s Polo Beach and Makena’s Third Entrance representing everyone’s need for some serious R &R. Post-swim, grab some grub at Kono’s on the Green—they serve a mean Kalua pork sandwich with tangy mango slaw and crispy Maui onions.

Legs feeling restless from your flight? Take an afternoon stroll along Wailea Coastal Walk, a 1.5 mile boardwalk that runs parallel to the sea and takes you past the glistening beaches that made this enclave famous.

Then, carry the aquatic theme to its logical end with a sunset dinner cruise with the Pride of Maui, a luxury catamaran that serves up delicious eats with even better views.

South Maui
South Maui

Day 2: Scale and Soar

jaws Peahi
jaws Peahi

Spectacular reaches whole new heights when witnessing the sun rise from the lip of Haleakalā Crater. The loftiest dormant volcano in the world scrapes the sky ten thousand feet above Maui’s gorgeous shores, where dawn breaks open the Daliesque sky in epic columns of rose, lavender and gold. Rise early to celebrate the spectacle and then sail down the crater’s mist-smoked slopes with Haleakala Bike Company, an outfit that lets you set your own pace.

Stop for lunch when you hit sea-level: Paia—the “Windsurfing Capital of the World” and a hip, vibrant village—boasts a number of prime spots, from Mana Foods fresh, wholesome choices to Hana Ranch Provisions delectable island dishes. Shops and galleries spanning from funky to posh fill the main drag of this whimsical town, guaranteeing that you’ll find more than one souvenir worthy of that extra weight in your luggage.

Prior to your day’s end, take a jaunt to Ho’okipa Beach Park, where Hawaiian Green Sea Turtles splash in the waves and bask on the rocks at dusk. Then venture east towards Peahi. Otherwise known as Jaws, this is where world-class surfers show off moves that bring new meaning to the notion of riding high.

Haleakala Paia
Haleakala Paia

Day 3: Catch Some Perspective

helicopter Maui
helicopter Maui
Island art Party and food trucks
Island art Party and food trucks

With its plethora of sensory pleasures, Maui makes the concept of hedonism seem mild. While there are few feelings lovelier than its warm sand between your toes, the island takes on a completely new level of decadence when seen from the skies above. Blue Hawaiian Helicopters takes thrill-seekers to parts of the Valley Isle that can only be accessed by air or imagination—from waterfalls in fabled Hana to gem-toned cliffs in the West Maui Mountains.

With that newfound appreciation for the island’s ‘aina, seek out some local eats when you touch down on land. Wailuku’s iconic Tasty Crust has been dishing out homey faves since their inception in the 70s (don’t miss out on their legendary banana pancakes), while Kahului’s food trucks offer fresh, ono grinds.

Feeling hoppy? Get your evening started with a proper pau hana at Maui Brewing Company, a modern, airy venue that pours handcrafted ales from around the isles. Try the La Perouse White Witbier, a killer creation that pays homage to the southern side’s beguiling coast—or a thick IPA that self-explains its Big Swell name.

Buzzy or not, don’t let that artistic inspiration you gleaned from your tour go to waste. Kihei’s Island Art Party gives guests a chance to discover their inner Picasso with simple lessons from seasoned instructors. Want to keep the party going? Beer, wine, and bubbly are served, along with complimentary popcorn.

Day 4: Dive In

Black Rock Maui
Black Rock Maui
Warren and Annabelle Lahaina
Warren and Annabelle Lahaina

Long before Kāʻanapali's shores shone with gleaming hotels and sand-bottomed restaurants, its western edge, Pu’u Keka’a—otherwise known as Black Rock—was considered a sacred spot where ancient Hawaiians leapt into the realm of spirits. Now, the favorite among locals and visitors alike is the site of dives into the very physical world of the warm Pacific, where tropical fish cartwheel through the calm, lucid water. Take a swim or brave it with a jump; either way, you’ll understand why this was named one of Hawaii’s most beautiful beaches. (And trust us: The competition is fierce.)

Looking for a little history? Stroll on over to the Whalers Village Museum, a bright, fascinating space that pays tribute to the 12,000 Humpback Whales that migrate to Hawaii annually. Boasting one of the largest scrimshaw collections in the world, this brief but illuminating tour just off Kāʻanapali Beach will have you saying “Call Me Ishmael” until the sun meets the sea.

West Side nights are best spent taking advantage of some of Maui’s greatest entertainment. Chief among the island’s top dinner performances is Warren & Annabelle’s Magic Show, a four-hour extravaganza of swills and sleight-of-hand thrills—all of it led by showman extraordinaire Warren Gibson and his ghost of a piano-playing sidekick, Annabelle.

Day 5: Green and Bare It

Iao Needle on Maui
Iao Needle on Maui

Slicing into the sky at a most uncommon angle, Iao Needle goes down as one of the island’s rarest and most mystical spots. Home to the infamous Battle of Kepaniwai in 1790—a fight that led to the unification of the majority of the Hawaiian Islands—this stream-centered park now houses verdant walking paths and stunning views of the central valley. Climb the steps to near closer to the lush rainforests that canopy the jade and sage-hued cliffs.

Just a short jaunt away from Iao stands Maui Tropical Plantation, as iconic to the Valley Isle as Diamond Head is to Oahu. Spanning sixty fertile acres filled with crops that range from jack fruit to kale, this working-plantation offers curious minds a taste of what it means to live off the ‘aina. Tram tours take guests through land ripe with plumeria and papaya, while their zipline rockets flyers over technicolor fields and ahupua’as. The plantation’s Bailey Historical House offers a thrill of a different kind, guiding guests through Waikapu’s nuanced history. And don’t miss a stop at their Roasting Café, where 100% Maui-made coffee is brewed with utmost skill and flair.

Maui Tropical Plantation
Maui Tropical Plantation

No trip to Maui is complete without an evening at The Mill House, our dazzling new restaurant on the plantation’s storied grounds. Here, award-winning chef Jeff Scheer takes direction and inspiration from the plants peaking just outside his kitchen’s doors, delivering to guests tapas and desserts that range from coffee-cured beetswith farm-fresh fennel to pineapple citrus pie with macadamia nuts and sage. Signature cocktails get an innovative island spin, while outdoor seating provides exquisite mountain views found nowhere else on the island.

Day 6: Escape Down Under

Thanks to its iridescent water and thriving coral reefs, Maui is consistently ranked one of the leading spots in the world for snorkeling. The sun-swept south shore supplies some of the most impressive diving and snorkeling sites on the island, with Ahihi Kinau scoring extra points for its warmth and serenity. Stop by Boss Frog’s on your way: They offer daily gear rentals and terrific insider tips.

Maui Ocean Center
Maui Ocean Center

Intrigued by the island’s majestic marine life? Journey to Maalaea for a tour of the wonders housed at Maui Ocean Center. Home to the largest collection of live Pacific corals in the world, Maui Ocean Center—voted one of 25 best aquariums in the US—offers lively presentations, behind-the-scenes tours, and the only shark diving activity on the island.

Head west before the sun descends to steep yourself in Hawaiian culture. Old Lahaina Luau transports guests to another era, where storytelling was rendered in song and hula spoke its poignant language. Located on the island’s mesmerizing West Side, Old Lahaina Luau’s traditional feast provides guests a taste of ancient Hawaii. Imu-roasted Kalua Pork and fresh-caught fish take center stage, while chicken long rice, lomi-lomi salmon, and haupia comprise just a few of the Imu-roasted Kalua Pork and fresh-caught fish take center stage, while chicken long rice, lomi-lomi salmon, and haupia comprise just a few of the ho’olaule’a’s excellent sides.

Day 7: Roam and Ride

Break away from the beach crowd and assume a new rhythm on Maui’s pastoral upper slopes. Ali’i Kula Lavender Farm presents an entirely different part of the Valle Isle, where lilac fields studded with protea and hydrangea spill towards picturesque views of the ocean 4,000 feet below. With 45 varieties of this mauve, hypnotic plant, guided walking tours are offered daily, while keiki can get lost in the purple haze on the much-loved Lavender Treasure Hunts. Slip into their gift shop to stock up before you depart—from soy candles to gourmet seasonings, this sweet boutique offers a handful of ways to let that soothing scent linger.

Lavander flowers
Lavander flowers
Upcountry Zipline
Upcountry Zipline

Take in the breathtaking views as you meander down the mountain towards Makawao, a laidback outpost that moves at its own clip. With specialty spice shops that share walls with trendy boutiques, Makawao is perfect for both window shoppers and big spenders alike. For a lunch loaded with flavor, step into Rodeo General Store. Items like ahi poke, sushi, and biscuits and gravy make it known that this corner grocery is only quaint in name.

Ready for a shot of adrenaline? With 6,400 feet of ziplining, Piiholo Ranch Zipline takes intrepid travelers over lush gorges and through a forest of immense, otherworldly trees. Soaring above the jungle floor, you’ll understand why this exhilarating ride is frequently named one of the first-rate activities on the island.

Delight in a dinner under chef Bev Gannon’s direction at Hali’imaile General Store, where her plantation store-cum-restaurant plates up award winning dishes that span from crab-topped pizza topaniolo ribs. Splurge on dessert before swinging back towards your hotel. Their lilikoi brulee withalmond brittle is as luscious as it is crisp.

Day 8: Witness Some Wonder

Stand up paddle
Stand up paddle

One of the splendors of life on the Valley Isle is kicking it on the beach and seeing whales breach mere yards offshore. But if you’re determined to see that iconic tail surface from the sea, don’t rely entirely on serendipity. During whale season—which starts in November and ends in May—the Kai Kanani gives guests an intimate view of one of the Pacific’s largest and most captivating creatures.Marine naturalists make up part of the crew, offering sightseers rich information on this beautiful baleen and its vital Hawaiian habitat.

Back on land, explore the ocean on your own with private SUP lessons from Hawaiian Paddle Sports. Deemed one of the most popular sports in the islands and beyond, seafaring students can adjust their own pace to match their moods—whether it’s a vigorous workout or a leisurely glide to admire the vistas of the outlying islands. Daily tours to Makena’s aptly-named Turtle Town take pupils within close proximity of Maui’s sweet tempered honu.

Balmy island evenings are best paired with equally-sultry music. Venues abound around the Valley Isle, from Grammy nominee Willie K’s weekly performances at Mulligans on the Blue in Wailea to IZ-inspired remakes at Nalu’s South Shore Grill in Kihei. Planning ahead? Check out the upcoming shows at the Maui Arts and Cultural Center, which attracts an eclectic mix of choice entertainers from around the globe.

Shows in Maui, Hawaii
Shows in Maui, Hawaii

Day 9: Roll In the Deep

Many visitors to Maui can hardly get enough of the island’s underwater wonders. Relish even more of its treasures by sinking beneath the waves aboard the Atlantis Submarine. This state-of-the-art vessel carries voyagers over 100 feet beneath the Pacific’s glassy surface, where lustrous fish and grinning rays cruise through the crystal-clear water.

Submarine Maui
Submarine Maui
Ulalena Lahaina
Ulalena Lahaina

Then, take advantage of your West Side day by exploring the dynamic streets and beaches of Lahaina. The former capital of Hawaii, missionary town and whaling mecca is now home to the world-renowned Front Street, which features oceanfront galleries, shops, and restaurants (as well as the largest banyan tree in the US). Hunting for sun-touched celebs? Mick Fleetwood’s eponymous eatery boasts an awesome lanai, while Hard Rock Café sees a fair share of familiar faces darting through its doors. Those searching for a feast for the eyes need to look no further than Kush Fine Art, where Wailea-based painter Vladimir takes surrealism to heart-stopping heights. Souvenir shopping? Skirt the ABCs lining the streets and peruse the wares at Maui Hands—a fine art co-op that presents work made exclusively by local artists.

Brilliant, sensational, and flat-out wow are just three of the ways critics have rated ‘Ulalena. Saturating audience members with the sounds and sights unique to Hawaii, this gripping performance takes guests into the myths at the core of island culture. Grab a glass of wine and prepare to be astonished: This is theater at its finest.

Day 10: Cast Away

Save the best for last? Perhaps. But you won’t know the full range of Maui’s beauty until you’ve traveled to the remote eastern shores of Hana. Soul-stirring scenery beckons beyond each bend on the serpentine—and sometimes treacherous—52-mile highway to this sacred and peaceful town, where emerald cliffs, bucolic fields, and startling waterfalls compete for attention with the cerulean sea. Wander through whispery bamboo forests, snack on succulent mango in Kipahulu, dip into the pools at ‘Ohe’o Gulch, and then break out your towel on the heavenly sands of Hamoa. Valley Isle Excursionssteers the way for those who’d rather eye than drive, providing passengers with an unforgettable tour of one the last relics of Old Hawaii.

Hana adventures
Hana adventures

Those searching for a dose of exhilaration will find their thrills with Rappel Maui. Manned by canyoneering guides that are as spirited as they are skilled, this friendly outfit takes bold voyagers deep into the greenery to rappel down jungle walls and get up close and personal with striking waterfalls.Hiking through rainforests is coupled with swimming in freshwater pools-- reminding adventurers that sometimes there’s nothing more fun than getting down and dirty.

Maui itinerary
Maui itinerary

All photography was either taken by Mill House staff, from owners that have given us written permission, and/or purchased for use. We have all the rights necessary to use these images on our website.