2-Week Maui Itinerary
Last Update on: June 18, 2021

In two weeks’ time, you can make or break a habit, fall in or out of love, sail from New York to England, or bicycle from Seattle to Cabo.

Or you could save up your vacation days and spend two blissful weeks basking in the gloriousness that is Maui.

2 week Maui itinerary

Need some direction with all that time on your hands? Here’s how to savor every minute of your 14 days on the Valley Isle, and fall—and stay—in love with the island while you’re at it.


Day 1: Get a Base Tan & Some Culture

You came for the sunshine, and you’ll stay in love for the same. Fulfill your first wish by hitting up one of Maui’s best beaches.

Wailea’s Mokapu Beach is the stuff of legends. Think talcum-soft sand, water so clear you can see fish without a snorkel mask, and outlying islands resting in the distance like sleeping giants. Located between the Marriott Wailea and the oh-so-posh Andaz, Mokapu offers a stretch of immaculate white sand, green-grassed knolls, and water so warm it’s akin to taking a bath. Spread out a towel and soak it all up: it’s the choicest way to kick off your trip.

And while you’re soaking it up, take a break from your Spotify playlist and catch up on a few podcasts by the Aloha 360. Find out what a perfect trip through Upcountry looks like, hear what’s new with entry regulations, and learn all kinds of other island insights.

South Maui Luaus

Now that you’re relaxed, get ready for dinner and a show at one of our south Maui luaus. We have 3 favorites worth looking into.  The Grand Wailea luau is the most popular, the Wailea Marriott Luau currently has the most availability, and The Andaz Wailea Luau is considered the most luxurious.  Any luau you choose will be a great time for you and your family.


Day 2: Soar Through the Clouds

There’s driving down the world’s largest dormant volcano—as in 10,000-plus feet—and then there’s zooming down on it on a bike.

Exhilaration meets exquisite vistas on one of Haleakala Bike Company’s downhill tours, which takes riders from Haleakala National Park to a serpentine road with outrageously beautiful scenery. Arid volcanic deserts give way to expansive fields lush with local flora, reinforcing why Maui’s moniker is No Ka Oi.

Maui bike rides

Post-sweat, learn a little trivia and taste some pristine swill at an afternoon tour of Ocean Vodka Organic Farm & Distillery. Situated on the slopes of Haleakala, this eighty-acre facility peers down upon sugarcane fields and hyper-blue water, while tours give guests an inside-look at their sustainable approach to producing award-winning spirits. Complete your trip with a stop at their Martini Garden, where locally grown ingredients like Kula Lavender are splashed into vodka cocktails for an inimitable flavor.

Ocean Vodka Maui Tours

Consider dinner done by snagging a table at Bistro Casanova in Kahului. Sultry and intimate, this local favorite has a stellar tapas menu filled with island-fresh extras.


Day 3: Meet Maui’s Wild Side

Birders will be bewitched by grabbing a super-foamy Flat White at Kihei’s Akamai Coffee Co. before taking a sunrise stroll through Kealia Pond National Wildlife Refuge, a seabird sanctuary and natural wetland that houses herons, coots, and Hawaii’s native (and endangered) stilt. The tranquility found within these 700-acres is worth the early a.m. wake-up call alone.

Kealia Pond in North Kihei

Greet more of the island’s incredible biodiversity by making a stop for snorkel gear before setting out to Makena’s Turtle Town for some superb snorkeling. Here, Hawaiian Green Sea Turtles amble by while a host of fascinating fish dart beside them. When hunger strikes, hike up to the main road for plate lunch, burgers, tacos or something else at the many food trucks next to Mauka Azeka Plaza.

Maui painting nights

Inspired by all the natural wonders Maui has to offer? Indulge it at Kihei’s Island Art Party—a fun take on a night on the town that involves learning how to paint a tropical setting you’ll get to show off back home. The vibrant atmosphere—coupled with their local beers, champagne, and wine—turns an island night into something truly one-of-a-kind.


Day 4: Hover in the Clouds

You did a lot yesterday, so let’s keep it to one major activity so that you can take it slow the rest of the day.  Plan to visit either Haleakala, Haiku, or Kapalua for Maui zipline tours. We have an affection for Kapalua becausethe views are so good, but any zipline you pick will be fun.

Maui ziplines

If you do a zipline course, make sure your group is ready to do a little hiking.  The paths are good, but it does require walking to each tower/platform and some require walking up steps.


Day 5: Browse and Dinner Cruise

HOP – While each part of the island possesses its own charm, Maui’s West Side captures the prevailing view of paradise: sugary sand, aqua water, and grove upon grove of coconut palms. Plumeria trees and beachy mansions flank Lahaina’s Front Street before it gives way to rows of shops and restaurants that peer out onto an ocean filled with sailboats and surfers. Grab breakfast at Betty’s Beach Café, which blends tropical tacky with tons of aloha spirit (and sits so close to the ocean you can practically feel the spray from the waves).

Lahaina Town

Pack your swimsuit: right in front is a lovely little beach where longboarders paddle out for the best breaks near the pier and keiki splash in the shallow water. Post-dip, tackle your souvenir shopping—or grab an island memento for yourself—by taking a stroll down Front Street, where jewelry stores elbow boutiques that sell everything from pikake soap and vintage art to luxe candles.

sunset cruise Lahaina

Finish the evening off right: with the best sunset of your life!  What makes a perfect sunset?  Sunset on the west coast of Maui when ON the water, makes for an impressive double sunset (reflection adds quite a bit.) Add a multi-course dinner with quality drinks and live music, and you’re likely on the Maui Princess for their Lahaina sunset cruise.  It might be your favorite meal on Maui.

Day 6: Go Green

Eggs Bennies and Bloody Marys are pretty fabulous on their own; consumed with a breathtaking view and they taste even better. Ease into your morning with a trip to 5 Palms in Wailea—a bright, airy spot that sits on one of Maui’s most impressive beaches.

Once you’re revitalized, head to the center of the island, where you can take your pick between two fantastic hikes. Iao Needle shoots towards the sky in vivid shades of green right above Wailuku town. With its verdant landscapes, misty air, and freshwater stream, the Iao Valley offers guests a glimpse of old Hawaii and enthralling stories of its war-torn past.

Iao Valley Maui Hawaii

For those with more energy to spare, head to Waihe’e Ridge, where an uphill trail through ferns and ohia trees rewards intrepid hikers with spectacular views of rainforests and the ocean.

Desperate for a pick-me-up when you’re pau? Wailuku Coffee Company serves a luscious latte, while those looking for a different kind of buzz needn’t look further than Kahului Ale House.

Days in nature take on a whole new glow when they’re paired with an evening of elegance, so freshen up at sunset and prep for a night out in Wailea. While this chic enclave abounds with excellent restaurants, locals have a soft spot for Ko Restaurant at the Fairmont Kea Lani. Exceptionally fresh sushi competes with awesome zarzuela and Molokai Venison, while the vinos are rare and delicious.

Fairmont Kealani

Keep that romantic mood going with an after-dinner stroll along Wailea Coastal Walk, where tiki torches light a path that parallels the water and takes ramblers to the Four Seasons Resort. Pop into their lobby to be put under a spell: island-inspired cocktails are served with Hawaiian and piano music by local talent.


Day 7: Play Hard

Hawaii is a golfer’s Shangri-La, offering tee-timers ideal weather and views that’ll make even the most serious golfer want to linger. Gear up for a round at The Kaanapali Golf Courses on the island’s West Side, which is consistently voted one of the premier golf courses in the world. You’ll understand why the moment you step foot onto the resort’s well-heeled grounds, where mist-tipped air cradles views of Lanai and Molokai. The option between two courses fits every sportsman’s desire, and apres-round spirits are offered in a clubhouse meant for losing time.

Maui Golf

Still in the mood for a game of strategy? Book an evening at Maui Escape Rooms, where jailbirds, thieves, and shipwreck survivors are offered a list of clever clues to break free from captivity. Once you’re liberated, revisit Front Street to take a tour of the galleries, then close out your day at Ululani’s Shave Ice, a hotspot that offers fresh flavors ranging from lychee to mango.


Day 8: Snorkel then Zen Out

Listen carefully, because this is gold. We’ve done this 3 times so far and will do it again.

Though we’ve gone to Molokini dozens of times, leaving at sunrise is worth hitting the hay a little early the night before.  It’s not hard to get up this early, not like the mainland.  The air is warm and the birds are already singing up a storm. Arrive when the sun is just coming up, walk from the beach directly onto Kai Kanani’s luxury sailing catamaran, then cruise directly across to Molokini Crater.  They have the closest departure point to the famous snorkel spot, so it’s quick.

sunrise Molokini snorkel

Once there, you’ll notice you’re the only ones there!  Enjoy a leisure snorkel session then pop back on the boat for pupus and drinks.

After your snorkel session, spend at least half the day on Maluaka Beach.  This is one of the top 3 beaches in Hawaii.  You’ll thank us later.


Day 9: Discover Paradise

One of the boons of staying overnight in Hana is having a head start on a day of adventure the next morning. Rise with the birds and enjoy a cup of plantation-grown coffee at Laulima Farm Stand in Kipahulu, which offers just-picked fruit, sugarcane juice, and tours of their organic orchard. Fueled up, let the fun begin.

First stop? ‘Oheo Gulch. Otherwise known as Seven Sacred Pools, this natural marvel is a sight to relish: tiered waterfalls, framed by rainforest, cascade into pools that ultimately meet the ocean, with each ascent evoking more of a reason to call this area heavenly. Na’ili’ili Haele—aka Hana’s beloved bamboo forest—takes travelers deep into a space that’s just as holy, with a string of waterfalls and bamboo so thick and dense the outside world becomes impossible to imagine. For a moment of reflection, stop by Palapala Ho’omau Church, a quiet cemetery best known for housing Charles Lindbergh’s grave and that looks out upon Hana’s astonishing coastline.

Palapala Church

When hunger strikes, make your way back to Hana Town, where options range from local kine fare like hot dogs and Spam musubi at Hana Ranch Store to scrumptious fish salads at Thai Food By Pranee. Or gather some picnic goods (and some touristy swag while you’re at it) at Hasegawa General Store, a hundred-year-old outpost that sells everything from fishing poles to books on Hawaiian legends. Koki Beach Park enthralls with its rich cultural history and red cinder hill, while Hamoa Beach is fringed with striking trees and a pervasive sense of old Hawaii.

2 weeks in Maui

For those who faced Hana Highway on their own, discover a new part of the island by traveling the back way home to civilization. Spine-rattling curves give way to vistas of lava terrain and immense expanses of ocean as you meander your way past Kipahulu to the most desolate part of the island. Stretch your legs and enjoy Maui’s bucolic past at Kaupo General Store, where the drinks are cold, the staff is warm, and the scenery seems cut from a different century.


Day 10: Hang Ten

Drive by Kihei’s Cove Park or Lahaina’s Breakwall and a part of you will be desperate to hop out of the car and join the paddlers and surfers. Here, glossy waves roll gently towards shore while the beachy city buzzes in the backdrop, and snorkelers stroll by after splashing in front of Charley Young’s.

Indulge your adventurous spirit with professional Maui surf lessons— lively-manned teams of ocean pros who’ll show you how to stand up paddle with style or surf with confidence.

Maui surfing school

Few sports stir the munchies like surfing—and few South Side spots know how to satisfy your hunger like That’s a Wrap.  Take your fresh feast to Kam III, where a great expanse of grass offers groms the chance to nap under the sun.

Stretch those sore muscles with an evening of Vinyasa at Wailea Yoga Shala, a peaceful studio that offers peekaboo views of the Pacific and seasoned instructors who welcome all levels. Replenished? Put on your party shoes and hit up the Triangle for pre-dinner drinks before slipping into Sansei Seafood Restaurant & Sushi Bar for some amazing eats and late-night karaoke. Singing not your thing? Diamonds Ice Bar & Grill has a certain divey lure, frequent events, and a bank of pool tables.


Day 11: Spoil Your Taste Buds

Skin (and soul) need a respite from Maui’s sunshine? Make your way Upcountry—an often overlooked part of the island that offers a thoroughly new side of paradise.

Begin at La Provence on the cloud-kissed slopes of Kula, where French-informed dishes are served with billion-dollar views. Maintain that panoramic perspective at Ali’i Kula Lavender Farm, a breathtaking orchard that cultivates over 60 varieties of lavender amidst towering bunches of tropical flowers, bonsai-d avocado trees, and peace-provoking statues. Bring a book and enjoy a few hours of quiet at their terrific little bistro, where lattes are infused with lavender and scones come with specks of purple.

 day 11 Maui

Lavish in a different shade of lavender at Ulupalakua Vineyards. Their pineapple-suffused Maui Gold offers a taste to remember, but it’s the house in which the magic happens that ultimately rewards visitors. Over a century old, this is where the last king of the islands gathered strength for a rapidly-changing Hawaii.

Then, descend the island’s slopes to Hui No’eau, a lovely structure that teaches and houses Maui’s many diverse artists; daily tours take visitors across the grounds and past studios. Evening eats ought to be inventive and romantic, both of which can be found by journeying to Nuka in Haiku. Try their Hamachi Carpaccio—it’s as sublime as it sounds.


Day 12: Whale Away

When in season (Dec.15-May.15) visitors to the island are in for a once-in-a-lifetime treat: The cooler months draw Humpback Whales to the island’s warm waters, where the magnificent beasts breach and leap just offshore. Sightings from the sand are something else, but whale watching tours offer close encounters that are nothing short of miraculous. Many boats give oglers the perfect perch to view their awesomeness, but Redline Rafting’s amicable crew gives guests excellent lessons on Maui’s favorite animal.

 day 12 Maui

Back on land, lace up those sneaks and set out for La Perouses’s King Highway in the late afternoon. With origins that date back to the 16th century, this craggy footpath hugs the Pacific and takes hikers to abandoned, crystalline-watered beaches and ancient Hawaiian temples. Tread carefully and keep your eyes peeled: The lava is sharp and sometimes hazardous, but the tide pools offer incredible gems for those willing to pause and ponder.

Dinner calls for an adventure of a different kind: progressive dining, with each venue within walking distance. Start with The Shops at Wailea for pupus at Tommy Bahama’s, lobster cannelloni at Longhi’s, and Kauai Pie ice cream at Lappert’s. Stroll over to the lobby at the Grand Wailea for a nightcap at Botero Lounge, then cruise through the hotel’s extravagant grounds to admire its artwork and search for celebrities.


Day 13: Learn To Fly

There are a few ways to experience learning to fly on Maui.  We’ve tried flying a helicopter, and it was thrilling, but it was so much harder than I thought, and touchy.  I suggest trying a Cessna to start.  Much less of a learning curve, and you get to enjoy the views far more than you do when stressing over every slight movement of the controls.  Fly Maui Hi has the perfect discovery flight where they make it easy to learn and try your hand (quite literally) at flying a plane for the first time.

flying over Maui

Pre-dusk, wash off those sandy toes, and stroll up to Pint and Cork above The Shops at Wailea. They serve a highly-elevated pub menu along with some rare and delicious bottles.  This is one of our favorite spots to eat on Maui.

shops at wailea

Keep the chill island vibe going by seeking out some live, Hawaiian-style music. Nearby Monkeypod Kitchen features local prodigies who know how to enchant in C chord, while Mulligan’s—also close—has a rotating schedule of first-rate entertainment.


Day 14: Helicopter Flights

There’s no question about it: Your final Maui day on this particular stay requires going out with a bang—or, in this case, an astonishing glide.

From the thrill of ascending into the clouds to astounding perspectives, helicopter tours have gone from a niche activity to a leading choice for vacationers. Maui Helicopter tours take voyagers high into the sky to see parts of Maui that shock and inspire. Some tours are known to fly passengers across staggering expanses of Hana, Haleakala, and West Maui.

surfing Hookipa

Once you’ve found your equilibrium, head to Paia, the Windsurfing Capital of the World and arguably the island’s most eclectic town. Here, trendy boutiques with Acacia swimsuits share real estate with Willie Nelson’s favorite local haunt and art galleries brimming with glassworks. Have a nibble at Flatbread Company before hopping back into the car for turtle-watching and sun-bathing at Ho’okipa Beach Park. Still, some sun to spare? Finish off your day with a late afternoon hike at Twin Falls.

Celebrate your last night at Mama’s Fish House in Kuau—one of the finest restaurants on the island with surf so close you can hear it. Happen to be a marvelous night for a moon dance? Let it guide you as you take a late-night beach walk near your resort or condo. Then make a wish upon a star for a return ticket—there’s not a doubt Maui now has a special place in your heart.