7 Day Maui Travel Itinerary for Outdoor Adventures

For those pursuing natural beauty and world-class style, Maui has few peers. And, for the ultimate distillation of the Maui way of life, it matters where you stay and the Grand Wailea, a Waldorf Astoria Resort can’t be beat, thanks in no small part to its membership in Hilton Resorts, a collection of fabulous hotels in spectacular locations, including French Polynesia, Mexico, and the Caribbean. Whether you’re looking for all-age activities at a full-service resort to the very best in modern design and international cuisine at an adults-only all-inclusive property, Hilton Resorts has a destination that will make your travel dreams come true worldwide.

In Maui, amidst 40 verdant acres alongside the sparkling waters of Wailea Beach, the Grand Wailea features the largest private art collection in all of Hawaii, nine pools, and, with a recent spate of upgrades and renovations, the pinnacle of Hawaiian comfort and grace.

“As a resort dedicated to providing the ultimate paradise for our guests, Grand Wailea’s offerings embody the rich culture and history of Maui by way of luxury and adventurous programming, all tailored to the location’s stunning surroundings,” says John Paul Oliver, Managing Director for Grand Wailea. From the remote waterfalls and incomparable views along the Road to Hana to the expressive art galleries and charming boutiques of Upcountry, visitors to Maui will be treated to the very best of both worlds.

“Our focus on wellbeing continues to be influenced by Hawaiian traditions, making Grand Wailea the perfect place for rejuvenation of the body and soul,” he adds. To get that heart rate up, guests have seemingly endless options, from several tennis courts and a 2,500-square-foot onsite fitness center to the three award-winning golf courses nearby.

If you’re looking for the ultimate intimate holiday, you’ll be delighted by the laid-back elegance of the property’s hotel-within-a-hotel, Napua, featuring custom-tailored rooms and suites and the Napua Lounge with a dedicated concierge and private food and beverage services specializing in local, sustainable ingredients served daily alongside a diverse array of live entertainment. And if you’re island-hopping, there are a multitude of Hilton Resorts options to choose from throughout the Pacific, including Hilton Garden Inn Wailua Bay on the Garden Island of Kauai.

Itinerary

PLAN YOUR TRIP

TRIP HIGHLIGHT

Upcountry

The volcanic soil of Upcountry Maui has provided Hawaiians with fertile farming grounds for eons, and a visit to its colorful, otherworldly landscape should prove no less fruitful for any visitor in search of inspiration. From the peak of Haleakalā to the thriving arts scene of the village of Makawao, also known for its unique Hawaiian rodeo, to visit Upcountry is to enter another world entirely.

TRIP DESIGNER

Hilton Resorts

Taking Hilton’s world-famous hospitality to a whole new level in terms of style and convenience, Hilton Resorts has properties spanning the globe, each offering its own kind of extraordinary experience. Whether you’re looking for family fun, a grand escapade, or something in between, Hilton Resorts will exceed your expectations.

Day 1Welcome to Paradise

Once you step foot on the grounds of the Grand Wailea, you’ll be embraced by the tropical calm of its gardens and welcomed by a concierge team devoted to ensuring that you have everything you need to make this the stay of a lifetime. After you’ve checked into your private retreat and have strolled the impossibly lush grounds, grab a Mai Tai at the adults-only Hibiscus Pool, so-named for the 650,000 Mexican glass tiles in its mosaic floor, then soak in one of Maui’s romantic sunsets from one of its two Jacuzzis. If the whole family is along for the ride, the Wailea Canyon section of the resort features four jungle-themed pools, complete with a rope swing, waterfalls, caves, and the three-story Lava Tube Slide suitable for all ages.

Take a tour of the grounds with the resort’s in-house cultural ambassador, affording you the opportunity to taste local fruits fresh off the tree while learning more about the picturesque grounds. Secure a private table for the resort’s famous lū'au, with hula lessons, vibrant music and dance, and a Hawaiian feast with breadfruit salad, roast kalua pork, and a spectrum of seasonal sweets. Oliver describes its “intimate setting” as one that “really brings the cultural influence of the island front and center in a way that is inspiring and authentic. Guests come away informed and enlivened by the experience, and with a more profound understanding of the myths and legends that have been cultivated over centuries on Maui.”

Day 2Into the Wild

Be sure to spend some time exploring the resort’s art collection, the largest of its kind on the island, a veritable scavenger hunt within the resort’s acres of sustainable gardens that include the nine newly-restored sculptures by famed artist Fernando Botero. From there, your concierge can help you book a guided tour of the Hoapili Trail over La Perouse Bay, a rigorous, singular hike across South Maui’s coastal lava fields once reserved for Hawaiian royalty.

Cool off with a splash in the Pacific Ocean at Wailea Beach, just a few steps from your room, and end your evening amidst those larger-than-life sculptures with Japanese-inspired cocktails, whiskey tastings, and a creative sushi menu at the resort’s Botero Lounge.

Day 3A Day in Upcountry

With a short drive to the rolling hills of Upcountry, it might seem as if you’ve entered a portal to another universe, as the typical postcard Hawaiian beaches transform to what looks like a lunar landscape. Here amidst Haleakalā National Park, Hawaiian cowboys called paniolo oversee the hordes of cattle at the foot of Maui’s highest mountain.

Stop by the expressive village of Makawao to explore the charming boutiques of artists and artisans who live there, after which you can grab some pillowy cream puffs from the famed T. Komoda Store, first opened by a Japanese plantation worker in 1916. From there, you’ll be able to visit lavender fields, taste local vintages at MauiWines, and marvel at the 33,265 acres of Haleakalā Crater, home to more endangered species than any other national park in the whole of the United States. For a truly unforgettable experience, your concierge can also arrange for a private helicopter tour of the island, complete with a champagne landing near the winery.

Day 4Riding the Waves

Start your day off with a bit of beach yoga or spin at the Fitness Center, followed by the special Rosé Brunch featured every Saturday at ʻIkena, otherwise home to Grand Wailea’s seaside breakfast buffet. Once you’re feeling sufficiently sated, head a mere four miles south of the resort to Makena Beach State Park where you’ll find one of the largest undeveloped beaches in all of Maui. From that lava-crested cove, a range of activities can be enjoyed, including whale watching, snorkeling, and catamaran expeditions.

Alternatively, head north to Paia Bay, where big-wave surf enthusiasts should have no trouble finding a board to rent and a wave to ride. On dry land, the quaint town of Paia offers plenty to brighten your day, whether with a relaxing beverage at Aumakua Kava Lounge, or by browsing the local art and handicrafts at the beachside boutique of Maui Hands.

Day 5On The Road

The Road to Hana is one of the most famous drives in the world, and the crowds certainly reflect that. Avoid the traffic with an early start and a few helpful pointers from your concierge, and you’ll be treated to a wonderland of waterfalls, bamboo forests, and lava tubes.

More intrepid drivers might consider braving the wild and wilding roads east to visit the Seven Pools of ‘Ohe’o Gulch, beyond which lies the humble resting place of controversial aviator Charles Lindbergh. Gourmands shouldn’t miss the fresh ono and mahi-mahi at Mama’s Fish House, just a pair of miles east of Paia Bay. Mama’s reputation is sterling, and space is limited, so be sure to book several months in advance.

The sunset over Humuhumunukunukuapua'a — The sunset over Humuhumunukunukuapua’a

Day 6Back at the Resort

Golf lovers of all stripes and skill levels can pass the early hours of the day on one of three nearby golf courses, including one that once hosted legends such as Jack Nicklaus and Arnold Palmer as the home of the Celebrity Skins Game.

Enjoy an astrology reading, an aromatherapy journey with the woman-owned, locally owned Lokelani Essentials, or luxuriate in a romantic couple’s massage at the spa. And cap off your day with a dinner alongside a romantic beachside lagoon at Humuhumunukunukuapua’a, named for the Hawaiian state fish. With daily menus featuring sustainable seafood and 90-percent locally sourced produce, including seared ahi with foie gras and kampachi tartare with ginger and smoked ponzu, it will surely be a highlight of your stay.

Day 7 A Fond Farewell

If you haven’t yet, start out your final morning at the resort with a fresh smoothie at Loulu, now offering farm-to-table goods in collaboration with Erewhon, the famed organic grocer. Close out your trip in the embrace of the Pacific with a traditional Hawaiian ceremony called e ala e. “During this beautiful process,” Oliver explains, “guests meet with [Grand Wailea’s Cultural Programming Manager and Leadership Educator, Kalei Uwekoolani] on Wailea Beach for a sunrise-guided Hawaiian oli (chant), through which they relinquish their stress to the calming waves of the ocean to start their days with renewed energy and spirit.”

Thankfully, your newfound bliss doesn’t need to end when you leave the island. Start planning your next trip to the Maldives, Tulum, the Seychelles, or beyond with Hilton Resorts to keep the kind of good times coming that you get with a hotelier that brings more than 100 years of hospitality expertise.